Alan ‘Dink’ Denkenson Q&A: ‘This is definitely the life I wanted’


Professional sports bettor Alan “Dink” Denkenson was interviewed by VSiN host Gill Alexander in May 2020 at the height of the pandemic shutdown of sports and betting. Dink died Wednesday at the age of 69.

Gill gets Alan to open up about how he got his nickname, his trademark hair, how he got his start in sports betting, his felony conviction on bookmaking charges, the movie based on his life and the current state of the betting industry.

You can listen to the whole interview from Gill’s Beating The Book podcast here. This transcript was edited.

Alexander: I'm thrilled to have this guy on. I haven’t had the opportunity ever to have spoken to him prior to this. He cut his teeth back in the day when he was a kid betting horses in New York, became a bookmaker in New York, New Jersey. It didn't go so well in the end, and he got busted and spent some time in jail.

Came to the dark side after that, the dark side meaning the betting side. Maybe not the dark side, maybe that's a good side. And has been a renowned sports better for many, many years, primarily on a sport of hockey, and has been the subject really of a couple films. One, Bruce Willis playing a character that was based on him in 2012's Lay the Favorite. Then, of course, many of you are familiar with The Best of It from 2016.

Apologize for the long intro. Let me just start here with two perfunctory questions that I did not reflect on very deeply. But one, the last name is Denkenson, the nickname is Dink. Was that just somebody mispronouncing it at some point?

Dink: Yeah. My sixth grade teacher was calling me Dickinson. And then I was caught by a fellow student in my class doing my math homework during class. He came up to the teacher and said, "Dinky is doing his math homework." And somehow the Dinky name has stuck for 55 years since that day.


Alexander: And the other thing is . . . your hair. This is the first thing that people see. Has this always been a signature of yours?

Dink: This is my hair. Yeah, this is what it is. Yeah, I guess that's kind of odd because my dad lost his hair at a pretty young age. So it's been one of those things that I'm known for. It's not my favorite thing to be known for, but it's OK.

Alexander: It's just a signature of yours. It's a very iconic thing for you.

Let's start at the beginning. I mentioned that you grew up betting horses in New York. Where did you grow up specifically, and what was your first experience with the glory that is wagering, sir?

Dink: My first 37 years were spent in various places in Queens. I grew up my first 10 years in Richmond Hill, moved to South Jamaica, which was a co-op on the old South Jamaica race track. At 15, I was playing a lot of basketball and two of the older kids, Steve Rosenblatt and Barry Lieberman, took me to Roosevelt Raceway, and that day changed my life. I loved it there and I fell in love with the action.

I didn't have any money, but I think that helped me because I was pretty regularly going to the tracks since I was 16, without a bankroll, until I got one. And by that time I kind of learned enough about handicapping to be making a profit while I was going to college. Mostly in the night tracks, that was the hottest track in New York. And then I segue to day tracks kind of when that game fizzled.

But I was there on the opening day at the Meadowlands. I think I went to Roosevelt every day for a meet, except two. That was just my life. It was going to school during the day, going to college, not doing any work outside of the classroom, going to classes, playing poker in the cafeteria and then going to Roosevelt Raceway.

Alexander: Sounds like a lovely childhood to me. Were horses the only thing you bet or was that just your favorite thing to bet?

Dink: It was when I cut my teeth in it when I was 17. The beginning of my gambling career was all horses. I met a man at the track who was a small bookmaker and he told me to gather up my friends and have them bet with him and he'd give me 25% of the losses back, or the quarter sheet. After two years of doing OK, I realized maybe I should do this myself and get 100% of the losses.

I was booking for a little while, back when I still lived with my parents in Forest Hills.

Alexander: Eventually, you got busted. But I would imagine you got big enough. Well, maybe it didn't have anything to do with you being a big enough bookmaker. Maybe it had to do with a specific client. How did you ultimately run afoul of the law with that?

