On this episode of “Cocktail College,” host Tim McKirdy dives into a cocktail with an interesting name and an even more fascinating history, the Scofflaw. He chats with Jill Cockson of Kansas City, Mo., owner of Drastic Measures, Swordfish Tom’s, Chartreuse Saloon, and Anna’s Place (Omaha). Tune in to learn more.

Listen Online

Listen on Apple Podcasts

Listen on Spotify

Jill Cockson’s Scofflaw Recipe


  • 2 ounces rye whiskey, such as Rittenhouse
  • ¾ ounce fresh lemon juice
  • ¾ ounce grenadine, homemade or high quality
  • ¾ ounces dry vermouth, such as Dolin Blanc
  • Garnish: orange twist


  1. Combine all ingredients in a cocktail shaker with ice.
  2. Shake until cold and double strain into a chilled coupe glass.
  3. Express an orange twist over the cocktail and drop in the drink as a garnish.

Check Out the Conversation Here

Tim McKirdy: Hey, this is Tim McKirdy, and welcome to VinePair’s “Cocktail College.” Beaming in live, at least live for me, over video and audio for you guys, we have Jill Cockson in Kansas City. Jill, how’s it going?

Jill Cockson: It’s generally terrible right now, but outside of existential dread, it’s going great.

T: I think that’s a very good answer for the times. I’m excited to jump into our drink today, the Scofflaw. I’ll go straight off the bat and say, this is a great name for a cocktail.

J: Absolutely. It’s always been one of my favorites. I always referred to it as the gateway whiskey drink. When people tell me they don’t like whiskey, this is kind of my go-to. I say, “I bet you do.” And this is how I at least try to convince them to give it a try. It doesn’t have a 100 percent record, but it’s got a very high record of convincing people that whiskey might be a category they’re into. They just didn’t have a drink they like yet. So it’s a nice, easy intro to whiskey, which is really nice. And obviously then given the context of right now and what we’re going through. I think there’s a great parallel as to how that drink was developed and the sentiment of the time during Prohibition versus right now as Roe v. Wade is being dialed back and we’re coming up on some interesting times.

T: Yeah, definitely. And I think as you mentioned there, this being one of those ones that we can discuss on this show that actually does have a rich history or is pretty agreed upon one. So can you give us the context there? Can you outline that history and tie that line through it?

The History Behind the Scofflaw

J: Sure. In my understanding and my research — and please feel free to add to this — is that the cocktail was developed by a bartender at Harry’s New York Bar in Paris during Prohibition. The story goes that most of the professional bartenders during Prohibition either left the country, found work in other countries, or found other work sometimes as writers. But we almost lost our lineage of our profession during Prohibition because there just simply wasn’t legal work for them. So the bartender at Harry’s New York Bar in Paris basically offered the cocktail as an homage to people in the United States who continued to drink despite the laws of Prohibition. And so that extra layer of being in Kansas City, and ironically we’re called the Paris of the Plains; we have the second most public fountains next to Paris, France in the world. So we are known as the Paris of the Plains. So there’s a lot of ties to this cocktail culturally. And also, Kansas City historically is the only city that did not experience Prohibition in the United States. It was very mob-driven and organized crime-driven. And the person at the helm at the time was a gentleman named Tom Pendergast. He made sure that liquor kept flowing in Kansas City during Prohibition. He opted out, like, yeah, we’re not doing that.

T: So people were resisting there. We were chatting a little bit about this beforehand because I believe, historically, there is an alternative universe where you and I are covering this drink on this show, but instead, the drink is named the Boozecrat or the Boozshevik. Because I was doing a little bit of research here. Obviously, like you said, Scofflaw is this idea of people scoffing at the law. I’m going to really ruin the pronunciation of this, I’ve Googled it, but there’s a gentleman named Delcevare King. I’m probably ruining it. Basically, he’s a banker and a Prohibitionist from 1923 Massachusetts. He sets up a competition. He wants to invent a new word, and the word is used to describe people that are lawless drinkers. So he sets up a competition with a $200 reward for that competition, receives 25,000 entries, and “Scofflaw” is the one that they land upon. So I think there’s that whole irony there, too, as well. Not only is it a bartender in Paris that has left the country to pursue bartending, but specifically in the beginning, it ultimately related to drinks, too. Which is great.

J: Oh, yeah. Thank you so much. I actually did not know that extra layer of the history of that drink, so thank you.

T: Yeah, I found that in some kind of New York Times time machine. They’re out there. It’s fun. It’s amazing. But either way, just off the top, like I said, it’s a great name for a drink. And also, I’ve got a question for you. Actually, can you briefly just describe the ingredients for those who aren’t aware of it? We don’t need to go too much into it, but just list them, because I think this isn’t one that most folks are aware of off the top of their heads.

