The summer is upon us and there is nothing better than lounging by the pool on a hot day while thinking about winning big in the casino at night.
In this article, we are excited to highlight a few of our favorite gambling getaways where you will find resort-style amenities and hot gambling action to keep you busy. Enjoy!
Whether you are in the shadows of Churchill Downs’ famed twin spires, amid the rolling bluegrass fields of Keeneland or most racetracks across the country, horse racing has always been about more than money. It’s about the roar when your longshot surges down the stretch, the shared excitement with buddies on a group bet, and the fair chance that a sharp handicapper can beat the game. But for growing numbers of everyday bettors, that magic is fading. A controversial practice known as Computer Assisted Wagering (CAW) is reshaping the sport—and leaving many players frustrated enough to walk away.
Thoroughbred racing’s elite trainers are judged by a demanding trifecta of metrics: total career purse earnings (a direct measure of the quality and market value of their horses), overall win totals (proof of volume, longevity, and day-in-day-out excellence), and success in the Kentucky Derby plus the other Triple Crown races (the ultimate test of preparing champions for racing’s most iconic stages). Data from Equibase through early 2026, combined with official Kentucky Derby and Triple Crown records, highlight a clear pantheon of modern legends who have dominated these categories. While historical figures like Ben Jones (six Derbies) or Sunny Jim Fitzsimmons (two Triple Crowns) set early benchmarks, today’s purse inflation and expanded racing calendars elevate those who combined volume with elite performance.
Annually, the Kentucky Derby produces some of the largest betting pools in the sport. Last year’s Derby race win, place and show pool totaled $122.4 million, while the exacta pool reached $30.1 million, the trifecta pool handled $35.5 million and the superfecta pool totaled $15.5 million. New on Kentucky Derby and Kentucky Oaks Days in 2026 will be a 50-cent All Turf Pick 4, while opening day of the Spring Meet will introduce the Jackpot 8, Odd vs. Even wagering and Matchup wagering.
Louisville, KY., (April 21, 2026) – Churchill Downs Incorporated announced that it has entered into a definitive agreement to acquire the intellectual property, including all trademarks and associated rights, of the Preakness Stakes and Black-Eyed Susan Stakes (the “Preakness IP Rights”) from 1/ST Maryland LLC, an affiliate of 1/ST Racing, for a purchase price of $85 million, subject to customary closing conditions.
