Let's see you say the headline 3x fast...
I had zero success with my Kentucky Derby Pick 5 plays, but I've mapped out Saturday's Pick 5 sequence from Races 9-13, culminating in the Preakness Stakes.
If playing the undercard, here are some thoughts on Races 9-12.
I'll post wagers on Saturday once it's clear whether the grass stakes remain on the turf; too early to tell with rain in the forecast.
Race 9, James W. Murphy Stakes (3:30 p.m. ET)
I sense that a few connections will be doing a rain dance in hopes of this one getting washed off the turf. If that happens, the only play is #2 Copper Tax, who has been crushing foes on the Maryland circuit. Did nothing against the likes of Dornoch and Sierra Leone in the Grade 2 Remsen at Aqueduct in December but deserves a pass vs. Saturday's field, which is way inferior. I'd use him and elevate #5 Speedyness (10-1), a fellow Maryland-based horse, if on a wet dirt track. If the race stays on turf as carded, it's a complete crapshoot as about half the field of 12 has never run on grass and the others are not very good. I'll side with #4 Twirling Point (4-1) as best on turf. Premise is simple. After hopping out of the gate in the Rushaway at Turfway Park on March 23, Twirling Point gathered himself and made a late stretch charge, finishing third by a half length to Trikari, who took the Grade 2 American Turf Stakes at Churchill on Derby Day. The transition from a synthetic surface should be no issue and I sense that Twirling Point is the classiest turf runner and has the most upside. I'm speculating, too, that runners 7, 9, 10, 11 and 12 (morning line odds between 4-1 and 8-1) will all take money if contested on turf, signaling that Twirling Point can maintain odds around 4-1, making him playable on the win end and will consider singling to start my Pick 5 ticket.
Race 10, Sir Barton Stakes (4:10 p.m. ET)
Unless heavy rains wash races off the turf, this is the first of two dirt races in the sequence, with 10 horses slated to run one and one-sixteenth of a mile. The favorites (#5 Corporate Power, 9-5, and #8 Tuscan Sky, 5-2) seem beatable and both are wearing blinkers for the first time, which is peculiar. The two I'll use are #10 Imperial Gun (7-2) and #4 D Day Sky (15-1). Imperial Gun was aggressively placed in the Grade 1 Arkansas Derby and got drifted out badly in the early backstretch by a horse but kept trying and finished 7th to the likes of Muth, Just Steel and Mystik Dan. That level of foes gives him an edge here vs. much softer competition. In the race prior, he lost to Pat Day Mile winner Seize the Gray, so logically he's faced the best foes in this field yet shown a penchant to be one-paced. Joel Rosario returns to ride after guiding Imperial Gun to his maiden victory and close second in a minor stakes at Oaklawn Park.
Meanwhile, D Day Sky is worth taking a flier. Switched last race to a new (winning) barn and, though it was against fellow maidens, seemed to mature after about a three-month break and without blinkers a first time. Not incredibly stiff competition but he took decently to the extended 9-furlong distance and his two best (of five) races were at two turns, including a third-place finish vs. Derby entrant and stakes winner Track Phantom in late November. Irad Ortiz rides and is a significant upgrade from the likes of Eddie Perez and Chris Landeros, who rode him before Kendrick Carmouche's expert handling in the maiden score at Aqueduct on April 5. D Day Sky definitely deserves a look.
Race 11, Jim McKay Turf Sprint (4:53 p.m. ET)
It's a 12-horse field that I've narrowed to two potential winners and give #11 Witty (9-2) the edge over #12 Beer Can Man (5-2). The latter is a hard-knocking six-year-old that has competed well in numerous graded stakes and takes a big class drop here from the Grade 2 Shakertown at Keeneland in early April in a bid to repeat as Turf Sprint champ. Post 12 shouldn't be a huge detriment to a horse of this caliber in a lesser field. Yet I'm more intrigued by Witty, who won a local stakes in his 2024 debut at Laurel Park and does his best running late, which should be a factor in a race with tons of early speed.
Race 12, Dinner Party Stakes (5:52 p.m. ET)
I lack strong conviction in picking a winner but will use #10 Emmanuel (5-2) and #1 Highland Chief (12-1). This 9-furlong turf race has 12 runners and a lot of big, established names yet lacks a pound-the-table bullish favorite. Emmanuel boasts a Grade 2 and several Grade 3 (condition for this race) wins and is 7-for-14 lifetime for trainer Todd Pletcher. Emmanuel was overmatched in April's Grade 1 Makers Mark at Keeneland but won at Gulfstream on March 2 in a stylish and stalking pattern; expect similar in the Dinner Party. Assuming a good gate break, expect Emmanuel to sit third or fourth behind pacesetter long shots #12 Funtastic Again (12-1) and #8 Helms Deep (50-1). Another that could sit a similar trip is Highland Chief, a 7-year-old with lots of back class, including the Grade 1 Man O'War Stakes at Belmont, though that was in May of 2022. He ran 4x after that win but was kept in the barn for about 18 months before surfacing in the Grade 2 Elkhorn at Keeneland last month. Chief got an odd ride from John Velazquez, who strangled his keen horse in the backstretch and made a nice move into the homestretch but flattened as one might expect of a long layoff horse. I see the rider change to local jockey Jorge Ruiz as a potential positive, assuming he lets Highland Chief get into the race earlier. I don't see the distance as a problem and would consider a win wager on this veteran horse.
Race 13, Preakness Stakes (7:01 p.m. ET)
Full horse-by-horse analysis is below, but I'm singling #8 Tuscan Gold (8-1). I'm willing to die on the hill for this one and dislike the other seven, assuming the Derby Day runners will look fatigued and the other new shooters are subpar.