J: When I describe this drink to people to make it relatable to them or if someone says, “I don’t like whiskey,” or “I’d like to try whiskey, but I don’t know what you try first,” I say, “I have the perfect cocktail for you. Think of it as a pomegranate whiskey Cosmo.” I mean, it just makes it relatable. They know the word Cosmo. They know that there’s going to be something fruity about it. It’s not going to be super scary. And essentially it’s rye whiskey, dry vermouth, lemon juice, and then the key is real grenadine. I think there are a few drinks that disappeared from the landscape of menus, precisely because when we went through the Food Industrial Revolution, a lot of people switched to industrial and commercial mixers. And grenadine was one of those casualties, that red stuff that you buy in the bottles. It’s not grenadine. I don’t know what it is. Most people think it’s supposed to be cherry. It’s not. It’s supposed to be pomegranate. And the red dye in them or whatever the bottle that you normally would see in bars is not the real deal. It makes for a very different and terrible version of this drink. So the key is you need real grenadine, and it’s not hard to make it all. Essentially, if you buy one of those little palm bottles of pomegranate juice, you’re just making a simple syrup. It’s that and sugar, 1-1. So instead of using water in a simple syrup, this is pomegranate juice. And some people choose to add some spices to it, maybe a tiny bit of anise or baking spices. You can add some flavor to it. But really, the key ingredient is just that real pomegranate syrup.

T: Pomegranate juice is not something that I find myself shopping for very often. Perhaps I should be. But is that something that’s quite easy to come across, or is it more of a specialty ingredient?

J: I think over the past 20 years, it’s become more and more common. I think any major grocery store is going to carry that specific brand, that POM brand. If you’re looking for specialty, already-made, real grenadine, you’re going to have to look for a specialty store. A really high-end liquor store might carry it. Or you’ll find it online. But I would say that POM is really easy to come across. It’s 1-to-1 with that and sugar, and that creates your pomegranate syrup. And like I said, you can play with that, add any flavors that you like, but that POM is very easy to find.

T: To be clear here, I think the bartending community has made amazing strides in basically making as much as possible as they can in recent years. But I’m assuming there’s no one out there that’s trying to make their own pomegranate juice. This is not a fruit that’s very easy to work with.

J: It’s so funny because one of the first places that I worked at had a full kitchen; I don’t even remember what drink I was doing, but I was using pomegranate seeds or something. That job was so great because those kitchen professionals were very sweet. They’ll watch you, people like myself, who don’t have real kitchen experience. They’ll watch me do something miserably for two or three times just so they can get a chuckle among themselves and make fun of me. I mean, they’re trying to peel the seeds and I’m making a mess. And about the third time, they’re like, “OK, the joke’s over.” They’ll come up to me and say, “Hey, do you want to do that easier?” It was great to work around people who could show me the tricks of things, like even just getting the seeds from the grenadine. There are tricks to it. I feel like kitchens have secrets that they don’t share. And it’s fun when they let you in on the secret to make your life easier. So yeah, I would not say make your own pomegranate juice. That sounds terrible. I’ve never tried that. I think sometimes our industry goes down these complex processes for bragging rights. It’s like, “Oh, we make our own pomegranate juice.” There’s already a company doing that that does it really, really well. We got a really good product, so just buy that product. You’re going to end up with that product and if you consider the labor, it’s going to cost you about 400 times more than it. Just do it.

T: Good to know your limitations, absolutely. In terms of the modern landscape, I love that this is a drink that you’ve brought up because I feel like this will be an introduction for some folks. Like we mentioned before. Just to share a small anecdote, I was in a bar recently with a group of drinks writers. It was a rye whiskey event and they were making classics and I ordered a Scofflaw. And I don’t think anyone, or a couple of people around me, had ever had one. But then the bartender knew the specs straight away. This is wonderful because I’m sure it doesn’t get called out a lot. And everyone loved them. But from a guest perspective, do you think this is one that ever gets called out, ever gets ordered?

J: I would say it’s been called out more in recent years. It’s funny because there are drinks that never got called out, especially just given the context. If you walk into a cocktail bar, I wouldn’t expect my local neighborhood dive bar bartender to necessarily know how to make it. If I walk into a bar that counts themselves at all as a cocktail bar, I would say that’s one that I would expect to be in the canon. We get it called out at our cocktail bar occasionally. Just depending on context, it’s one that’s made its way up there. If you consider yourself a professional bartender, there’s a certain number of drinks I think you should just have in your repertoire. And I think I think that’s one of them.

T: This is one of them. Fantastic. If it’s not, the ingredients will be at most serious cocktail bars. I mean, generally speaking, these are ingredients we’re familiar with. The formula probably looks very familiar, too, apart from maybe the dry vermouth, which we’ll get into. So I’m just curious to hear what you’re looking for when you make this drink yourself or if someone makes it for you, profile-wise, balance-wise. Where is this on the spectrum?

