Horse Betting -

: For his final leg, he picked a horse named Lupita, which had lost its previous 28 races.

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. Horse Betting

: Their journey back across the border, evading both federal agents and potential killers, was later chronicled in the book The Greatest Gambling Story Ever Told . The Heating Engineer’s £1.5 Million Miracle : For his final leg, he picked a

: He won a staggering $13 million but intentionally never claimed the ticket. The unclaimed winnings were eventually donated to charity by the Hong Kong Jockey Club. The Heating Engineer’s £1

: 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.