Why I Lost Fantasy Football: A Composition of Failure & Redemption in Eight Parts

Part I: 1989

At eight years old, my Dad encouraged me to stick with baseball. “It won’t be like in Texas,” he assured.

Texas, you see, was shorthand for where my 6-year-old baseball dreams had gone to die. We were outside Houston at the time. I was a dedicated Astros fan whose little league team was, not-so-coincidentally, called the Astros. As a 6-year-old, I thought it was totally normal to be banished to right field.

And you know what that means: I was the best-damn grass fondler suburban Houston had ever seen. No one (including my Dad-coach) remembers me doing much of anything besides picking flowers.

But a couple years later, in 1989, we were stationed in a remote airbase in northern England — about 45 miles south of the Scottish border. The 80s were prime for Baseball Fever in America; but in England: no one could care less. Now a tall-ish 8-year-old, I signed up and was cast as pitcher. (“Cast?” I don’t even know the word it. I’m comfortable using a theatre term here because I’ve gotten a lot gayer since the late 80s.)

Anyways, I was so butch. I had a golden arm. And in the land that baseball forgot, I was on top of the world. I became a champion.

Baseball was it. Baseball was my life.

Part II: 1992–94

Then I got fat. We moved to Guam: a land where 250 days a year were above 85 degrees. This made me a home-sitter. I found potato chips and was living my best 11-year-old life.

My Dad, singing the praises of my eight-year-old glory, convinced (but was it convincing? Maybe: threatened) me to stay with baseball. I’ll spare y’all the drama. But it was a shitshow. I made it to first base once. I got a new nickname that I won’t share with you. And it’s fine to say: my baseball career was over.

When we finally made it to Colorado, the MLB was embroiled in a strike. So I left baseball completely. I packed all my Topps cards in a box and set about looking for another sport.

Part III: Flashback, 1993

My family’s from a small town in the Upper Peninsula of Michigan — the best (and MOST) kept secret part of the state. When people from Michigan talk about where they’re from, they stick out their hand, palm out, and point to a spot. The lower peninsula looks like a mitt.

I always have to add a top hand to remind people that there’s a whole ‘nother section they’re forgetting about.

Being peninsular people — isolated, rural and cold — we split our allegiances. Attached to Wisconsin by actual land, many of us naturally root for the Packers. Our affiliation with downstate folks is tenuous. We call lower-peninsula people “trolls.” (Our only physical connection to them is theoretical: the Mackinac Bridge is the longest suspension bridge in the western hemisphere.) They are trolls because they live under…the bridge.

We’re two hours from Green Bay and six from Detroit. I always thought folks were fans of convenience more than of merit.

As a 12-year-old — already with a strong diplomatic streak — coming into football in a family foresworn to sides, I didn’t want to choose.

Fresh from baseball, and looking for a team, I found one tucked away in the NFC North. A recent expansion team, the Tampa Bay Buccaneers were unoffensive in everyway. Terrible in everyway (probably because they were forced to play half their games in the steaming tundra of the upper Midwest)!

But no one in my family had much to say about them. Had I chosen the Bears or the Vikings, I would’ve been disowned. So I chose the Buccs. It created a sense of tension in the family, but it garnered more pity than ire.

The whole thing ended up being pretty extortive. My Dad and Grandfather, key representatives of each wing of the family-football collectives (the Pack and Lions, respectively), seemed to think it was fine to gaslight a 12-year-old into betting (and losing) $10 — that’s $22 in today’s money — a pop. And because members in each NFL division play each other twice a year, for several years I lost $40 of my hard-earned allowance every season…to grown-ass men who should’ve known better.

Part IV: 2003

A senior in college, I sat with a buddy in a frigid St. Louis bar. The only member of my speech and debate team (I’d long given up active participation in sports) who would watch the game with me was a wicked-smart economist who had a love for Southern things. I offered to buy a bucket of beer and he gladly accepted. We watched my Buccs (who my family had chided and derided for a decade) sail to victory.

The truly amazing thing wasn’t their margin of victory (they beat the Raiders in the seventh-largest differential in Super-Bowl history), but that my entire family had sided with the Buccaneers that year…because of me. After ten years of dogged commitment, WE won.

More people called me after that Super Bowl win than called me after my wedding. Perhaps they understood football…more than they understood me marrying a dude.

Part V: Later 2003

I left football pretty quickly after that.

My family never liked a quitter. But I decided…“Quit while you’re ahead” was a better life philosophy than “Hang onto the glory days.” The Buccs had won; what more did I need?

So I moved to New York; and for a city with two football teams, I was surprised to find out that absolutely no one gave a shit about football. After I came out, the gays reminded me that I should be more interested in Broad-way than broad…shoulder pads.

I stopped caring entirely until, well, my grandfather got sick.

Part VI: 2015

I made a stupid bet, okay? I have this tradition of placing poorly conceived sports bets when I’m in Vegas. My uncle bets $100 on the Packers every year. And a couple of times he’s come out with bank. I thought it sounded fun. I couldn’t bet on the Buccaneers anymore. That was silly. And after years of losing money to my nearest and dearest, it seemed right to start giving money to a casino.

To be honest: there’s something so totally satisfying about telling people you just dropped $20 on the Lions to win the Super Bowl.

“Oh honey,” they’d say (though no one said this. Because straight men who watch football don’t say “oh honey” to other men who do stupid things).