J: I guess it depends on who I’m making it for and what I’m trying to accomplish, even in the individual interaction. If I’m just trying to introduce someone to whiskey or told me that they’re just trying to go into whiskey and they want an entry-level thing, I might make it a little softer. Especially when you’re in the bar or the commercial setting, is there a need to make it in the original spec? That’s a 2-ounce solid core of a rye. If I was making it for me, I would use a Rittenhouse or something that is going to really drive that backbone. But if I’m going to make it for someone who’s just trying to get into whiskey, I might go to an Overholt or something that’s a little softer, that’s a little higher corn content, it’s a little bit sweeter. I think the drink should drink a little bit more tart. So the normal specs, like I said, called for a 2-ounce of the rye and then in theory, a half-ounce each of lemon, dry vermouth, and pomegranate syrup. I usually soften it a little bit. If I make it in the bar setting, I usually go an ounce and a half of the rye, depending which rye I use. And I usually go to three-quarter, three-quarter, three-quarter. It just makes it a more approachable drink. It might not be the original spec. Something we need to remember is that when some of these drinks are made, depending on what rye they were using, you kind of have to adjust the taste and you also have to adjust to what the guest wants. I think that’s something that’s gotten lost. Our obsession with recipes leaves out what a customer likes. I think the Last Word is too sweet by itself. I will edit that a little bit, but I always ask the guest, “Do you like things a little more sweet or a little more sour?” The nice thing about using all fresh ingredients is you can tip that recipe. We should be listening to our guests because at the end of the day, it’s about creating something that they’re going to enjoy, not making the drink we want to make.

T: Hearing you describe that upping those three components to three-quarter of an ounce, is there also body coming into play here and texture? Can it feel maybe slightly thin?

J: If you’re making a really flavorful grenadine, it all goes back to which dry vermouth you’re using. Obviously, we’re using fresh lemon juice, that’s not an option. This is definitely one of those cocktails where you need to use the real and fresh ingredients. It’s just not going to work otherwise. It’s getting the balance right between the individual components. I think that when you up the grenadine content a little bit, when you add three-quarter, three-quarter, three-quarter, you maintain the balance between the individual ingredients. But that viscosity picks up just a little bit to make that mouthfeel a little bit less like a Manhattan. It’s got some stuff going on. Also this is one of those cocktails where the garnish, the fresh orange twist on it, really seals the deal. It’s nice if you wanted a flamed orange twist, that’s a show. You don’t necessarily have to. Just those nice citrus oils sitting on top of this drink, and that aromatic and that bitter orange oil truly does serve as the bitters to balance this cocktail out. It really seals the deal. So I would say this is one of the cocktails, too, where the garnish is just as important as the actual ingredients.

The Ingredients Used in the Scofflaw

T: I mean, you’ve given us some wonderful oversight of the ingredients there. We will dive into each one now in just a little bit more detail, starting with that rye whiskey. So first question: This is definitely not one where you decide between rye or bourbon. Do you think this should be definitely rye?

J: I personally think it should be rye just because it adds a little flavor layer of spice as opposed to the bourbon. This is already sweet. If somebody did request it with bourbon, I’d have no problem making it. What I would probably do is dial back the grenadine just a little bit because there’s already some sweetness coming from that bourbon.

T: Wonderful. And you mentioned the rye content there, Rittenhouse obviously being more spice-forward and maybe Overholt being that Kentucky style these days — at least not not classically, not historically. How much are you thinking about proof, though? Does Rittenhouse sit at 50 percent ABV?

J: Yeah. That’s what I lean on. I love Heaven Hill, and that falls into their portfolio. I like Rittenhouse because those bonded whiskeys, in my opinion, are a perfect proof to carry the backbone of a cocktail. For example, a Sazerac is originally Cognac. But we’ve learned that the adapted version is with rye. I usually ask people what they want. In my opinion, rye does a better job of carrying the weight of the other ingredients. It just seems cleaner. It adds a spice component. And I just think rye is the more traditional spirit to use and carries the balance of the cocktail better.

T: Wonderful. Next one we’re looking at here: dry vermouth. First of all, dry is the one you’re going with. What are the preferred brands here that you’re looking for, I guess from a flavor profile standpoint, but also realistic working behind the bar bottom-line, that kind of thing?

J: This is one of those cocktails where honestly, because there’s so many other ingredients going on, we can probably spend hours talking about what obscure vermouths every craft cocktail bartender is into these days. But again, if you’re trying to make something approachable, I’m not going to send people on a wild goose chase to go find some obscure Spanish vermouth that one liquor store 30 miles away carries. So this is one of those cocktails where I’m happy using Dolin Dry. It’s fine. I’m a big fan of the Ransom vermouths. I really dig them. I love that they list all of their botanicals on their label. And so you can pick out which of those ingredients or which of those botanicals to enhance or suppress. So if you did want to get a little more creative and make a grenadine that maybe featured some of the botanicals that Ransom tells you is on their label, you can start playing with bringing some of those flavors a little bit more. But that’s not necessary. When it comes to making things approachable, whether it’s for college kids or it’s people cocktailing at home, let’s not make it complicated. Let’s go with something I know they’re going to find at every liquor store they go into.

T: Amazing, and wonderful product as well. It’s a really great vermouth. You were speaking about if you’re asking someone whether they want something that maybe leans sweeter or more sour or more dry. I’m wondering, is there a way in which you can switch to bianco vermouth for this rather than upping the sweet component, the grenadine, so you maintain that balance for someone that’s looking for a sweeter version of the cocktail.