Dink: I grew. I started booking what would be considered squares. Then I gradually got a sheet of wiseguys. I booked the koshers. I booked the computers. I booked Mickey Appleman. I booked Alan Boston in his formative years. And that turned me into a broke bookmaker because I wasn't able to handle wiseguys for a while. I had to borrow some money, regrouped, learned how to be a good bookmaker and grew.

My strategy was: Never turn down a customer who paid. It was hard for a while because I had eight wiseguys and I never got buybacks in those games at that time. I have to think about what year that was now, about 1977. Those games started winning extremely regularly, so that put me in a hole.

I got out of the hole. I turned my business around. I ended up having 150 customers who bet regularly. There was always two-way action. I opened at 4 o'clock Eastern and my first two customers were Mickey Appleman and Alan Boston, and they would fire the whole college basketball board a lot of times against each other with the same number. I innovated. I didn't want to book that high. I wasn't the biggest bookmaker in the world, but I took NBA totals, which weren't very popular back then. And there was a lot of two-way business from middler's versus sharps. And that helped me as well to get a bankroll. An agent would give me a customer and I got one from Detroit — no idea who he was — only talked to him one or two times as a person. He was just a name and a bettor who I guess I could see that he was betting the sharp sides late. So I guess he was laying off his business, which I never cared to discuss. He was just a customer and he was betting the right sides very late. So he really didn't have an advantage, betting bad numbers. It turned out he was involved with Isiah Thomas and running a dice game.

Dink: The FBI was aware of him and they tapped his phones and I was one of his bookmakers and they assumed I worked for him as opposed to just having a customer-bookmaker relationship with him. Got arrested, took four years for the case to get prosecuted. I hired a very good sentencing lawyer, Alan Ellis. And he probably saved me from going to a real jail and so I got into a work release jail. I worked at a friend's deli for 300 days straight. Worked every day so I was never really in jail during the daytime. It was kind of sleepover jail.

It wasn't that bad. I drove my car to jail and I drove my car to work. And then I drove my car back to jail. I took an extra hour or two to go to a GA meeting.

That got me a felony. And then I decided I can't do this anymore because the second felony might mean some serious jail time. So I had thought I had learned enough from the people who bet with me to be a successful bettor. And just like my bookmaking career, I learned the hard way that that's not that easy. And I had to regroup there, too.

I had a decent bankroll, which got cut into, because I bet too high for my talents. But then again, I learned to take that into consideration. Work harder, still was always a good hockey handicapper, but I was trying a little too hard to win at baseball. Regrouped, build up my bankroll again. And now I've been doing that since 1995 when I moved to Vegas, so 25 years on the other side. So about 15 years bookmaking, 25 years betting.

Alexander: The big takeaway, obviously, it that it's a roller-coaster ride for you. But afoul of the law aside, if we could just put that to the side and table that for a second. You could not have gotten, it would seem, a better education to become a successful sports bettor than from your entire trajectory. To book sharps, to see, oh, this is how I'm getting beaten to book squares. And then to really realize as a bettor, then the experience again, as a bettor early on, as you said to have a lack of success early on. But the book making lessons must have helped you tremendously on the other side.

Dink: Yeah, sure. It was very easy to see what not to do. Because I had a ton of squares and the squares tended to lose regularly. The wise guys always beat the closing line. I think most of my time is now beating the closing line as opposed to picking winners.

Alexander: Was that the single biggest lesson Dink? Was it beating the closing line? I mean if someone is landing on this… If someone's landing on this show for the first time, let's say they're a novice bettor. What would be another bit of macro advice you would give them as like the single biggest?

Dink: There's so much more to learn than what you think you know. That you have to… It's great if you could follow somebody or know somebody who's sharp and see how much work they do, because I don't know any successful gamblers and it's harder now, because you have to program and have bots and you know, really have some kind of a model, whether it's a model that you can push into a computer or a model, you can write down on paper, I'm still a paper and pen guy.

