Pimlico, Race 3: 11:41 a.m.
Pimlico, Race 5: 12:51 p.m.
Bourbon Stakes (G3) winner
Pimlico, Race 6: 1:28 p.m.
Maryland-bred Lewisfield is the heavy favorite in the Grade 3 Maryland Sprint Stakes for 3-years and upwards. Second choice is Proforma, followed by Wentz and Always Sunshine. Of those four, only Wentz is entering off a win, a pair of victories to be exact. Lewisfield and Wentz will go out for the early lead, so it could be a duel right out of the gate.
Pimlico, Race 7: 2:07 p.m.
Longwinded Ickymasho tops the 1 ½-mile Searching Stakes on the turf for fillies and mares 3 years old and upward. Trained by Roger Attfield, the 7-year-old mare will go out for the lead and dare her rivals to catch her if they can. Homeland Security will be one of those trying to run down Ickymasho and is perfect at the 12-furlong distance. Osare, a half-sister to none other than Arrogate, could make her seasonal debut here but is also cross-entered back home at Belmont Park. She was last seen winning the Dueling Grounds Oaks at Kentucky Downs and will likely join Ickymasho on the lead. Also worth taking a look at is Coachwhip, who was third behind Ickymasho in the Bewitched (G3) in her last start.
Pimlico, Race 9: 3:25 p.m.
Wesley Ward-trained Jo Jo Air is the lukewarm favorite in the five furlong The Very One Stakes on turf for fillies and mares 3 years old and upward. She most recently won the William Walker Stakes while up on the pace. She posted a quick 5-furlong work on May 12, indicating she is on her toes. Souper Echo has been in good form in 2019, compiling a 5: 1-2-1 record for the year. This will be a bit of a cutback for her, as she exits a 5 ½-furlong race. Misericordia has been flat so far this year, and I cannot justify taking her at 4-1. Wild About Star also has not been at her best recently but is perfect going 5 furlongs.
Pimlico, Race 10: 4:05 p.m.
Chad Brown will send out 3-1 morning line favorite Inflexibility in the 1 1/16-mile Grade 3 Gallorette Stakes for 3-year old fillies and mares on turf. The 5-year old Scat Daddy mare hasn’t won since April of last year but has been competitive in some of the bigger turf events for the division. Personally, I will take 10-1 Thewayiam on top. She has not won since March of last year, but she has a string of seconds in some huge races. She’s already had a start to knock the rust off this year, and I think Graham Motion has her ready for this spot. Mitchell Road steps up in class for this race but has done nothing but win in her last three starts. She likes the distance, but she will have to prove she can hang with the big girls. I’m on the fence about the two imports, Arnaud Delacour’s I’m So Fancy and Chad Brown’s Barkaa. The former is making her U.S. debut while the latter was no factor in the Sands Point (G2) back in September.
Pimlico, Race 11: 4:42 p.m.
The Grade 3 Chick Lang Stakes brings together 3-year old sprinters, topped by favored and undefeated Preamble. This will be the speedy colt’s graded debut, but he has proven to be gutsy, encountering trouble yet prevailing in two of his three career starts. Also undefeated is Pyron, who posted back-to-back 100 Equibase speed figures in his two lifetime starts at Oaklawn. Grade 3 winner Gladiator King is in sharp recent form, reeling off two stakes victories leading up to this spot. Also on a winning roll is Malpais, who trainer Joe Sharp wheeled back to sprints after failing to stretch out in the Lecomte (G3). These four are all on or near the lead types, so it could get heated in this six furlong event.
Pimlico, Race 12: 5:39 p.m.
Dual threat Catholic Boy returns in the 1 1/16-mile Grade 2 Dixie Stakes for 3-year olds and upward on the turf. Last year this son of More Than Ready won the Belmont Derby (G1) and the Travers (G1) prior to a poor run in the Breeders’ Cup Classic. This may not be his best distance, and he might be a bit rusty, but he could very well still be my single for the day. He has the advantage of drawing the far outside, giving him the opportunity to either go for the lead or sit back off the pace, though I suspect he will make his own racing luck. Aside from him, you have to like Inspector Lynley, who Shug McGaughey has in good form.
Pimlico, Race 13: 6:48 p.m.
Now that we’re past the debacle that was the Kentucky Derby, we can focus on the Preakness Stakes. Neither “winner” shipped to Baltimore, resulting in a nearly full field at Pimlico. Bob Baffert’s Improbable gets top billing off a fourth-place (after the disqualification of Maximum Security) run in the Derby. I am going with War of Will. He ran a great race in the Derby but had the misfortune to get tangled up with Maximum Security at the quarter pole. He should get an ideal trip from the rail. Anothertwistafate has only won on Golden Gate’s synthetic surface, but he gave a good accounting of himself in his last two starts, both runner-up finishes on the dirt. I don’t see him winning this, but he could certainly fill out the exotics. Upstart Alwaysmining has reeled off six straight victories and has been nowhere near losing any of them. This will be a huge step up in class for the Kelly Rubley trainee, but you have to like a talented local. Warrior’s Charge is an interesting new-shooter. He really relished the stretch out and the switch to a front-running race style. Since then, he has won his races by open lengths. He will likely keep War of Will company on the front end.
Pimlico offers nine stakes races spread over the entire card. The most lucrative sequence of the day is probably the $2,000,000 guarantee $0.50 Pick 4 encompassing races 10-13, so we’ll stick with that. I will try to single Catholic Boy in Race 12.
On a budget, play: 2, 3/ 7, 8/ 12/ 1, 4 = $4. If you hit this, it obviously will not pay much.
If you have a bit more to play with, try: 2, 3/ 3, 6, 7, 8/ 12/ 1, 4, 7 = $12
For full coverage of those that I think have a shot, play: 1, 2, 3, 4, 9/ 3, 6, 7, 8/ 11, 12/ 1, 3, 4, 7, 12 = $100