J: Yeah. I like the Cocchi Americano a lot, because in there you get kind of a sweet start. But it doesn’t get too sweet because it’s a quina. It’s got that cinchona slightly bitter finish. So that’s one that I will reach for a lot to play with. And that’s really the beauty of these cocktails. I always tell people, the dirty secret is there are only seven cocktail builds on the planet. Once you understand the templates, then you can start playing with your knowledge of actual ingredients and different spirits by category. You switch out the sweet component or you switch out the bitter component, or you switch out the base spirit. Now you’re just playing Mr. Potato Head essentially with the seven cocktails that exist. So absolutely, that’s definitely an option.

T: I love that suggestion of Cocchi Americano. That’s one I really want to try very soon. That sounds wonderful. Lemon juice, fresh is best. This is one that comes up a lot on this show. I think we’ve said a lot that we need to say about lemon. But any additional thoughts you have?

J: No. Except, for sustainability purposes — again, the clientele of people just wanting to get into it, just keep it easy with fresh lemon juice. I like to use lemon juice within three days. I mean, I know we could go down some rabbit hole of perfect oxidation, acidity, elevation, whatever the nerds get into these days. You do want to keep it fresh. I would say lemon juice is probably best. It starts to get funky, I would say, after three days. Keep it refrigerated. I will say that you know that a movement we’re moving toward a little bit is the concept of super juice. One, given the cost of citrus. And two, just consciousness of the availability of citrus and sustainability of product availability in different regions of the country in the world. Citrus doesn’t grow in the Midwest, it really shouldn’t even be here. How do we start talking about responsible programs that offer fresh ingredients responsibly? If you Google search “super juice,” there’s some really great citric acid oleo recipes that enable you to make a fresh lemon juice substitute that does work. I mean, I won’t say for sure that it works in every cocktail equally, but it’s cool to mess around with it. So if we have some cocktail nerds out there that are wanting to try something, it makes it actually a little more shelf-stable. You can use a little bit more a bit longer.

T: Yeah, win-win there. That’s great. It’s certainly something that I’m starting to see more online or hear people talking about more. And like you say, in terms of sustainability and also just cost of ingredients these days, that’s definitely something people should know about. I think it’s the first time that’s been brought up on the show, so thanks for mentioning that. Next one, grenadine, of course. You’ve mentioned that. So we’re talking about pomegranate juice, normal sugar, 50-50. Can you mention some of the ingredients for this cocktail specifically that you might be tempted to also infuse in that syrup, just if people wanted to go a little bit extra?

J: Whether you would use it in the syrup or you do it as a mist or spray on top, I always think of the Corpse Reviver #2. It has that nice absinthe little note in very small amounts. I know that the flavor of black licorice is very polarizing, so it might be something you don’t want to mix into your grenadine. But you can have a little dropper bottle of absinthe on the side that you just put a couple of drops on the top, so those who want to experience a little extra flavor, great. But you’re not not limited to everybody having to have that, if you have people that just absolutely hate that flavor. You have to be careful with it because It’ll take over quickly so that’s one of those things. Cinnamon might be a nice little add-in, or some baking spices. I think that those are all those flavors that go really well together with the pomegranate and the orange and the whiskey. There’s a way to have a lot of fun. When you boil that grenadine, just to dissolve that sugar more quickly, you can play with those botanicals and those spices. And I just think that’s one of the fun areas. You can find a lot of ways to adapt to the flavor profile of a cocktail very subtly. But it changes the profile in a really interesting way.

T: I guess it also really comes down to whether, from a bar’s perspective, you’re creating that grenadine for this cocktail only or a number of different ones that you’re going to use it in. Actually, that bar that I spoke about before had a grenadine proprietary one and they mentioned it was for a different cocktail. It had some rosemary in there. It actually worked really, really well in that Scofflaw. It’s an interesting thing. Also I love that tip of absinthe because absinthe and rye are great friends.

J: I think that’s a great point. You don’t want to limit yourself. I like to make my grenadine completely plain for this exact reason, because it depends what cocktail I’m making with it. And then I can adapt. I can add a tiny bit of absinthe to the mix, or I can make it clove-studded orange peel. You get the aromatic flavor of the garnish, or you can garnish with rosemary. So you can get those flavors from the garnish, the aromatics of the garnish that you play with without having to adulterate your grenadine and now you’re stuck with this one flavor. OK, great, it’s rosemary grenadine. But now I’m stuck with rosemary grenadine and it’s not as versatile. So I like to keep my syrups pure and then do add-ins and garnishes for additional flavors.

T: And in that vein, and another ingredient I have here, but I know it’s not always used, but I have seen it in recipes are bitters. It’s certainly an avenue for customization. But is that something that you would include classically or not?

