Triple Crown

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Betting a 10-1 Longshot in the 2021 Kentucky Derby

For handicappers, there’s no greater satisfaction than betting a longshot and seeing your unheralded selection take first prize. Whether it’s a $5,000 claiming race at Mahoning Valley or a Grade 1 stakes, beating the odds and uncovering a longshot winner is much more satisfying than betting a bevy of favorites.

Gambling

2021 Kentucky Oaks at a Glance

The Return to Normalcy Tour at Churchill Downs starts Friday when the Longines Kentucky Oaks returns to its traditional spot on the eve of the first Saturday in May. A field of 13 will be on hand for the famed Grade 1 stakes that has once again attracted a stellar collection of the best 3-year-old fillies in training and turned the 1 1/8-mile stakes into a highly attractive betting affair.

‘Mattress Mack’ McIngvale Set to Make Multi-Million Kentucky Derby Wager

If Jim "Mattress Mack" McIngvale gets his wish, many people will be sleeping comfortably the evening of May 1 – himself included.

Gambling

Top Win Contenders in 2021 Kentucky Derby

Back at its traditional place on the calendar on the first Saturday in May and using the new 20-horse gate for only the second time in history, Saturday's 147th running of the $3 million Grade 1 Kentucky Derby presented by Woodford Reserve is expected to be a very competitive event.

Gambling

Derby Diaries: Patrick O’Neill Describes ‘Unbelievable’ Ride to Derby With Hot Rod Charlie

Patrick O’Neill, nephew to two-time Kentucky Derby-winning trainer Doug O’Neill and top bloodstock agent Dennis O’Neill, had a different interest from most college kids when he was an undergraduate student and a member of Brown University’s football team. He insisted on adding TVG to the fraternity house’s cable television package; he was the one who watched horse racing at every opportunity, including in class, and in film study prior to practice.

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