But to arrive at a line that will get you the bettor, that will beat the closing number. That's my objective in beating the closing number. If you are just going to bet without caring what number you're laying and when you're laying it at the right time, either early or very late, you're up against a lot of very sharp people now. It's really hard. I would stress that there are brilliant people in this business. When I first got into betting and bookmaking, a college degree would make you one of the top 5% of the people who were in the gambling field. And now a college degree would probably make you in the bottom… Just a college degree would make you in the bottom 10%.

Alexander: I mentioned all the things that Alan has done betting-wise. I didn't mention that a couple years ago, in the World Series of Poker super senior event, you cashed in that. And If we talk wrestling, you'd stay here for two hours. Are you still obsessed with wrestling Alan?

Dink: Wrestling's gotten me by [during the sports break for COVID]. I listen to some podcasts every day.

Wrestling is a nice little fantasy world that's created to get you through the hard times of the real world.

Alexander: As someone who is 66 years old Dink, and you look at some of these young [sports bettors] who are super educated and super smart. Do you look at guys like [Rufus Peabody], just to hold him up as one of many, who do that? Not a huge universe, but more than just him, obviously. Do you look at them and have an almost… Is it admiration? Is it jealousy? Equal parts that, what is it for you?

Dink: It's 90% admiration. I think it's a little jealousy that I can't be like them. I can't do what they do. I can't code. I barely can use Excel. I'm doing things the primitive way. I've become the dinosaur of the business, but I'm friendly with all of those people.

Rufus, I know. I wouldn't consider him a friend, but I definitely respect him. I think he respects me. I'm friendly with Joey Tunes. I'm friendly with Spanky. I don't want to miss people. I'm friends with Rob Pizzola. A lot of people who do a lot of coding and great work.

And they respect me because I paved the way for them, I guess. And they know I respect them. I don't consider them enemies. They make me do work a little bit differently to get the good numbers. I have to bet before them, because I have to bet when the market doesn't have that much volatility. I have to bet when Pinnacle and CRIS open right away, because they don't want to touch those lines because they don't get down enough. That really helps me. But I admire them so much. I know them. I know their families, a lot of them. They're just really good people. The ones that I do know, and I consider a lot of them friends and I certainly respect what they do.

Alexander: Is that much more difficult now than it was 10 years ago, 15 years, 20 years. Is it to the extent that it almost deflates you sometimes? Or do you still think that you can turn a profit here consistently?

Dink: I think I can turn a profit here consistently. But I used to be sure I could turn a profit here consistently. I have to keep up on my game, find little things. I've been fortunate. I cashed in the NHC this year, that I was a little bonus, the horse Handicapping Contest. I'm kind of a Jack of all trades, master of none, but trying to beat the closing line is what I can do. And by calling around and by shopping well and having little outs and having people help me a little, get down on good numbers. That's my test, leading the closing line. It's not perfect. I know that's what a lot of gamblers think is the end all to end all. I think it's almost the end all to end all, but there's a time also to know enough about sports to buy back at the right time as well. I always learn. I like to learn, so I like to talk to these kids who do well, and a lot of them have been nice enough to share.

Alexander: So what are you betting these days? So in other words, hockey became the sport that you were best known for. You still play the horses. But you're primarily a hockey and baseball guy.

Dink: Yeah, that's what I want to do. Chasing numbers or something looking for value in the markets on basketball or football. I do that as an aside. Again, if there's a rogue number and I see it moving away from that number, I might grab it at whatever sports book account I have. My edge is much smaller than it used to be 20 years ago. My biggest edge was before Don Best. Don Best kind of ruined the business because it gave you too much information. Instead of working hard to get a line and to see where lines are moving, all you have to do is have a machine that everybody else has. And if you didn't have that machine and that information you were way behind the game. I blame Don Best for making this business highly competitive with people who don't work that hard, because they see the same numbers that I do.