J: Oh yeah. There are so many right now. We have a little bit of a problem. The first thing that comes to mind is Scarborough Bitters by Bittermens. I think bitters is one of those categories that people get nervous talking about because they assume that it’s going to make my drink bitter. And one of my best friends, I think, has the best spiel about how to understand bitters in cocktails. The bitter part of our tongue is kind of the fulcrum of our tongue. So when you add a couple of dashes of bitters, it doesn’t necessarily make the drink bitter overall. It pulls the flavors together to balance. If you’re running the risk and it may be a little too sweet or a little too sour, you add those two dashes of bitters. One of my favorite classics is a Fitzgerald. It’s so simple: gin, lemon, bitters, and done. And it is one of the most refreshing summer drinks. It turns a gin lemonade into a totally different thing. Angostura is just a good go-to. You can find that at any liquor store. So I was suggesting to college folks, “Hey, don’t be afraid to grab a bottle of Angostura bitters and just add a couple dashes and see what it does to a cocktail.” But then there’s a whole world of bitters out there; you could add a million flavors just based on the number of bitters. Scrappy’s is one of my favorite, Bittermens too. Everything by all of those lines are wonderful.

T: Amazing. And just to clarify, though, in your version of this cocktail or the recipe that you subscribe to, you’re not reaching for bitters?

J: I’m not reaching for bitters because I’m relying on the bitter oil of the orange as my bitters. So there is a bitter agent. That’s something that I think people don’t realize, and it’s a good, healthy citrus expression. There’s a bitterness to those oils. It’s also one of the reasons that a lot of times you’ll see bartenders line the outside of the glass. If I ever line the outside of a glass with those oils, I make sure to do it underneath the glass because those oils are very astringent and bitter. If you rim the glass with it and they put the glass to their lips, those oils get on their lips and they can actually kind of burn. Not to be dramatic, but it’s very astringent. So you want the aromatic but you don’t want necessarily the overpowering, bitter taste on the rim of the glass. You want that just to be a subtle bitter agent in the drink.

T: Amazing. Are you always flaming this orange expression?

J: If I’m in service, yeah. It depends. Sometimes, we have to choose the practical thing during volume service. If the guest is standing in front of me and they get an added value out of watching that get flamed, great. That kind of caramelizes those oils. If it’s going to a server who is sending that drink out to a guest and they’re not going to see the show, why waste the time? As long as you’re making a good expression and you’re making sure those oils are getting in the drink, it’s going to do its job.

How to Make Jill Cockson’s Scofflaw

T: Fantastic. To tie up all of those things together, can you outline this preparation from start to finish, including ratios and preferred ingredients and brands? Take us through your version of this cocktail from start to finish, please.

J: Like I said, I amend the recipe just a bit. Personally, I would reach for probably a Rittenhouse Rye. That’s also pretty easily findable. But what you’re looking for is high rye as opposed to a sweeter rye. Two ounces of that, mixed. If you don’t have a shaker, you can use a jar with a lid. This is a cocktail you’re going to want to shake. The general rule of thumb that everyone knows is that if a cocktail contains citrus, you shake. If it is an all-spirits cocktail, if there’s no citrus involved, you stir. We could go down a different conversation line about why, but really, you’re looking to get the proper dilution. The shake gets the citrus to bind to the cocktail so it stays in suspension when you pour it. We’ve all had a glass of lemonade that sits on the glass or sits on the table and then you just see the lemonade sink and the water sit at the top. A proper hard shake will make sure that drink stays in suspension and the first sip tastes like the last sip. Nothing sticks to the bottom. So that said, in a shaker of sorts — whether you have an official shaker, Boston shaker, tin shaker, or just a jar with a lid — fill that with ice. People will say that you should always add all your ingredients first, then add the ice. That’s one of the technicalities. During service, I’ll admit that I don’t care. If I’m in a competition, fine. But just know that that’s not that big of a deal. Fill your container with ice. Then 2 ounces of rye. I go with three-quarters of an ounce of fresh lemon juice, three-quarters of an ounce of real grenadine and three-quarters of an ounce of, in this case, Dolan dry vermouth. Put all those ingredients together, lid on, get a hard shake. A good 15 seconds, shake it like you mean it. It’s normally served up, and that just means without ice. And it doesn’t matter. If you’re at home, you can put it in whatever you want. If you want it on ice, drink it on ice. Drink it how you like it. Traditionally, I would double strain that. I would put that through a finer straighter just to get those ice chips out. That prevents the cocktail from getting further diluted in the glasses as ice chips melt. But again, you don’t have to worry about it at home. And then I would finish that cocktail off with a good expression of a fresh orange peel; squeeze gently so that those oils go out over the top of the drink, twist, and drop it in. The end: the Scofflaw.

T: So that garnish is being included in the drink there, we’re not talking a discard situation?

J: You could do either. If I’m serving it, I’m assuring that they’re cleaned up real pretty. You can put it on the glass. That’s another fun thing you can play with if you know how to put the orange twist in. During Covid, we actually shied away from putting anything that touched our hands in the glass.

T: Smart.

J: That’s something that you can think about. If you’re just making it for yourself, it’s one thing. If making it for other people in a service setting, you may consider whether you’re touching that garnish. It’s fine just to express the oils and then toss that garnish off to the side or in the trash so that you’re still getting the aromatic and the bittering agent without having to drop something that you touched with your hands in the actual cocktail.

T: Wonderful. And what would be your preferred vessel here? Just a classic coupe?

