After years of infield pranks, is he Churchill Downs' most wanted man?

2022-05-14 18:18:00 By : Mr. Felix Guo

An old photo shows Skip Anderson dressed in oversized overalls and a large raincoat on Kentucky Derby Day in 1977. 

It was certainly an odd get-up for a cloudy day with minimal chance of rain, but there was so much more to that specific wardrobe choice than a little eccentricity. 

Anderson had a whole volleyball court beneath his clothes. 

About two months ago, Anderson invited me to look through his photographs, notes and ledgers from a few decades of misbehaving. His antics started at the 100th Kentucky Derby in 1974 when a bedsheet sign he made caught the attention of Sports Illustrated. The next year he smuggled a whole basketball court into the Churchill Downs infield for some entrepreneurial, unofficial Derby-day gambling. When that proved to be too much equipment, a couple of years later, he brought in that illegal volleyball court instead.

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Staring down at the documents that outline Anderson’s ingenuity is almost like looking at detailed records of a covert operation. Through these unsanctioned and oftentimes, down-right prohibited activities — or concessions, as he called them — his mission was to have a little fun at The Run for the Roses in a way that could also be profitable. 

Nearly 50 years after the fact, he invited me to see how year after year he dodged security and slipped equipment through the turnstiles at the track. 

By the time I left Anderson, I wasn't sure what was more impressive. 

One, that he'd brought that much contraband into Churchill Downs. Or two, that he'd documented it all. 

Constructing a basketball hoop or a volleyball court in the infield completely unnoticed is unthinkable in our modern world where Churchill Downs bans coolers, backpacks, balloons, confetti, frisbees and selfie sticks. The infield in the 1970s, however, looked quite a bit different while Anderson hatched out his first plan.

Not unlike today, security was diligent about searching for alcohol. Vessels like coolers, backpacks and duffle bags — which were allowed at the time — were rigorously searched for beer and liquor. Aluminum step ladders, however, were welcomed and oddly they were common enough in the infield to be inconspicuous. A half century ago, Anderson and his friends used a ladder as a rallying point of sorts in the infield.

He reasoned security would be less likely to search a ladder than a cooler. 

“The stepladder was just the mule to carry in everything else that was needed to set up the concession,” Anderson explained. 

Then he grinned and shared the whole plan with me in extreme detail as though he'd just hatched the scheme up yesterday. Before he arrived at the track on Kentucky Derby Day, he strapped the wooden beams for the basketball pole to the side of the ladder. He had to pass on bringing a backboard, of course, because that was just too big. Still he wedged the basketball hoop, a regulation size ball and an assortment of hardware and tools between the rungs. 

When that looked too obvious, he wrapped a blanket around the center of it to conceal all the odds and ends that made up the game. 

As he stepped up to the gate early on the morning of the Kentucky Derby, he kept his eyes peeled for uniform security, but no one stopped him. 

Anderson, his ladder and all the trimmings for his entrepreneurial shenanigans made it through the turnstiles without a question or even a second glance. Once he was in the infield, he took the shovel he’d packed in that ladder bundle and dug a hole two feet deep into the ground. 

He caught some suspicious glances at this point, but tried to stay coy. 

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What was he doing, people asked. 

“A project,” he told them. 

What kind of project, they wondered. 

“It’s a surprise,” he explained. 

As the sun rose higher in the sky as the morning went on, eventually, so did that basketball pole. He managed to dig deep enough that it rested firmly in the ground once it was secured by all that access dirt. By the time he threw the first basket, a few dozen people had gathered around him to watch the spectacle. 

They sprung for the rebound, and clamored about breaking off in teams. 

No, that’s not how this was going to work, he explained to the crowd.  

Instead, he walked off 15-feet and drew a line in the dirt with his foot. The rules were simple. You paid 25-cents to shoot the ball twice. If the player made both baskets, Anderson paid out 50-cents to the shooter. Otherwise, he kept the change. 

“But to be honest about it, not many good shooters played,” he told me.

“So I didn’t pay out that many 50 cents (prizes).”

Eventually his pockets bulged with coins and a few paper dollar bills, and he enlisted an infielder with a banking background to run to different betting windows and consolidate his earnings into $20 dollar bills. In one trip they brought back more than $80 in cash, he recalled. Those 25-cent shots added up.

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But as the afternoon rolled on, his game took on a life of its own as the growing crowd took on side bets. It slowed down the process and it cut into Anderson’s profits. 

“With the wagering and the side bets, that was the Achilles heel of the whole operation,” Anderson explained. “It was a lot of fun and it looked like a lot of fun, but it was a lot of work, too.” 

Still, he deemed the whole game a success. He managed to make some cash and earn a little notoriety. With his walk-in-like-you-own-the-place attitude, no one ever wondered whether he had the authority to be directing basketball in the infield. 

That confidence, however, was the downfall of his activities during the following year in 1976.

