Matt Winn Stakes (Churchill Downs) Predictions, Picks & Betting Odds

Matt Winn

If you're playing only to win, go with my top pick Helium (5/2)

Post Position and Odds – Matt Winn

Check out our predictions and odds for the Matt Winn at Churchill Downs!

PP Horse Odds Jockey Trainer
B J Hernandez Jr N Pessin
2 HELIUM 5/2
J Leparoux M Casse
3 O BESOS 2/1
M Pedroza G Foley
C Lanerie D Romans
F Geroux B Cox
F Arrieta C Caramori
J Talamo D Romans
D Cohen R Diodoro

Best Bets for the Matt Winn

Here are my plays ($50 in total)

$40 win – Helium = $40

$5 Exacta box – Helium and Ready to Pounce = $10

Matt Winn Top Pick

Odds provided by TwinSpires. Click below to head to the sportsbook and place your bet!

Our Pick
Helium (5/2)
Best Pick Odds provided by TwinSpires
Helium (5/2) Bet Now

O Besos and Helium, two horses who did not exactly embarrass themselves in the Grade 1 Kentucky Derby, headline a field of eight 3-year-olds set to run in Saturday’s Grade 3 Matt Winn at Churchill Downs.

A 3-year-old son of Orb, O Besos announced himself as a potential live longshot for the Kentucky Derby when he rallied up the rail to finish third behind Hot Rod Charlie and Midnight Bourbon in the $1 million Louisiana Derby. Sure enough, the Greg Foley-trained chestnut made a solid move at Churchill Downs, before flattening out a bit late to finish 5th of 19 horses on the first Saturday in May.

Meanwhile, Helium was also a longshot in the Run for the Roses, following a planned eight-week layoff which came after a solid score in the Grade 2 Tampa Bay Derby. A winner of both of his starts at 2 for Hall of Fame trainer Mark Casse at Woodbine, the son of Ironicus went down to defeat for the first time in the Kentucky Derby. Prominent early, he faded to finish eighth in the spring classic.

Chief among the rivals to the pair exiting the Kentucky Derby is the Brad Cox trained Fulsome. After winning 1-of-4 starts to begin his career on the turf, the Juddmonte Farm homebred has been perfect in two starts, including a last-out win in the $300,000 Oaklawn Stakes on May 1. Before that, the son of Into Mischief scored at Keeneland in his main track debut.

How to Watch the Matt Winn

Matt Winn Race Information
What Matt Winn (Grade 3)
Location Churchill Downs
Time Saturday, May 29 — 4:55 pm Eastern time
How to Watch TVG
Purse $150,000

Race Analysis

O Besos

If you follow these pages religiously, you know this late-running son of Orb was my top longshot in the Kentucky Derby. Despite not quite being able to sustain his rally the final eighth of a mile, he did outrun his 41/1 odds to finish a respectable fifth. Stabled at Churchill Downs for trainer Greg Foley, it makes sense that he would use the Matt Winn as his first race since the big one.

His last two performances, which also include a very good third in the Grade 2 Louisiana Derby, point him out as a tough customer and the likely favorite. This time around, though, I am going to lay off him. Dropping down to the 1 1/16-mile distance for the Matt Winn, I believe it might be difficult for him to pick up all the pieces coming out of the 10 furlongs Derby. An obvious threat to win, I am going to try to beat him as the favorite.


The other horse to run in the Derby is the one I believe might be better suited for the shorter distance which they will find on Saturday. Helium has enough tactical speed to lay close, as he did in both 7 furlong wins as a juvenile, as well as the 1 1/16-mile Tampa Bay Derby. This should allow him to be ahead of O Besos early and get first crack at the early leaders.

As for his Derby loss, I liked what I saw. It was only his second start of the year, and he was in striking distance for the first mile plus. Given the experience of that tough race in the Derby, I look for the lightly raced son of Ironicus to move forward. In fact, I expect him to thrive at the middle distance. Also stabled at Churchill Downs, he is my top pick.


While the top two have both been tested against the best of the crop, this one will be stepping up in class on Saturday. Undefeated in two starts on dirt, the son of Into Mischief was a solid grass performer early in his career, but looks to be even better on the main track. Perhaps coming in off easier races will prove to be an advantage, but I have a feeling that he will get a lot of play to be bet near the two Kentucky Derby runners. At the odds, I will wait and see on this before betting him against more proven commodities.

Ready to Pounce

This one has some things in common with Fulsome, as he started his career on turf, before looking very good when transitioning to dirt. Unlike that one, however, he has only run twice in his career. Too far back while sprinting in his career debut, he did make up good ground to finish fourth. The More Than Ready colt came back six weeks later and showed much more early speed to stalk and pounce in a good-looking win at Keeneland. Similar tactics could prove beneficial in a race without much speed. It is a major step up in class, but I find him to be an interesting up and comer.

Sittin On Go

The most experienced stakes performer in the race is one of two from trainer Dale Romans. He should be respected as a former stakes winner at Churchill Downs, but that one came six starts ago, and he has not hit the board since. Having said that, this could be his easiest spot in a while, and his last race was improved, when finishing fifth in the Grade 2 Pat Day Mile. Still, his lack of serious competitiveness in six straight-stakes tries has me unwilling to like his chances.

Hello Hot Rod

I’m not sure why he was so far back early last time when he finished fourth in the Federico Tesio at Pimlico, but at least he finished with some energy. Before that, he showed consistent and successful speed, including minor stakes win at Aqueduct. Saturday’s test will tell us if he can compete with this level of horse, which is yet to be determined. But if he goes right to the lead, I believe he could prove to be a live longshot to stick around for the exotics.

Game Day Play

In his first start for new connections, he ran a decent race to finish third behind Fulsome in the Oaklawn Stakes. While the winner of that race seems to be a horse moving forward, it is hard to say the same about this one, who has already had plenty of chances against a bit lesser. He did win a stakes race last year, but this Matt Winn looks to be a little tougher than he has already been losing against. Not completely out of it, but he’s not for me in here.

Southern Passage

This son of Super Saver, like his Dale Romans stablemate, also has little early speed. It doesn’t seem to be an advantageous style for a race without much speed. On top of that, Sittin on Go looks like the classier of the two. His last was an improvement, but I still find him hard to recommend in this spot.

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