Saint Paulie and prison bells, Part 1
by Ray Ray Smith
You never know when you’ve reached the top of the mountain until you start sliding down.
As the panic of the pandemic faded and Christmas of 2021 approached, I was a 46-year-old securities lawyer in southern Florida, specializing in corporate finance. Life was good. Everybody called me Ray Ray, a childhood nickname I liked. I had black hair with a few silver strands, a wife named Nadine whom I adored, and no kids, which was fine because Nadine’s then-28-year-old son, Zak, lived with us for our first three years, and that experience more than cured any fleeting desires for fatherhood. Our beach house on Hillsboro Key was a dream come true. The Basement Ramblers jammed the first Wednesday of every other month, and I met weekly with a crew of racetrack cronies at Pompano Park.
Two Christmases later, everything was gone.
Hurricane Milton obliterated our house and forced us into a high-rise while we debated whether to rebuild. Pompano Park closed. The Ramblers hadn’t met in months because our drummer was battling Bell’s palsy. But most of all, my world stopped when Nadine — my soulmate — died of a sudden stroke in a Save-A-Lot parking lot after pulling in to buy dressing for a Cobb salad.
My family tree, never large and always fragile, sent a few representatives to the funeral before scattering back to southern Pennsylvania. I lost all appetite for work, retired from practicing law, and sank into a long, gray depression. I thought about joining Nadine on the other side during those dark days. But two unlikely saviors eventually pulled me back.
My phone buzzed. The number wasn’t familiar, but it was local, so I tapped the green button.
“Hello.”
“Is this Ray Ray from Pompano days?”
“Am I talking to Parlay Paulie?”
“Live and in person. Took me all morning to find you; the last name Smith didn’t help. You spend a decade with a mook at a racetrack and never think to get his contact information. But I remembered you worked on the sixth floor of that glass building across the bridge and tracked you down like a TV detective.”
“Glad you cracked the case. How’re you doing? You want to do lunch or something?”
“Good, but no lunch. I got something else you might be interested in.” He paused. “And, sheesh, Ray Ray, the secretary at your old firm, told me about Nadine. I’m so sorry. I only met her that one night you brought her to the track, but she was beautiful — and classy. If I had known, I’d have come to the visitation. Can I bring you a casserole or something?”
“No, no — but thanks, Paulie. I’m doing okay. Taking it one day at a time and all that shit.”
I cleared my throat. “So, what’s on your mind?”
“When Pompano closed and left the nearest harness track somewhere around Mongolia, I missed the days. Just for the hell of it, I joined this racehorse ownership outfit called TheStable and bought 10 per cent of a yearling.”
“I’ve heard of it. So, you shifted from gambling in person to online ownership? Interesting. How was it?”
“Good overall. The guy running it, Anthony MacDonald, he posts videos, he’s a great host, you learn a lot.”
“And your horse?”
“Mediocre. The filly raced a few times at 2, but didn’t show enough for 3, so he sold her. You’ve got to expect misses with yearlings. Ownership’s a different can of worms — just as tough to make money as betting.”
“I’ll Google the site and nose around. You want a partner on a horse?”
“You remember Jerry Tillis, the guy with the unlit cigar and the flowered shirts that hurt your eyes?”
“Sure. Jerry’s great.”
“Well, get this. I ran into Jerry at Costco. We were buying rotisserie chickens, and we got to talking about old times. Guess what? He did TheStable thing too! We all miss the track and the friendships.”
“Absolutely. Those were fun days. They were always more about the people than the bets. I shed tears driving away that last time.”
“Exactly. So, here’s the situation: Jerry’s pulling together a group of at least four to buy a horse. If we get more guys, we change the math. You in?”
“How much?”
“Depends on the horse. Ownership can be fast-food prices or a five-star experience, but it ain’t about the money or the horse. It’s about us. Jerry wants to reunite the old gang. Since we can’t go to the track, the plan is to meet on Tuesdays at nine a.m. in the McDonald’s on Raiser Road. They got a kids’ playroom, but no kids at that hour. We’ll watch videos, learn pedigrees, and maybe one day cheer for a horse we own.”
“Just tell me how much. I’m in. I’ve been in a bit of a rut, so thanks for thinking of me, you’re a real saint.”
“We ain’t got time to waste. The sales season’s almost over. We’ve got to buy soon. So next Tuesday — kids’ room, hot coffee, horses. I suggest you conduct some research on the fractional-ownership site. We’ll make a plan.”
“Book it. I’ll be there.”
Next stop: Prison, yeah, I never saw it coming either.

















