Penn Mile (Penn National) Predictions, Picks & Betting Odds

Penn Mile

If you're playing only to win, go with my top pick Annex (2/1)

Penn Mile Post Position and Odds

Check out our predictions and odds for the Penn Mile at Penn National!

PP Horse Odds Jockey Trainer
J Bravo M Stidham
J Velazquez J P Terranova II
3 ANNEX 2/1
J Alvarado W Mott
K Carmouche M Maker
J Rodriguez J Ness
S Russell J O’Dwyer
I Ortiz Jr W Ward

Best Bets for the Penn Mile

Here are my plays ($54 in total)

$10 Exacta part wheel – Annex over Chess’s Dream and Outadore = $20

$5 Exacta part wheel – Chess’s Dream and Outadore over Annex = $10

$2 Exacta box – Annex, Chess’s Dream, and Gershwin = $12

$2 Exacta box – Annex, Altidore and Gershwin = $12

Penn Mile Top Pick

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

Our Pick
Annex (2/1)
Best Pick Odds provided by TwinSpires
Annex (2/1) Bet Now

Led by multiple stakes winners, Outadore and Annex, a field of seven 3-year-old males have been entered for the eighth running of the Grade 2 Penn Mile set for Friday evening on the turf at Penn National.

The likely favorite for the $300,000 test is Outadore. Trained by Wesley Ward, the son of Outwork was a winner most recently in the Animal Kingdom Stakes at Turfway Park in his first start at 3. Last season, he was twice a winner on the turf, including the Juvenile Turf Sprint at Kentucky Downs. He also finished third in the Grade 1 Breeders’ Cup Juvenile Turf at Keeneland last November.

The second choice for the Penn Mile will likely be Annex, hailing from the Hall of Fame barn of Bill Mott. The chestnut son of Constitution began his career in January and won three straight, including a pair of stakes races on the Gulfstream Park turf. His winning streak came to an end last time when he finished eighth, beaten only five and a half lengths, in the Grade 2 American Turf on the Kentucky Derby day card at Churchill Downs.

Of the rest, the Mike Maker trained Chess’s Dream figures to get the most betting attention. A winner of the Grade 3 Kitten’s Joy in January, he is the most experienced horse in the race and finished just ahead of Annex last time in the American Turf.

How to Watch the Penn Mile Race

Penn Mile Race Information
What Penn Mile (Grade 2)
Location Penn National
Time Friday, May 28 — 7:46 pm Eastern time
How to Watch TVG
Purse $300,000

Race Analysis


This speedy son of Outwork has been a very consistent performer on multiple surfaces but has especially shown a fondness for the turf, where he’s won 2-of-3. He’s also proven his class, consistently having faced good horses. A winner of all three of the sprint races in which he competed, he twice tried to stretch his speed to the mile distance, only to come up short in the stretch run. With his class, and a sharp return win under his belt, he is an obvious threat on Friday evening, but with other speed signed on, I believe he is a vulnerable favorite.


Despite only a middle-of-the-pack finish last time against a deep field for the American Turf, I still believe this one is a very capable turf horse. A sharp winner of his debut to begin the year, this Bill Mott-trained runner came back to score consecutive stakes wins in his next two starts. It’s worth noting that all three of those wins came over the same Gulfstream Park turf course, but it’s likely he will be able to carry that form to other turf courses.

Without much early speed, he is dependent on having some pace to run at, but I expect the fractions to be solid on Friday. I also believe he will benefit from far less traffic, with only seven horses in here, than he experienced last time at Churchill Downs. Junior Alvarado, who rode him in all three wins, will be back in the saddle in the Penn Mile. He is my top pick.

Chess’s Dream

Another one with very little early speed, he should enjoy a quick pace as well. He’s never run a bad race in seven career turf starts and has actually split decisions with my top pick. I do believe that of the two, Annex has more upside, but it is hard to argue with his consistent rally. He is also a graded stakes winner at the one-mile trip which he’ll see on Friday. With a little better odds than the two favorites, he is a must-use in the exotics.


Kentucky Derby-winning jockey Johnny Velazquez hops aboard this son of Quality Road for the Penn Mile. His dirt form has been bad, but he’s run well in each of his three turf starts. After a maiden win at Aqueduct last fall, he came to the turf to finish third in a pair of stakes races in his most recent effort. In each turf start, he went to the lead, but I think that will be tough with Outadore and others in here. For that reason, I like others better.


Another who looks to have plenty of early speed will be making both his turf and stakes debut on Friday. On top of that, he’s only run twice a lifetime, both coming in maiden sprints. The good news for the son of Not This Time is that they were both good efforts, giving hope that he has the ability to become a stakes performer. Still, with the classy other speed in this race, this looks to be too much of a jump up to get excited about his chances in the Penn Mile.


This one will be my top longshot. Like Sibelius, he will be making both his turf and stakes debut on Friday evening, but unlike that one, he has more experience and has already run the mile distance in his last two starts. It will be a step up in class, but he has finished in the money in each of his four starts and has the ability to pass horses. He’s also shown some fights in his races. If he can take to the turf, he looks dangerous. His pedigree says he should develop into a very nice horse.

The King Cheek

This New York-bred has twice tested stakes company before and finished far behind both times. A son of Laoban, he too will be making his turf debut on Friday. It just seems that he is a horse who can compete with a lower level, but not with this type of class. Having said that, he could well add to the early pace, as he has shown good speed while sprinting. Hard to recommend for a strong showing down the stretch, though.

Bet on Penn Mile Here!

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Brian Zipse

Expert on Horse Racing

Taken to the races at a very young age, Brian has been a passionate fan of horse racing his entire life. Professionally, his work has been published on several leading industry sites. Brian served as the Editor of Horse Racing Nation from 2010-2017, where he still writes a regular column and hosts the popular weekly webcast HorseCenter.

Email: [email protected]