Let’s dive right in. For those who may not know my background, I was born and raised in Newton, Massachusetts. I spent my first 18 years there before heading to the University of Wisconsin. While my family isn’t originally from the Boston area, I have family scattered across the US, including in Chicago. Growing up, I naturally rooted for Boston sports teams – it’s how my dislike for the Green Bay Packers began after the 1996 Super Bowl. Annual visits to family in Chicago also meant I developed a soft spot for Chicago teams, considering them my second favorites (perhaps a bit of a bandwagon move, but it was true). I was captivated by Michael Jordan; my uncle had season tickets throughout the entire 90s and, through his real estate work downtown, became acquainted with Phil Jackson. This connection only amplified my childhood fascination with Chicago and the coolness of those connections. Even when I went to college, my Boston team allegiance remained, but in 2007, post-graduation, I moved to Chicago and genuinely fell in love with the city. I wasn’t exactly the coolest kid in my younger years, but in college and especially in Chicago, I found my people and a sense of belonging. Getting my first apartment in Lakeview at 22 was a game-changer. I lived in Wrigleyville (highly recommended if you’re looking to catch 20+ Cubs games a year, like I did back in 2009), Lincoln Park, and the Gold Coast during that period. Chicago became home. Those initial years in Chicago in my early twenties were the happiest I’d ever been, and I knew, no matter where life took me, I wanted Chicago to be my forever home, the place to raise a family.
Fast forward a few years, and like many in my position, I started questioning my career path. Many reading this can likely relate to that feeling of wondering if your current job is your long-term calling. During lunch breaks, I’d find myself online, listening to local Chicago radio, thinking I could do something similar. It was around this time that Barstool came onto my radar. How? Well, as many know, I enjoy gambling – quite a bit. My lunch breaks often doubled as trips to the Western Union by Chicago and Orleans to wire cash to the Bahamas to fund my sportsbook.com account. My Avalon’s (RIP) center console was overflowing with those transfer receipts. I don’t think I ever actually withdrew from that account, just kept feeding it under a fake Bahamian name, much to the Western Union employees’ justified disapproval. Anyone with a history in online gambling remembers this era and probably also remembers Covers.com. Covers.com was a gambling forum where people shared their daily picks and discussed games. You’d find a hot handicapper and ride their picks until they cooled off. On a side note, if anyone remembers the guy who color-coded his picks based on team colors – I can’t recall his name, but that guy was on fire, and I religiously followed his selections. I bring up Covers because that’s where I first encountered Dave Portnoy and Barstool Sports. He posted his “mortal locks” for an NFL Sunday, I tailed them (they lost, naturally), and from there, I started reading Barstool. I was instantly drawn in by the funny videos, the irreverent humor, the random funny moments in sports, and the general internet absurdity. Aside from Collegehumor.com, no other website was consistently putting out that kind of daily funny content.
So, that sets the scene. I was living in Chicago, incredibly happy, but wondering if there was something more for me professionally. That’s when I started blogging. When I began, I noticed Dave covered Boston, Kevin and Keith handled New York, but Chicago was open territory. So, I threw myself into Chicago sports. I fully embraced those teams, deepened my knowledge of their history (which I already knew a fair bit of from my uncle), and started passionately rooting for all of them. As I did, my Boston sports fandom began to wane. To fully commit to Chicago, I felt I needed to completely shut off any lingering Boston allegiance. Perhaps the worst trade of all time: swapping rooting for Tom Brady for the Chicago Bears. Dave initially offered me a job in 2010, but the timing wasn’t right personally. It felt too risky, and I doubted my abilities at that stage. So, for the next two years, I continued blogging, honing my skills and getting better.
In 2012, Dave announced the launch of Barstool Chicago with a guy named Neil – shout out to Neil, genuinely a great guy. Neil, like me, lived in Chicago but wasn’t originally from there, and he faced immediate criticism for it. He never really got a fair chance, which was incredibly unfortunate because he was genuinely trying to do his best. I took on a part-time blogging role for Barstool, and when things didn’t work out for Neil, Dave offered me the full-time Chicago position again. Dave knew my background, and we discussed the best approach for my launch. We agreed the best strategy was to not mention my childhood or previous Boston fandom and to just go all-in on Chicago – covering their teams, city happenings, and blogging about everything internet-related.
