Churchill Downs Free Horse Racing Picks (05/29/23)

This upcoming Monday, May 29, 2023, Ron Raymond, a veteran sports handicapper, will be sharing his top horse racing picks for Churchill Downs. Known for his strategic approach to betting, Ron has a reputation for making savvy selections that take into account a variety of factors, from the horses' past performance records to the track conditions.

First up is Race #1, a maiden claiming race with a purse of $30,000. The post time is 11:45 AM, and the race covers a distance of one mile on dirt. Ron's “Win” pick is (5) Malibu Smart with 2-1 morning line odds and jockey M Garcia, who has a win rate of 32%. His “Place” pick is (1) Lucky Phoenix with 5-1 odds and jockey C J Lanerie, and his “Show” pick is (2) Origami Girl with 5-2 odds and jockey J Loveberry. In terms of exacta and trifecta picks, Ron recommends a 5/1, 1/2, 2/6 box for both.

Moving onto Race #2, a maiden special weight race with a purse of $92,000, post time at 12:14 PM covering 5 furlongs on dirt. Ron's “Win” pick for this race is (6) Woodcourt with 7-2 odds and jockey W A Rodriguez. His “Place” and “Show” picks are (8) Five o' Somewhere and (3) Gewurztraminer, respectively. For exacta and trifecta, consider a 6/8, 8/3, 3/5 box.

Lastly, we have Race #3, an allowance optional claiming race with a hefty purse of $127,000. This race begins at 12:43 PM and spans 1 1/16 miles on turf. Ron's top pick for this race is (7) Shoplifter with 4-1 odds and jockey M Garcia. His “Place” pick is (9) C C Cruise Control, and his “Show” pick is (4) Embrace Me. Ron's exacta and trifecta boxes for this race are 7/9, 9/4, 4/8.

As part of Ron's betting strategy, he's a fan of the “Double Dutch” system. This approach involves betting on one horse to win and/or place in the race. If your chosen horse ends up finishing second, you could potentially recoup your bet, depending on the odds. This strategy can be an effective way to mitigate losses while still allowing for significant potential winnings.

While we've covered some of Ron's top picks for the day, there are plenty more races to explore. For additional selections, consider signing up to access the Raymond Report premium horse racing tipsheet inside the member’s area. This valuable resource provides a more detailed breakdown of each race, including Ron's full array of picks. You don't want to miss out on these insightful tips and strategies. Sign up today!