This time Anderson didn’t bother wrapping the blanket around all the odds-and-ends and materials wedged into the ladder. He reasoned he didn't need to, as no one stopped him before. But on his way into the track, he ran into one of the top officials at Churchill Downs. 

Anderson was afraid he and his basketball hoop were going to be trudging back to his parked car.

He had another idea, though. 

Oh he wasn’t trying to break the rules, he told the official, kindly. He’d been in the infield the year before and he’d seen another group of Derbygoers playing basketball. 

He figured it was allowed, he explained.

"Well they weren't supposed to do that," the official told Anderson, clearly not realizing he was talking to the mastermind from the year before. 

So rather than make him take all the contraband outside of the track, Anderson was invited into the general office where the maintenance manager was instructed to look after the ladder and all the tools.

Anderson didn't make any money off his game that year, but after all that, he still felt like a winner. 

“Because of the way he treated me, I felt like a celebrity on Millionaire’s Row,” he recalled. “It was magical. He was so nice, so considerate.”

For anyone else that might be the end of illegal gaming, but Anderson went back to the drawing board and came up with a new plan. Basketball required too many materials, but perhaps, there was another way to be profitable. 

In 1977, he skipped the stepladder all together and instead fastened the materials for a volleyball court beneath baggy overalls and a giant raincoat. 

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With boards strapped to his legs he marched toward the track turnstile like a toy soldier. 

“We get to the turnstile, and I clank through the turnstile,” he recalls. “Literally all the guys, who were with me had coolers and baskets and, stuff and the security immediately zeroed in on them.”

“I just slowly toddled off out of the security area and just kept walking.” 

Once he was in the infield he marked off a 30-foot-by-60-foot space using string. This time he asked players to break into teams of six. At the beginning of each game, the captains would gather $12 for the team. If they won the match, the team received $18 and Anderson pocketed the rest as profit. 

This wasn't nearly as lucrative as basketball, but it cut back on side betting and it required much less equipment. 

Different versions of volleyball and basketball played out like this over the course of the next 10 years so or. As Anderson and I flipped through the photos and the files, I saw different prototypes, rules and mechanics, but the whole operation came back to the principles of making a few dollars and having a little fun.

By the late 80s, Anderson gave up the elaborate rouses for sports and instead focused his energy on smuggling his own alcohol into the track. Eventually, he retired from illegal concessions and rouses completely, and he took on a more legitimate role as a limo driver. That was a great gig, he explained. Anderson didn't have to walk like a toy soldier, he still made some money and he was able to be around the excitement of the track. 

After we'd spent more than two hours talking, I finally had a grasp on just how many roles he had in the infield. 

What I didn't get, though, was why he'd kept records as intricate as though he was running a small business. 

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That goes back to one of his first attempts at infield tomfoolery during the 100th Kentucky Derby. His prize possession in all of his files is a copy of a Sports Illustrated magazine from May 1974, where his tendency toward absurdity received national attention. 

That was the year Princess Margaret of Great Britain attended the Kentucky Derby, and so to honor the occasion Anderson made a bedsheet sign that said "Hey Meg had any winners lately?"

He knew he'd never meet her, and he wanted to catch her attention.

"Infield common people meeting English royalty was not going to happen," he explained. "There’s no way we were going to cross paths except maybe through a visual element like this sign."

A week or so after the race, Anderson received a call from a friend insisting that he go pick up a copy of the issue where the 100th Derby was featured, and when he opened it, he saw his sign. Anderson never heard whether Princess Margaret actually saw it, but he did hear from the editor of Sports Illustrated. 

A little while later, he wrote to the magazine wondering if they'd like to tell a bigger story about that sign. Eventually, an editor wrote back to say the publication couldn't assign a writer to the project, but if Anderson submitted a manuscript, they'd be happy to review it.

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Offended, he never took them up on that offer, but that exchange inspired decades of notetaking and files. Most of it has stayed tucked away for more than 30 years. 

And it might never have left the boxes if it hadn't been for the pandemic. 

Anderson isn't really a big fan of computers. He doesn't know how to type, and when he does, he hunts and pecks across the keyboard. During the shutdown, though, the woman he dates, Susan Alvey, encouraged him to start organizing it. Two years later, they still haven't finished sorting through the whole collection, and there are still plenty of notes to uncover. 

Whether he ever turns these files into that manuscript Sports Illustrated suggested nearly a half-century ago remains to be seen.

He got a whole lot more than a pocket full of quarters when he built that basketball court though. He has boxes and decades' worth of wild, incredible memories. 

Features columnist Maggie Menderski writes about what makes Louisville, Southern Indiana and Kentucky unique, wonderful, and occasionally, a little weird. If you've got something in your family, your town or even your closet that fits that description — she wants to hear from you. Say hello at mmenderski@courier-journal.com or 502-582-4053. Follow along on Instagram and Twitter @MaggieMenderski.