I was there when Caesar's Palace had seven [runners] and Bally's had five at the same time. And I had runners in both places. Laying the five or taking the seven, or both. Times have changed.

Alexander: Some of us hear stories like that Dink and we're just like, "Wow." What an interesting time that must have been.

Dink: That was my biggest regret, that I didn't take advantage of great opportunities. I just thought they'd be there forever. So I've just made a decent amount of money instead of optimizing my gain.

Alexander: For lack of a better way of phrasing this, in a more delicate way I guess. What else sort of pisses you off about the industry? In other words, Twitter's an interesting place, right? No one ever loses a bet there. With legalization has come a proliferation of sports betting media, this network included. What bothers you about this latest evolution? Have your worst fears come true with that?

Dink: No.

Alexander: In some ways?

Dink: Touts bother me the most, the people who have no opinions and act like they do. I'm not quite as obsessive about it as some people. People look at people like Vegas Dave as a prominent gambler, and it's like, "Oh God, that guy’s trying to scam money." It's all smoke and mirrors, and that's not what gamblers should be with that. So I think I'm grouped into that … The people with the highest regard from the public are not deserving of the highest regard. It's people like you who know some of the people because they're your guests, deserve to be respected, and sometimes that respect goes to the people who are just trying to steal your money.

That's my biggest problem with the industry. It's very capable to attract scammers and have the scammers be successful. Also people who take shots and don't pay, credit is a double edge sword. It's good for people who get credit and bookmakers who pay, and gamblers who pay, but it's really a problem when there are lay downs and the bookmakers who have no intention of paying. There was a bookmaker the day before the draft who must have saw what his liability was, and every bet was one-sided, and he decided to close down and come back when a sport would come and not honor any bets that were pending. So in order to get out of that one day disaster that he knew was coming, he just canceled all the bets. You hear a lot of bookmakers are struggling now, so I worry about that too. I only bet with the ones where I know I'm going to get paid.

Alexander: One of the reasons that I really am attracted to all the stuff that you put out on Twitter, and just in meeting you here today is, you're super honest, you're transparent, you're not one of these people who's talking about, "Hey, I win just like I used to." So I always respect honesty. Honesty is not, how can I put this? An abundant quality in this industry, as you very well know far better than I do. So I appreciate that sir.

2012, Lay the Favorite, Bruce Willis plays a character based on you. You were a consultant for this film I believe.

Dink: Well, the girl who wrote the book [Beth Raymer] worked for me and we're still friends. I got to meet the director and the screenplay writer, Stephen Frears and D.V. DeVincentis. Before they did the screenplay they came to look at my office and how I did my business, and we became friendly. And they asked me to be a consultant about all the gambling stuff. So we did 10 days in Vegas, and the first seven days in New Orleans, and that was my half of the movie where I consulted. I was promised a paycheck, I never got it. 

Yeah, 50 Cent was actually a producer of Lay the Favorite if you look at the credits.

Alexander: Wow.

Dink: He was a money backer. He put in money. They sold the movie before the movie was shot, so they didn't want to put anything into the movie, which is why the movie wasn't that good because it was already purchased.

The book is great.

Alexander: Book is better?

Dink: Oh God, the book is so much better than the movie. The movie was canned and the book was very respected. She wrote such a good book that it became a movie. I don't know if you've read the book, but I always advise people to read the book before they see the movie, because if they see the movie they'd have no interest in reading the book.

Alexander: How about The Best of It [documentary]?

Dink: I knew Scott Pearson Eberly, he was a producer at TVG. He was going to do a movie based on The Shrink [Ken 'The Shrink' Weitzner], but in the middle of that movie The Shrink passed away, so he picked it up with Alan Boston and I, and Len Banker, and did a documentary on four gamblers even though one had already been deceased. That was fun, that was easy. We just came to my house and shot a lot of footage. We're still friends too, I talk to him every once in a while. He's in Minnesota now.

