For the brunt of the 20th century and the early portion of the 21st century, sports betting was done in the shadows of American culture. It was bookies. It was back-alleys. And it was always done in the dark, and with a whisper.
One day each year though—the first Saturday in May—things felt different.
Flowers were blooming, the sun was bright, and there was no shame in openly talking about betting.
“Hammerin’ Hank” Goldberg would do a lengthy Saturday morning spot on SportsCenter, and he would openly speak on things like “the morning line,” “exactas,” “trifectas,” “superfectas,” and “show bets.”
The first Saturday in May—Kentucky Derby day—was the one day of the year where betting on sports didn’t feel scandalous.
The Derby, without question, helped make sports betting a respectable activity in the US. The pageantry of the event—with the flamboyant hats, elegant dresses, expensive suits, and the mint juleps—made horse racing, and subsequently horse betting, acceptable to most.
“Horse racing has always had this sheen of respectability,” said David Bockino, Associate Elon University Professor and author of the upcoming book, Over/Under: An Unexpected History of Sports Betting. “The idea that you dressed up for the event in some capacity, the idea that you drank fancy drinks. The idea that this was an ‘outing’ made the underlying betting foundation more acceptable to American society. Everyone looks nice when you turn on the television [to watch the Derby]. That sort of facade was built up around horse racing and the event over the years … but in the end, it’s really just a betting endeavor.”
Simplicity is Key
The simplicity of horse racing makes it appealing to a broad audience. You pick a horse to run faster than the other horses. Easy peasy.
You don’t have to worry about spreads, or Over/Unders, or juice.
“So many people just put the names of the horses in a hat and bet like a nickel or a dollar. I do this with my family, with my kids on Derby day. It’s just part of the day,” Bockino tells Complex. “Over the years it just became, ‘hey, this is what we do for the Kentucky Derby.’
“And horse racing, in general, is just tailor-made for betting. Horse racing is just perfect. There’s 20 horses or 10 horses … whatever number. And all you do is pick one and root for it. It doesn’t get more simple than that. You attach yourself to one of these animals and cheer for them for two minutes.
“It’s also low effort. You don’t have to do much, and when it’s over you’re like, ‘hey cool, I won 100 bucks’ or more likely, ‘ah man, I lost 5 bucks.’”
Pool Party
Horse racing betting is different than traditional sports betting in that it operates under a parimutuel system. Parimutuel betting is “pool betting” where you’re betting against other people in a giant pool. Traditional sports betting, meanwhile, involves betting on fixed odds, and you’re betting against a sportsbook (or against a bookie, back in the day).
Parimutuel betting felt much more transparent and safe for most people years ago than doing business with a bookie.
“Bookmakers were often super shady back then,” Bockino tells Complex. “Bookies would have their own quirks and be trying to pull the wool over your eyes. Parimutuel betting was different because … it’s like prediction markets today in a lot of ways … because you’re betting against each other. Because the house was taking a guaranteed cut, that almost made it more acceptable.
“It’s like, ‘they’re not trying to screw you over like the bookmaker,’ they’re just offering this service and then taking their cut upfront.”
A New Betting World
Today, you can bet from the comfort of your couch. Gone are the days of sketchy phone calls to random numbers, and shady meeting locations.
The Kentucky Derby has helped America’s collective psyche embrace sports betting over the years, but Bockino says that the love of placing a bet has always been there.
“People were always ready to bet [on sports],” Bockino said. “There hasn’t been a great societal shift in people wanting to bet on sports. There’s just been a great technological shift where you can now bet on your phone. You can bet on horse racing, or a table tennis event in China. Technology has made betting so much easier. But people have always wanted to and have always found a way to bet on sports. If you look back at the origin of any American sport, there were people betting on the outcomes from the very beginning. Horse racing included.”
David Bockino’s book, “Over/Under: An Unexpected History of Sports Betting” will be released on June 2, 2026.
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