J: Absolutely. Again, I know that not everybody has those at home. It’s fun to go to antique stores. They’re kind of around and you can find some fun vintage glasses. We use all authentic vintage glassware at one of our bars, and that’s one of the things I spend my time doing, is going to flea markets and antique malls and even thrift stores and finding fun glasses. That’s a fun part of the process, too. But at the end of the day, it doesn’t matter what you’re drinking out of. If you’re having a good time and you’re with people that you’re having fun with, make that the focus.

T: But that vintage glassware is certainly good for this. It takes us back to 1924, Harry’s Bar there, in theme with the original cocktail. Before we move on to the final section of the show here, Jill, I’m wondering if you have any final thoughts on the Scofflaw itself.

J: Like I said, looking back over my career, it took me longer to discover that cocktail than it should have, first of all. I think that grenadine is the issue, but I think it’s gotten more popular and more common. That’s what you can kind of use as a litmus test. If you walk into a cocktail bar and the person knows how to make it, you know you’re dealing with somebody who probably has at least a decent knowledge of cocktails and you can trust them a little bit. Sometimes I think people call out those drinks as that test. What they’re really doing is establishing a sense of trust with you. Do you really know what you’re doing or not? I mean, it’s slightly obscure, but it’s just well known enough that I think it establishes that I know what I’m doing back here.

T: It’s so funny that you mention that because again, that scenario happened recently this week. It was a rye whiskey event. So on the one hand, I knew we were doing this recording and I wanted to have one. I wanted to have one professionally made. So I thought, “Well, you know, this is perfect.” On the other hand, I did feel like, “Do I just look like a bit of an asshole here because there’s drinks writers and it’s a rye event?” I definitely wasn’t testing the bartender in any way. I was like, “If it’s possible, I would love to try one.” I love a Manhattan, but I’d love a Scofflaw right now.” It was also very hot, so this was the perfect occasion.

J: Just to add a little bit, I would say to aspiring bartenders, it’s important to know your canon. It does establish a sense of trust with people. If somebody comes in and they ask for a Gin Pearl, let’s say I’m working at a bar that maybe doesn’t have absinthe or doesn’t have mint or one of the ingredients, I can say, “Hey, I know that you’re looking for this. I can’t make an exact thing here, but now I know what you’re looking for and I can make something similar,” you can establish a sense of trust with people. Psychosomatically, that will lead to them enjoying the thing that you make because you now establish this bond with them. So it really is important to have that working canon knowledge. Now when people come in, you’re just making that interaction a lot easier. “Well, this is what I normally like.” You’re speaking their language, they’re speaking your language, and you can communicate more quickly about what it is that they actually are going to enjoy and you can get them something quicker.

T: That’s such a great point as well, that idea of understanding drinks or knowing drinks. Even if you’re pretty much aware that you might never make them, chances are there will be something in a similar realm on your menu or on previous menus that you know the specs for.

J: Yeah. We get calls for Death in the Afternoons a lot in one of our bars, and we don’t carry any beer or wine or bubbly. We are a strictly cocktail and spirits bar — no beer, no wine, no food. So we don’t have bubbly there. Somebody asks for one, they say, “Oh, can I get a Death in the Afternoon?” As soon as I say, “Hey, I can’t because we don’t carry Champagne, but I know that you’re looking for an absinthe cocktail. Do you trust me to make you something different?” It immediately bridges that gap. OK, cool. She knew what that was. Now she knows what flavor profile I’m going for. We can get you there.

Getting to Know Jill Cockson

T: Amazing. Thank you very much. I love that. I love that little exploration there to round out the Scofflaw. Now we’re going to head into the final part of the conversation. Feeling good for our five questions?

J: OK.

T: Let’s kick it off, and let’s kick it off with question No. 1, of course: What style or category of spirit typically enjoys the most real estate on your back bar?

J: That’s an interesting question. I would say it’s shifted in the past year. It depends on who’s spending the most time working service. I want the bartenders who are working the most service to be in front of products that they’re excited about selling. I would say that as I stepped away from Swordfish over the past year and put that in the hands of very capable, very awesome other bartenders, they have different loves than I do. So right now, I’ve got rum and agave nerds behind the bar right now, and they’re going nuts. I want them to have what they’re excited to sell, and those two categories enjoy the most real estate right now because of that. Our bars are kind of outliers because we have such limited shelf space per category. Our product philosophy is a few things. We want the category well represented along the full spectrum without redundancy because we just don’t have the shelf space to have three of the same thing. In the agave category, for example, we might only have one by one particular brand. I don’t have room for four of them, but I will pick the one that I want to represent that agave category. It’s the same with the rum. It’s the spectrum flavors in the rum category, just no redundancy. I would say right now it’s those two that occupy probably the most. Whiskey is a broad category, obviously. You have your subcategories. But the thing that I’ve learned the most is that there’s no one product that you absolutely have to carry. There’s a chance to talk to people about new products and get people turned on to new things. I love that the mezcal rise has oddly opened the door to Islay Scotches. Islay Scotch has kind of trailed behind getting people on board. And now that people are less afraid because of the giant mezcal movement, that smoky isn’t scary anymore, you can start walking people into other categories through their comfort zones. They don’t realize, “Oh yeah, this really isn’t that much of a baby step out from this category.”

