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‘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

Breeders’ Cup Launches Free-to-Play Kentucky Derby Online Contest

The Breeders’ Cup, one of Thoroughbred racing’s most prestigious international events, launched a new fan contest tied to the 147th Kentucky Derby Presented by Woodford Reserve at Churchill Downs on Saturday, May 1.

Gambling

Live Longshots for the 2021 Kentucky Oaks and Kentucky Derby

On big race days, a big part of the appeal is that large, competitive fields provide a great opportunity to uncover live longshots, and the Longines Kentucky Oaks and Kentucky Derby Presented by Woodford Reserve on April 30 and May 1, respectively, at Churchill Downs are the definition of bi

Gambling

Making Money Betting the Favorite in Kentucky Oaks

At first glance, Friday’s $1.25 million, Grade 1 Longines Kentucky Oaks appears to be an absolutely wide-open event. Held over 1 1/8 miles at Churchill Downs, the historic race for 3-year-old fillies has drawn a full field of 14, with many bringing elite credentials to the table.

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