Horse Racing

How to bet the 145th Kentucky Derby: Liam Durbin handicaps the first leg of the Triple Crown

Kentucky Derby entrant Maximum Security is ridden during a workout at Churchill Downs Wednesday, May 1, 2019, in Louisville, Ky. The 145th running of the Kentucky Derby is scheduled for Saturday, May 4.

With the scratch of morning-line favorite Omaha Beach, a Kentucky Derby that looked to be a wide-open affair got a little bit murkier.

Improbable will get some betting that would otherwise have gone to Omaha Beach, by virtue of the fact that he just narrowly lost to Omaha Beach in the Arkansas Derby last time out.


Last year’s 2-year-old champ, Game Winner, will likely become a tepid favorite. Since his Breeders’ Cup Juvenile win over this track in November, he has two solid second places and no poor efforts. But he comes into this one fresh off a defeat in the Santa Anita Derby at the hands of Roadster, who has won three of four lifetime starts.

The track conditions are expected to play a part in the outcome, with rain predicted right up to Saturday. The track should be muddy or sloppy. Such conditions typically favor the early speed horses, and there are not many of those to choose from this year.


The sole speed in the race appears to be Maximum Security. He should burst to the lead from an easy seventh post position, settle down on the rail before the first turn and try to establish a lead of a few lengths while setting as soft of fractions as possible.

He is undefeated in four starts, so we might not have seen the best of him yet. If he is tested on the lead, he will need everything he has to hold on for a win. At 8-1 on the morning line, he looks like a great value play for a horse that has never lost and might get to the third turn with no mud on his face.

For even more value, consider War of Will. He was expected to romp in the Louisiana Derby. A switch from turf to dirt had him on a three-race win streak. But he found tons of traffic problems in that one and threw in the towel early. The Derby is not a good race to hope for no traffic problems, but maybe War of Will and his jockey both learned something from that race and can make some corrections for today. At 15-1, he seems to be unfairly penalized for that one race.

The favorite should go off no shorter than 9-2, so spreading bets around to find some value is a good idea.

Win bet: Maximum Security

Exacta bet: Box Maximum Security, Game Winner, War of Will and Long Range Toddy

Trifecta bet: Box Maximum Security, Game Winner, War of Will and Long Range Toddy

Liam Durbin is owner-handicapper of He shares his Triple Crown picks and betting tips with The Baltimore Sun each year.