T: This just came up yesterday because we’ve been doing a lot of rum tasting here at VinePair for some articles we’re working on. I had a couple of Agricole Rhums yesterday that I was like, “Wow, this could be mezcal in a way.” I wonder if that is a natural progression, because I think it’s a hard sell straight away. But folks are more comfortable with exploring mezcal these days, and whether that could be the next stepping stone. I’m not sure how you feel about that.

J: Granted, I’m sure that there’s probably a show coming up for you about sustainability of mezcal. Unfortunately, agave is not a sustainable product. Sadly, we’re seeing this giant rise in demand for it, but just knowing that you’re watching a train wreck happen in slow motion. This isn’t going to end well if there isn’t some real dedication and work done to preserve the integrity of the quality of the product. So that’s another thing to look at. I don’t need to have every agave spirit under the sun because I think that there’s not a lot to go around. We should work to be conscious of maintaining cultural production of products in a way that represents the history of the products, in addition to the availability of that product. I think you could ask the question of, is it even responsible to put a bunch of mezcal cocktails on the menu and to over-promote it when we know that it’s going to lead to probably not great things?

T: Yeah, for sure. Definitely important questions that we need to be having these days and going forward.

J: Yeah.

T: Question No. 2 here: Which ingredient or tool do you think is the most undervalued in a bartender’s arsenal?

J: So I thought about this, and my answer is probably not what you’re going to expect. Honestly, self-awareness. The tools are one thing. Knowing how to use your tool and your fancy shakes, whatever. If I see blunders behind the bar, that makes me cringe. It’s not knowing how to use your personality to do your job professionally. Self-awareness, paying attention to the dynamics going on in conversations, knowing how to be present but not over present. How not to monopolize people’s time. They didn’t come in here for a history on the obscure rum or mezcal or whiskey collection that you have. Shut the f*ck up and get out of their night, you know? That is a skill set all in its own that, and I don’t I don’t know where you start to teach that or what seminars we have. We do a really good job as an industry getting people really excited about products and excited about the newest gadget that they have. “Go look at these bar spoons or these stirring vessels or whatever.” And at the end of the day, the one that makes the most impact on people’s experience is your personality across the bar. I could teach anybody to make drinks. I can’t train you not to be a douchebag, I guess. Do you want to make money? Do you get the people come in here to not be made to feel stupid because they don’t understand your obscure vermouth collection? So I would say the most important tool any bartender has is learning how to use conversation, politeness, and etiquette. Even when you’re cutting someone off, the art of the polite “f*ck you” is a really big tool to have in your arsenal so that you’re never escalating a situation. One of my favorite lines if I’m cutting somebody off is, “Hey, you know, I really want you to like me tonight, but I’d love for you to love me tomorrow. And you’re not going to love me tomorrow if I serve you another drink. So, let’s have some water.” There’s a way to do it tactfully that doesn’t make them embarrassed. It doesn’t cause a conflict. Personality and using your self-awareness across the bar, I think is the most important tool we need to learn how to use that is amazing.

T: And I love that. This kind of blends into the next question, but I love that those are lines for sure that you probably pick up along the way. But I was just curious about the idea of self-awareness. Is that something that you feel like you went into the industry having a good grasp of naturally? Or is that something that developed over time? Is that something you were conscious of developing over time?

J: No, in fact, I’m horrified when I think back to my baby bartending days because I had no mentors. I’m 46; this will be year 25. When I think back to some of the things I said across the bar, you learn the acts. It is an entertainment gig to some extent. But I definitely had cringeworthy things across the bar that I’m looking back on and I’m embarrassed of. I wish I had had mentors back then that told me, “Hey, maybe learn to shut the f*ck up. Maybe learn to walk away, maybe learn to understand hospitality more holistically.” We’re here to host memories. It’s not the “me” show. This is not about me. I’ve had really incredible specific memories that made me turn that corner. And I remember I had a couple one night sitting at my bar who told me that they have a special needs child and they very rarely get to go out because babysitting is very difficult for them. They have very few people who are qualified to care for their child that they trust when they go out. They get to go out about twice a year. And the fact that they chose my bar to have that little alone time that they get as a couple who has the very important job of raising a special needs child was such an honor. I’ve hosted people who are terminally ill and their friends brought them in because this is the last memory they’re going to have together. We forget that not everybody’s out to party. Sometimes it’s like, “Hey, we’re trying to keep our marriage together. We got three kids at home. We only get to go out once every three months.” And if they choose your space, respecting their time and their privacy and knowing how to read the interaction and how much do they want you involved in this night, is something I’m still learning. Sometimes I have friends who come in as couples and I balance that. They’re my friends, but it’s still their date night. If they sit at the bar that gives me the OK, they want to have more conversation time. But if they go and sit at a table, that’s their subtle message to me. They don’t want me hovering over them. They came to support my business, awesome. But they didn’t come in here to see me. This is their date night. So I think those are areas that we can all become more self aware of.