Looking back, this decision is my biggest regret, one that weighed on me for years. Why didn’t I just explain my background from the start? I believe my talent would have shone through regardless of where I grew up. But, at the time, the perceived best move for Barstool was for me to dedicate myself 100% to the job and work tirelessly to make Barstool Chicago succeed. And that’s precisely what I did. Anyone who knew me 13 years ago knows how hard I worked. I became obsessed with Chicago sports, obsessed with blogging, obsessed with my job, and I worked incredibly hard at it. I also knew I couldn’t hold onto any old allegiances because that would be even more unfair to the audience. I went cold turkey on rooting for any Boston teams. Super Bowls became meaningless to me; I essentially shut off that entire part of my life and wholeheartedly rooted for all things Chicago, even as they consistently underperformed.
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As the years passed, Barstool’s growth continued, I kept working, and my past became a sensitive topic I actively avoided. I suppressed it from my mind and content because I wanted people to know that my passion for what I talked and blogged about was genuine, which it was. I genuinely cared when the Bears lost to Aaron Rodgers, when Derrick Rose struggled with injuries, or when the Cubs started building something special. The double doink playoff loss absolutely crushed me because it was all I was invested in. Covering Chicago was my job, and I took it incredibly seriously. I went all in and never looked back. When people online would bring up my past, I would DM them to stop, fearing it would ruin my career. Looking back, that’s so foolish. I feel a lot of shame for avoiding it at all costs. It was a minor issue I blew out of proportion in my head. And I know, ultimately, it’s not like I was hiding something horrific; it was just switching teams. Some might care, but most would still appreciate the content and the fact that I proudly represented the city I had come to deeply love and the teams I had fully embraced.
Why I acted this way, I still can’t fully explain, except to say it was driven by fear and irrationality. In my mind, as long as I gave my all and rooted as hard as possible for Chicago teams, it wouldn’t matter. I also never imagined Barstool would become as big as it is, that I would have millions of followers and host a major sports podcast. It started as making jokes online and evolved into something much larger. Barstool isn’t just a job; it’s a life, and that’s how I approached it. My life is my job and vice versa. I pushed myself to work harder than anyone, aiming to take this company to the moon. But hiding my past was the wrong approach. I recognize that now. As I said, it snowballed, and as the company grew beyond just Dave, Kevin, Keith, and me, and we brought on more employees, I became someone people depended on. The pressure mounted each year to maintain my work and continue growing the brand.
So, here we are today, and I’m trying to move forward. I messed up (in the words of Jim Calhoun). I shouldn’t have been ashamed, and I shouldn’t have hidden my past. People will call me a phony and a fraud, and I expect to take some heat for it. But I want people to know that my care is genuine, and I have genuinely cared about Chicago sports, Barstool, and this city for the majority of my adult life. I’ve watched almost every Bears, Cubs, Bulls, and Blackhawks game (perhaps less recently) for the last 13+ years. These are the only teams I root for now, and that hasn’t changed since joining Barstool.
I anticipate some people will hate me for this, which is tough because I’m sensitive to internet opinions and let them affect me too much.
But ultimately, I know many people have my back, and my decade-plus of blogging and podcasting about everything, including Chicago sports, speaks for itself. And I appreciate everyone who continues to support me. Throughout this, it’s been incredible to realize the support system I have. The 70+ people in the Chicago office have my back, and they know that deep down, I’m a good person trying to do my best for everyone. Despite my regrets, I need to focus on the positives. I’ve built an incredible office where I actively try to give people opportunities and the kind of life I have. I believe I’ve achieved a lot in that regard, and that feels amazing.
And honestly, this has probably been the worst I’ve felt in my 13+ years at Barstool Sports. I hate the feeling of letting people down, and that’s how I feel right now. Side note – if you’re looking for a diet, extreme stress, self-criticism, feeling awful, and losing appetite is surprisingly effective. For the first time in my life, I might be on track for a six-pack (my personal six-pack goal is being able to see my own penis, grading on a curve here).
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I’ve rambled on for too long and clearly lost my blogging stamina from the days of 10 blogs a day. I’ll leave you with a quote from another transplant who became synonymous with this great city: “The past is for cowards and losers” – Mike Ditka. Actually, let me revise that: “The past is for cowards and losers, but if you bring up mine, I’ll no longer run from it or feel ashamed. Bear Down.” – Big Cat.