Well, honey, in 2015 they made the playoffs. My $20 was going to turn into thousands! I watched that NFC wild card game that year and remember standing the entire time. The Lions’ lost in overtime — and I just started screaming uncontrollably at the TV.

I guess that’s when I started realizing I was in for [20,000] pennies and in for a pound with the team. But I was cautious. It’s true what people say: “Youc an root for the Lions; but you can never trust them.”

My grandfather was the only real and persistent Lions fan in the family. He took a turn for the worst that year. And when he died in 2016, his Lions gear — mugs, sweatshirts — looked different. As if, infused with something close to solemnity, they were calling out for someone to see his team through.

The Lions had, at that point, a 25-year drought without a win in the playoffs.

But I know how to root for a losing team: you point at the naysayers and shout “I told you! Faith is the only true value in sports.”

Part VII: 2023

“Yeah, okay. Sure,” I said.

Starting a new life, a new career: I wanted to fit in. So I said “yes” to something I had no business saying “yes” to. I was last to draw in my company’s fantasy league (16th in a “random” selection); and I fixed martinis for the draft party. It didn’t even cross my mind that a ‘tini wasn’t the typical draft cocktail.

After twenty years without football, I’d forgotten everything about “football culture” — it had been a bucket of beers that had lured my friend into watching with me back in 2003.

16th; with a martini in hand…I drafted a dream team:

· Two members of my team were from the Buccs. 2023 was the 20th anniversary of their big win, after all. And 1993 made it 30 years of a Buccs-charmed life.

· I drafted a member of the Pack because I thought to myself: if I know everything there is to know about Jayden Reed, I’ll be able to drop his stats into conversations with my cousins, my Dad, my Gram.

· And I drafted three players from the Lions. Jared Goff. Jamhyr Gibbs. Sam LaPorta. A bunch of goofy-smiling, ESPN-approved guys who would, throughout this season, become something close to family.

When I picked my team, I guess I chose a bunch of guys who represented something nostalgic — people who, because of my own sports origin story — spanned thirty years of sentiment.

I lost Fantasy because I’d unwittingly chosen with my heart — a vodka-soaked heart.

I selected a team that represented thirty years of whim; a team that followed the logic of a 12-year-old trying to avoid the pressures of having to choose between his Gramps and his Gram.

Part VIII: 2024

In 1989, I’d pitched a near perfect game. Struggling with the responsibility of celebrity, I was sure I’d play forever.

In 1991, I saw the all-star Roger Clemens play at Fenway (before his, ya know, drugs-stuff). My tenth birthday was the happiest I’d ever been. I swore I’d never care about anything as much as I did America’s pastime.

In 1994, internalizing the Bush-era rhetoric of anti-labor, I started calling the striking baseball players “lazy” and “greedy.”

In 1995, now a football fan, I started my first football pool, illegally hustling $10 bets from my Dad’s friends and my friends from freshman English, to pass the time. (I never won.)

In 1997 Trent Dilfer started revving up a Buccaneers offense that hadn’t seen a chance in hell for quite a while. Their first playoff victory in 18 years was…against the Lions.

In 2003, I was full-throttle, chomping my way to Tampa Bay’s ultimate victory.

In 2015, I watched, demoralized, as my new team (adopted because of a Vegas bet; adopted because of my grandfather’s illness) lost to Dallas.

Then. In 2023, I sat, gloomy-eyed as my Fantasy Football team — not a bad team, really — underperformed in a playoff system that makes no sense.

Wanna know a secret, though? I never felt like my team was bad.

It wasn’t, really.

As it turns out: It represented the best of me and my history.

When the league was finished; after I’d lost; Goff, Gibbs and LaPorta still pulled out their first post-season victory in 30 years. When it happened, I was sitting with my Gram, in her apartment in northeast Georgia. She’d long given up the Michigan winters; and I’d decided to trek down there for a weekend visit.

She’d rooted for the Packers earlier that night. And she rooted for the Lions with me later.

The Lions did what they always do: disappoint. But when they miraculously pulled out a 24–23 victory over the Rams? I cried.

She looked at me and said “Gary would have loved this.”

Gary, of course, was my Lions-loving grandfather who’d stayed loyal to his team his whole life.

We all seemed to celebrate for him — with him. I’d heard that my uncle — the one who bets on the Pack every year? — grabbed a beer and headed up to my grampa’s grave, sipping his brew with the memory of my grandfather.

I poured a drink for myself that night from my Gram’s liquor cabinet. I’d found a virtually untouched bottle of something called “La Grande Passion:” a short-lived liqueur produced by the makers of Grande Marnier.

The kicker? (Football pun!) The liqueur had been discontinued…in the early 1990s. The last time the Lions won a playoff game was the last time this French company had produced a this sweet-and-delicious aperitif.

My thirty-year journey had come full circle…with a glass of some thirty-year-old Armagnac.

The thing about my family is that, though we have mixed allegiances — and though we sometimes delight in extorting money from 12-year-olds — we will always sit down with you afterwards, crack a beer, and commiserate about our collective losses.

My family congregated around the Buccaneers in 2003. And they’ve congregated around the Lions in 2024.

I lost this competition because I tied my wagon to the fate of the unpredictable organizations of my past. And even though I lost, I’ve won back a great deal of memory I thought I’d lost.