T: Thank you for sharing, an amazing tool is self-awareness. I love it. So definitely out of left field, but very, very useful. Thank you for that one. Question No. 3 here: What’s the most important piece of advice you’ve received while working in this industry?

J: Gosh, a lot of things. I thought of a lot of things when I read that question. It’s going to be extended to my field and it’s funny. One of my old partners helped me start The Other Room and I’m so thankful for him. When I opened The Other Room, I was not a majority owner. And I don’t think he realized I was listening at the level I was when he said this thing, but it will never leave me. And he said, “There’s two ways to get an education. You can go to college or you can be a minority partner.” I’ve told people that now as I’m trying to help more people achieve ownership status and coaching them into those ownership roles and helping them negotiate ownership roles with partners. If you do want to make the move into ownership, if that is your long-term goal of your long game in this industry, I think that has been the most mind blowing. You start learning the rules of corporate arrangements and partnerships, it doesn’t matter if you’re an 49.9 percent owner. You can get voted out. You can be eliminated some way, somehow. So developing the skill set of negotiating a majority ownership position if your goal is to become an owner someday. I would say personally, that resonated with me in a way that he probably isn’t even aware of. We’re still friends, I’m still involved in The Other Room in Lincoln, Neb. It is my baby. I will always do everything I can to make sure that it survives. I moved on to do my own thing. And honestly, my partners there were just really influential. I was listening in ways they didn’t realize I was. In my personal career, that’s my biggest piece of advice. Always be a majority partner.

T: Amazing. Thank you. That’s some great advice right there. Question No. 4, penultimate question: If you could only visit one last bar in your life, what would it be?

J: I came up with that answer in answering question No. 2, I think. I have yet to go to Kumiko in Chicago to see Julia Momosé. There are different parts of our operations of service. But if I had to choose one person that I can personally take every bartender to to watch work, it’s her. She is someone who I believe personally embodies hospitality in a way that is truly artful. I don’t say this in a stalker, obsessive sort of way. Julia knows I’m a huge fan of hers. I just would love to see her behind that bar. I’ve seen her work in other places. I have yet to see her work at Kumiko, and I firmly believe she’s in her home place. She’s someone who just mastered the art of being exactly where she needs to be, when she needs to be there. She is just on as a dedicated hospitality professional. I’ve never seen her out of this mode and it’s like she appears from nowhere. You think you need something and then there she is. She has a sense for a room that I haven’t seen in anybody else.

T: Well, you talk about even greater hospitality in general. In the beginning of the pandemic, cocktails to-go and this is happening, and Julia Momosé is someone that really spearheaded that movement and then allowed it to happen in Chicago. She’s just an incredible professional.

J: Agreed, and I can’t wait to get to Chicago and see her there because she’s been such a force in the industry. And what I love about her is that she’s never been one to beg for the camera. She’s never been on the awards platforms. And yet, the camera has rightfully found her. Press has rightfully found her. She has earned it through steadfast, consummate professionalism. She’s earned all the awards without going after them.

T: Including a VinePair Next Wave award. I have to call that one out because we have awarded her as well. I’ve reached out to her, hoping to have her on the show. We have been speaking about it, but she’s coming soon to the podcast for sure.

J: Absolutely. I love it. She’s great.

T: Jill, final question for you today. If you knew the next cocktail you drank was going to be your last, what would you order or make?

J: I’m a sucker for a good Margarita. That sounds so basic. It’s funny because everybody always asks me what my favorite drink is, and I always say Margaritas, which is why I don’t drink Margaritas. They’re easy to drink if they’re made well. They have awful and amazing results at the same time. Lately, my thing has been lower-ABV drinks. I don’t drink a lot, to be honest. I’ll be honest, I don’t make cocktails at home. It’s one of those things where you get your fill of it at work. My new thing lately has been Montenegro Daiquiris. They’re low-ABV, so it’s a nice alternative. That’s been my jam lately. If it had to be today, that’s probably what I’d go out on.

T: Is that 2-1-1 that you’re shaking up?

J: Yeah. I usually bring it down to an ounce and a half. Because the Montenegro is already sweet, I would go a little heavier on the lime. So I would probably go two and one and three-quarters.

T: Amazing. Jill, thanks for spending some time with us today. It’s been wonderful. It’s been a blast. The Scofflaw is an incredible cocktail, and a wonderful section there at the end.

J: Thanks for having me. This has been really fun. Thank you.

T: Thank you very much.

If you enjoy listening to the show anywhere near as much as we enjoy making it, go ahead and hit subscribe, and please leave a rating or review wherever you get your podcasts — whether that’s Apple, Spotify, or Stitcher. And please tell your friends.

Now, for the credits. “Cocktail College” is recorded and produced in New York City by myself and Keith Beavers, VinePair’s tastings director and all-around podcast guru. Of course, I want to give a huge shoutout to everyone on the VinePair team. Too many awesome people to mention. They know who they are. I want to give some credit here to Danielle Grinberg, art director at VinePair, for designing the awesome show logo. And listen to that music. That’s a Darbi Cicci original. Finally, thank you, listener, for making it this far and for giving this whole thing a purpose. Until next time.

Ed. note: This episode has been edited for length and clarity.