: Against all logic, Lupita won, completing Whiteley's six-race accumulator and turning his £2 into £1.45 million . Fast Facts: Famous Wagering Feats
: Australian tycoon Kerry Packer once bet $4.6 million on a horse named Mahogany . The horse won, netting Packer a payout of approximately $20 million.
: At age 37, Larry King was broke with only $42 left. He bet his last dollar on a longshot filly at the track and won $8,000 , which helped reboot his career. Horse Betting
: By the time he retired, it is estimated Benter made nearly $1 billion through his quantitative betting models. The Longshot of a Lifetime: Winning Colors
A gripping true story involves three gamblers—Miami Paul, Dino Mateo, and Big Bernie—who bet everything on a filly named for the 1988 Kentucky Derby. : Against all logic, Lupita won, completing Whiteley's
: They unknowingly placed the wager with bookmakers linked to a drug cartel. When Winning Colors defied the odds to become one of the few fillies to win the Derby, the men had to figure out how to collect their winnings without getting killed.
: The trio placed a massive longshot bet at a racetrack in Tijuana, Mexico. : At age 37, Larry King was broke with only $42 left
: Whiteley entered the Exeter racecourse with a free promotional ticket and placed a modest £2 bet .