It’s Breeder’s Cup weekend, which means it’s time to tell a sad story about an old racetrack pal. So this is the mostly true story about my friend Jimmy One Shoe, whose rags-to-riches-to-rags story probably resonates for anyone whose desiccated soul belongs to those cruel ovals.

Jimmy was the assistant night manager at an oil-change joint — something like Jiffy Oil — when Canterbury Downs came to Shakopee in the mid-80s. He was sharing a room at a vagrant motel on the Minnesota River flats with his friend Skip, who was living off the meager proceeds from a life insurance policy that his dad had taken out shortly before the old man was killed in a tractor mishap. Jimmy and Skip were maintaining at about 125 pounds each, the result of a diet rich in generic macaroni and government cheese. But, that was about to change. In a jiffy.

Jimmy and Skip scraped together a $50 bankroll one Saturday and discovered an enchanted new world at the track. They savored an all-carb feast at the clubhouse buffet for $5 each. The Clubhouse Special was usually something involving mystery meat. Creative names like Cinderella Chicken or Poultry ala Wilson generally masked a meal of instant gravy, instant mashed potatoes and instant dinner rolls. Along with some meat that had apparently fallen off elderly roosters. But Jimmy and Skip were not exactly gourmets, and they were happily sated.

And so they proceeded to bet the chalk until they were down to $5. Their instinct was to split another clubhouse meal, but they thought better of it and bet a horse named something like Skip Town. A hunch bet. This was 30 years ago, so I might be off on a few details.

What I do vividly recall is that the horse was winless in 30 races, and no bargain at 40 to 1. The three best horses got caught in a ferocious speed duel, however, and as they tired Skip Town began to gain ground because he had, as always, avoided fatigue. Skip Town won the race by a nose and Jimmy and Skip cashed for $210.

Skip was something of a sluggard and didn’t think much about it. But Jimmy was smart and not content to spend his life sharing a motel room with a shiftless roommate and a colorful variety of insects. He had found a calling.

Jimmy found some sharpies from out east who seemed to be cashing big time. Too insecure to strike up a conversation them, he instead discreetly followed them around and would scoop up their losing tickets when they tossed them to the ground. By studying those dead tickets, he learned about their betting patterns and the kind of horses they favored. One thing he discerned quickly: they liked early speed and an inside post. That was the prevailing track bias, as Jimmy was quick to understand.

Jimmy One Shoe eventually realized that if he was going to escape squalor, he would need to hit a big Pick Six. He hit a few little ones — making maybe three or four hundred bucks at a time — and saved enough money to bet some big tickets.

Except on weekends, Jimmy couldn’t get to the track until after the start of the Pick Six, so he would send Skip to the track to put in the ticket. Finally, Jimmy had the confidence to bet a big one — a $428 ticket that promised to pay more money than he made in a month.

Jimmy got to the track after the second leg of the Pick Six that day — just in time to learn that Skip had used the wrong horse in the first leg. Jimmy was about to head off to the clubhouse bar to drown his despair, but he studied the ticket first. Skip had used the wrong horse in the first race. And that wrong horse won, paying $28 to win.

Jimmy was in business. It came down to the last race, when he again used just one horse. Well, actually two, because they were part of a coupled entry. One of the two had no chance to win, but Jimmy figured the other one could wire the field. The one Jimmy liked finished third. But the one that figured to finish last woke up and won the race. So Jimmy had actually picked only four winners, but hit the Pick Six. He went home with a check for $72,000 and a heart murmur caused wither by exhilaration or the clubhouse buffet.

It was the luckiest day of Jimmy’s life. Or perhaps the unluckiest. You bet the judge.

The next day, Jimmy deposited the check, evicted Skip, bought a new but inexpensive car, and quit his job. He had turned pro.

Jimmy spent his days betting the horses and his nights studying the Racing Form. This went on for almost 15 years, but the trend was bad. Maybe it was emotional and physical fatigue. Maybe it was the loneliness of life spent in a depressing bubble. Maybe it was the 90 pounds that he put on at the buffet.

One day, he decided to spend his final dollars on one last Pick Six. He hit the first five, and then watched as the single he used in the final leg — a 20 to 1 shot — came from behind to win the race.

The smile was still on his pasty face when the stewards put up the inquiry sign. Jimmy’s horse came down. He headed out the door with $28 to his name, the proceeds from the consolation payout.

Jimmy’s car, now rusted and 150,000 miles older, did not start. Luckily, he still remembered how to change a tire. But, in his anger and shame, Jimmy failed to secure the jack.

I am slightly pleased to report that Jimmy is still at the track, although reduced to the horse player’s ultimate ignominy: life as a $2 show bettor. So if you go out to the track one day and spot a porcine old man with government cheese stuck to his grizzled chin and a wrist clutching a battered cane, say hello to Jimmy One Shoe. Tell him you’re a friend of a compulsive horse player who used to know him. You don’t have to mention my name, but you might tell him that you know how he got his nickname.

I didn’t lose any real money last week. In fact, my picks went 3-0, but I fell behind my one-time protégé (and now sworn enemy) Colton Molesky when he hit a chalky seven-team, money-line parlay that paid $300 and change. I’m not going to chase his money or mine, but I did step it up a bit with my Week 9 mythical wagers.

Tampa Bay at Carolina

Ryan Fitzpatrick, the former and current Tampa quarterback, leads all NFL colleagues in pretty much every category. Top QB rating; 36 passing yards per possession; a whopping 10.7 yards per pass attempt (nobody even close). Fitzpatrick always comes back to Earth, and I can only hope that it doesn’t happen this week. Or that if he does, that the awful Bucs defense helps me out by handing 500 yards of offense to the Panthers.

The pick: Carolina 34, Tampa Bay 30 — Over 55 for $80

Oct 28, 2018; Cincinnati, OH, USA; Tampa Bay Buccaneers quarterback Ryan Fitzpatrick (14) against the Cincinnati Bengals at Paul Brown Stadium. Mandatory Credit: Aaron Doster-USA TODAY Sports

Tennessee at Dallas (Monday)

Dallas has gone under in 13 of its last 17 games; Tennessee under in nine of its last 13 regular season games. The Titans haven’t scored more than 24 points (not counting overtime) in 19 straight games. Mariota is averaging 172 passing yards per game, worse than every quarterback with the exception of Josh Rosen. Dallas ranks 26th in plays per game — 60.4 — because the Cowboys are basically the David Price of football with their penchant for taking the clock down to the final click before every play.

The pick: Dallas 20, Tennessee 10 — Under 40 1/2 for $40

And, finally, a three-team teaser. For those who are not yet degenerates, this bet pays roughly 1.6 to 1. I get a six-point break on each team I select, but the only way I cash is if all three cover that altered number.

My three teams

Kansas City minus 2 1/2 vs Cleveland; Chicago minus 4 vs. Buffalo; and Dallas plus 1/2 point vs. Tennessee. I’m risking $21.50 to make $30. It’s a sucker bet, and my shame group will not be surprised that I hope to lose this wager just to teach myself a lesson.

Continuing the horse theme, listen here Minnesota Line host Sam Ekstrom and I chat about the Breeder’s Cup on this week’s podcast.


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