Hitting on 16: An Autobiography of BlackJack Fletcher

Hitting on 16: An Autobiography of BlackJack Fletcher article feature image

The Westgate Las Vegas SuperBook

With an ironclad fist I wake up and
French kiss the morning
While some marching band keeps
Its own beat in my head
While we’re talking
– J.B. Jovi

You should wake up each day, brother, and kiss the hell out of the morning.

Each day on this earth is a good one, no matter what is going on in your life. As I sit in the early morning glow of the Las Vegas sun, I am in a reflective mood. I realize that most of you out there don’t know who I really am or what my story is or how I became part of your lives. And so I will try to elucidate just who BlackJack Fletcher is and how he came to be.

Early Years in Long Island

I grew up on Long Island to two hardworking, blue-collar parents. They scratched and clawed and saved every penny to give me and my three sisters a storybook, peaceful, suburban upbringing. And they succeeded at that. I suppose my grandfather, Vito, was my introduction into gambling. I vividly remember him taking me to the racetrack as a boy. I remember him taking me to Mets games. I remember him sitting over his kitchen table looking at the racing form or the previous night’s box scores. My dad gambled a little here and there, and I distinctly remember him betting on the Buffalo Bills in Super Bowl 25 and being very upset when Scott Norwood missed that ill-fated kick to win the game in Tampa. I didn’t know a lot about gambling at that age, but I knew it made people excited and I knew I loved sports. Little did I know those interests would converge later in life.

Coming Back to New York

My sisters and I were the first in our family to graduate college. I earned my degree from American University in 2006 and truthfully never intended on going back to New York. You know what they say about best laid plans, though. In my senior year of college, my oldest sister, Terry, was diagnosed with cancer. It had spread and the doctors weren’t sure what to do. Ultimately, she had to have surgery and had several organs removed that would drastically change her way of life. I decided to move back to New York and move in with her to help her adjust. I applied and was accepted to Hofstra University for law school.

Thankfully, Terry was stronger than any human I’ve met, and she adapted spectacularly well to her new way of life. I neared graduation at Hofstra in the spring of 2009. The economy was pretty bad at that time. The only thing I found interesting in law school was criminal law. I thought I could do either side of it, so I applied all over the country for jobs as a prosecutor or public defender. I had three options by graduation. I was a good student but never a great one; the 3.0-3.3 GPA range was where I lived. One job was as an Assistant District Attorney in Boston. That possibility excited me, but I would have had to live in the city of Boston, and the pay was just $38,000. The second was as an Assistant District Attorney in Las Vegas. That one was very tempting. VERY tempting. However, as you all know, I like gambling and drinking, and I had the foresight to think that 25-year-old BlackJack might just die out there at that point. The third option was as an Assistant State Attorney in Stuart, Florida, about an hour north of West Palm Beach. It was the highest-paying option and boasted the cheapest cost of living, so I decided to hell with it: Florida-bound I was.

My Time in the Swamp State

I spent eight years in Florida. I didn’t enjoy one of them. Don’t get me wrong: There were good moments — great ones even. But I don’t think I enjoyed the bulk of a year from 2009-17. There were several jobs, including my own practice, none of which I enjoyed. There was a marriage, which came and went for a variety of reasons, among them the depression I felt over having a job I hated and living in a place I detested. Your boy was not in a good place. Depression felt like my only friend.

I tried to change careers several times during that period, but if we are being honest, the attempts were half-assed. I would start up a blog and run it for a few days and send the link to Barstool Sports founder Dave Portnoy back in the day when that was how you got hired at Barstool. Once I even got a “not terrible, keep writing” from him. It was the best day I had in a long time.

The Turning Point: Interning at Barstool

There came a point after my marriage ended, in 2017, when I was living in Miami, that I decided if I was ever going to change things I had to just jump. Sometimes there is no net. Sometimes we don’t know what will happen. Sometimes you just have to take a leap. So I decided to go back to New York and try to figure out what to do with my career. As I was boarding a plane from Miami to New York, my great friend Louis Roberts at Barstool Sports sent out a tweet. He needed a gambling intern. I sat down and started immediately composing an email. The subject line was “The Search is Over,” and I delivered an over-the-top performance to him about why I was his guy. A few days later, Lou responded that he might need me. After several more emails, I was set for a meeting with him and Dan “Big Cat” Katz. I couldn’t tell you many more times in my life I was more excited than that moment.

I decided, having been a Barstool fan for a long time, that if I had the chance to walk through their doors, I was going all out. I wouldn’t be conservative. I wouldn’t be afraid to take chances. I would do what they would have done in that position. So I did. I dressed outrageously. I made bold proclamations. I started talking like a blend of a high school football coach and an ’80s/’90s wrestling promoter. I also started winning. A lot.

I quickly realized that I loved what I was doing and that if I wanted it to stick, I would need to spend a ton of time on my newfound work. Which was, of course, gambling. So I started spending 6-8 hours a day analyzing and breaking down games to make picks. Then the Periscopes started, and everything kind of evolved from there.

The Action Network

One day I spoke with the effervescent Chad Millman at The Action Network. Chad couldn’t have been more sincere or excited about working together. And this isn’t me blowing sunshine up anyone’s ass, but Chad has been the most supportive and encouraging person I could imagine working for. The things on my plate now, I never could’ve imagined a year ago, and I owe that to The Action Network and everyone there. From Chad, to Scott, to Evan, Connor, Gabe, Matty, Paulie, Geoff, Chris, and everyone else, I love these guys.

And now I’m here as your friendly gambler who dresses more like Elvis than someone who holds a license to practice law. Someone who fits much more comfortably in Las Vegas than a courtroom. Someone who lives his life in full view, because I know and remember what it’s like to be on the other side of the computer and crave that access. I guess the biggest message I can hope you take out of reading is this: Don’t give up. Ever. If you’re unhappy in life, go change it. It might be hard, it might really suck for a while, but I promise you — it gets better. If you have a dream, pursue it. Don’t give it up, because you never know what’s around the corner in life. A year ago, nothing was going my way; now, I couldn’t ask for anything more. Don’t quit on yourself. Work for your dreams, and your dreams will work for you.

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