Mastering the art of storytelling to drive change.

ThanksGambling: Memories of a father-son tradition

11 / 25 / 2020

I could see the look of surprise in my father’s eyes as he dipped his hand into the pocket of his Northwestern sweatpants and pulled out a $50 casino chip. 

“Ah, shit. Forgot to cash it.” 

We’d just tossed our luggage into a taxi at the Desert Inn. It was a couple weeks before Thanksgiving, and another great father-son trip to Las Vegas was in the books. At least I thought it was. 

Dad looked at me, his eyes wide again, then jammed the chip into my chest and said, “Go back inside! Play one blackjack hand — do-or-die — then either cash it or run back!” 

We shared a mischievous laugh. Dad ran this “do-or-die” thing at casinos frequently. He’d long ago tired of the marathon gambling sessions that were actually part of Sin City’s attraction for me and my friends. Many years in this town had taught him that “The House” would be taking his money eventually — might as well make it quick. 

I swiped the chip from his grip and scampered back through the front doors of the Desert Inn. In the early 1990s, the D.I. was one of the last vestiges of old-school Vegas, and we’d stayed there a few times before it finally got the wrecking ball in 2000. 

Thirty years earlier, my Dad had been a student at Denver University. After he turned 21, he took the 11-hour drive from D.U. to the D.I. On that trip, he saw Sinatra (my Lord) perform at another legendary Rat Pack haunt —The Sands. My father swears that after the shows, Sinatra would deal blackjack on the main casino floor — and he would give the players the advantage of showing both cards at the start of each hand!  

Three decades later, I’m racing past the bell desk at the D.I. like an Olympic sprinter. I hit the brakes when I get to the edge of the casino floor and start scanning the blackjack stations. I don’t want an empty table — no time for dealer shuffle. And something else tells me I don’t want a full table. 

I settle into a chair two seats away from a lone player. The next hand starts, and I put Dad’s chip on the felt. I draw a king and a queen against dealer’s seven. Stick. He busts. Winner! Time to cash out. 

Or is it? 

No way. Can’t leave on the heels of a hot streak! Yes, I am fully aware that one winning hand is not a streak — much less a trend. But rationalization is a powerful thing. Gotta play one more. 

Dealer flips up a 10 and I have to pull four more cards. Bust. I’m back to $50. 

I couldn’t tell you the cards that were dealt over the next several hands — just that there were several hands. We go back and forth, and eventually, I double my bet to $100 on a truly final exchange. Winner. I’m outta there. 

Unless there’s a line at the cashier’s cage. Goddamnit!   

Those three minutes standing in place, looking down at the hideous D.I. carpeting, felt like an hour. Finally, I get waved down to the end of the long marble counter. I nudge my chips towards the cashier, she counts, then slides back two crisp C-notes. Those bills felt like they were just delivered straight from the Treasury. 

Now I’m Gale Sayers, cutting back left and right to avoid the D.I. strollers. I bolt through the exit door and beeline toward the cab stand. Our car has pulled forward a bit from its original place in line. 

As I open the door, an unmistakable expression on my father’s face tells me that he’s pissed.  

“What happened? We’ve been waiting out here for 20 minutes! What the hell took you so long??”

I didn’t really have a good answer. The truest one would have been: “Dad, I thought you’d get a huge kick out of it if I came back with a couple hundred.”

Instead, I sheepishly told him that the table was feeling hot and I lost track of time. I sounded like a child and I think my stupid answer almost annoyed him more.   

“What the hell is the matter with you? You know we’re waiting here. I said ‘play one hand!’” 

He was shaking his head in disapproval. It was a familiar shake. I’d seen it more than a few times in my youth, and it always hit me right in the heart. My Dad is not a stern man. Quite the opposite. But that look of disappointment could be a dagger. I may have been 25 years old sitting in that cab, but I felt about six.

By now the driver had pulled out of the D.I. circle and we were on our way to McCarran International. It was the end of a wonderful trip, but one that all of a sudden I’d felt like I’d ruined. 

A few minutes of quiet in the car. Then Dad looked at me and said: “So?” 

“So what?” 

“So, what happened?” 

“Oh, I left with $200.” 

I pulled the two crispies out of my front pocket and stretched them out. He took them from me and didn’t say a word. 

A minute later, after I’d turned away to look out my window, he tapped me on the shoulder. I turned back to face him, not sure what to expect. Dad looked at me, separated the two bills, then extended one toward me. He started to smile, and then said: 

“Okay, okay. Good job. Good work.”

At that second, we simultaneously roared into laughter. A best-friend type of laughter — for the nature of our relationship has always been that as much as it’s been father-and-son. For better and for worse.

And of course he liked the fact that I’d quadrupled his stake.  Not that the extra $150 was going to make any difference in his life or mine. But that’s not why bettors bet. At least most of them. 

That Vegas excursion happened more than 25 years ago, but parts of it feel like it was just last week. We’ve taken several more trips since, and except for a couple of group outings on my big birthdays, it’s usually just the two of us. 

On these jaunts, we’ve got the cadence down to a science. Dad bets horses during the day while I’m rolling craps and keeping an eye on our sports bets. We meet later in the afternoon to watch fourth quarter action on the games that still matter. Then dinner at Portofino’s, where we used to take a photo to commemorate the trip.  

Over the last few weeks in the run-up to this Thanksgiving, as we’ve all been coping with the challenges of a 10-month pandemic, a lot of memories with my father have been flooding back to me.

Unsurprisingly, most of these flashbacks are set against a backdrop of betting. I mean, I learned this stuff early. I started staying at my Dad’s house on weekends when I was 13 after he and my mom divorced. The indelible memory I have of that time features seven guys sitting around a big card table, smoking cigars and playing Liar’s Poker, which involves guessing the serial numbers off cash bills pressed to their foreheads. And on went my education from there.  

But through all of the ups and downs in our relationship, the great fun that my Dad and I have had gambling — and talking and joking and laughing about gambling — has in a strange way always connected us.  

Only recently did I learn that this connection also existed between him and his dad. In the 1950s, my grandfather bet with a Jewish bookie named “Potsy” Pearl — who happened to be connected to the Chicago Syndicate. The Mob. And for years, without my knowing it, when I’d been gambling on the golf course with my Dad and his friends, one of them was Potsy’s son-in-law. And he and my Dad would bet each other on anything that moved. 

Looking back on all of these times and learning about how this derelict Golden tradition has been passed down from generation to generation has motivated me to excavate more memories and scavenge more stories.

There’s an authentic camaraderie that springs from the culture-of-the-wager. All bettors know it. Winning and losing has the power to build a bond based alternately upon thrill and empathy. And a ton of laughter.

I’m not saying it was a good example that these fathers set. That would be a hard point to argue. But there’s no question that I am thankful for all of these experiences I’ve had with Dad —  for they’ve brought us closer together. And that’s the win that counts.