Alexander: Yeah. I mean, I guess, when you look back on all this, not to say that you don't have still a bright future, this is not in any way a eulogy of any kind, but when you look back on life, those who are listening to this show who are super fascinated by gambling, by the characters who have created the industry into what it is, had a big hand in it becoming what it is today, and they look at it, I mean, look, we just talked about you. You were a bettor, you became a bookmaker, you went to jail, then you became bettor again, you became a successful bettor, you had movies based on you. When you look back on it all, we all have a story, I know I tell about my mom, one of her sons is a doctor, my brother, the other one does something else. She doesn't know really how to describe what it is that I do other than, "I think he's on the radio." So we all have a lot of that in common. I'm not sure if your mom told everybody.

Dink: My mom told everybody for years that I was an accountant. I was an accountant for 30 years.

Alexander: Does she get what you do now or did she get it finally?

Dink: She's gone now. She dealt with what I did when I went to jail, but until then I was an accountant. She thought she could get me out of going to jail because she voted for somebody who's a District Attorney or something in New York. She never really grasped how the whole thing works. She thought gambling was terrible. She wanted me to be a stock broker and I tried to explain that that's like a cop, and that's not really the most honorable profession. But I've just been lucky. Two years ago for two months, Joanne Wood lived with me. That was another one of those miracle connection things. She's going to be fighting for the UFC Championship against Valentina Shevchenko when Valentina recovers from her injury. I know Shayna Baszler well. She's one of my closer friends and she's going to be fighting for the WWE Championship again. So little things just fall into my lap and they're all a bunch of fun miracles that made my life very exciting.

Alexander: You're thinking of writing a book now?

Dink: I'm thinking of writing a book. I just know my vocabulary. I know how good Beth was as a writer, and I'm so pale behind her that. I write a chapter and I go, "God, this is terrible." And then I send it to her and she makes suggestions and I go, "You may as well write the book for me because that's what it's going to be." She just corrects all my flaws and my lack of a good vocabulary and lack of setting a scene. That's one of my strengths, is I know my weaknesses. Somebody once described that as my strength, that I know my limitations, which is very important in gambling.

Alexander: It's very important in gambling. It's very important in life. It's a universal truism. Recognizing what you don't know is really a function of intelligence. So I guess we answered the question, maybe we didn't, but what I was going to get to was, as you look back on all of it, would you have had it any other way? I'm sure you wouldn't have wanted to go to jail, but you said it was an OK experience under the context of what going to jail means. I'm sure there are little regrets, but just from a big standpoint, a macro standpoint, would you have done anything differently or is this the life that you wanted to live?

Dink: This is definitely the life I wanted. I hate the fact that I'm this old and people are going over my life like I won't have more life coming. But yeah, this is the life that I like. It's been taken away from me by a pandemic. I thought I had five good years left before I couldn't do things because of age limitations. I'm worried about that. They're taking away 25% of my last good years with the pandemic.

Alexander: Think about 28 year olds and 29 year olds or of that age, I've been saying that about that age group, which is, wow, that's prime years. Obviously, they'll have years to make up for it, but it really is time from their prime that you can't get back in some way. So it sucks all the way around, right?

Dink: Also, that it's changed the world. The world's going to be a lot different when we get through it, things that you can't do, things you won't do, things that won't be there.

Alexander: What's the charity you're involved with?

Dink: So Cal Thoroughbred Rescue. They take horses from the racetrack and re-hone them and give them a job to do. It's a small one. Old Friends is a very big one. It's a little Old Friends for horses that aren't all that successful. is the website. If you have a little extra money and you care about horse racing, it'd be great if you'd donate. I will be back when sports reopen giving out picks for donations. It goes right to the charity.It's my giving back. Gamblers don't really take anything, but they don't give back either, so that's my way of giving back. I think a lot of gamblers are now giving back more seeing the way the world is today.