Oaklawn Handicap Picks

#4 Skippylongstocking (5/2) – The son of Exaggerator for trainer Saffie Joseph Jr. has become one of my favorite horses in this division as he runs often and honest. The starter of 30 career races has won 10 of them and finished in the money 19 times while earning over $3 million. Not bad for a $37,000 purchase at the OBS April sales back in 2021. I often discuss my hesitancy betting on Joseph Jr. horses when they run outside of Florida, but this is a horse whose form has traveled with him no matter where he goes and he also had a career-best performance in this race last year when he trounced a field that included Highland Falls who wound up winning the Jockey Club Gold Cup (G1) later that year. Additionally, Saffie has been on fire at Oaklawn this meet winning six of his 11 entries. From a tactical standpoint, it is intriguing that Joseph Jr. has both Skippy and Alexander Helios in the race as they possess similar riding styles and are legitimate contenders to win. Jockey Irad Ortiz Jr. comes to town to pick up the mount for Skippy as his regular jockey, Tyler Gaffalione, broke his ankle in a paddock incident at Gulfstream Park about a month ago. Ortiz Jr. has ridden Skippy once before to a sixth-place finish in last year’s Breeders’ Cup Dirt Mile (G1), which was a 13-horse field where he broke from the far outside. For Saturday, the horse is third back in the form cycle and is coming off a victory in the Challenger (G3), which he won for the third consecutive year. He is looking to repeat winning this race and should sit an ideal trip just off the early pace where he is able to make a move. It will be interesting to see who ends up going off as the post time favorite between him and First Mission.

#3 First Mission (2/1) – The Godolphin owned and bred son of Street Sense has always had big expectations, particularly after winning the Lexington (G3) in his third career start. Over the next two years he added a pair of graded stakes wins to his resume in the Essex (G3) and Alysheba (G2), while falling just a nose short of winning the Clark (G2). He has thoroughly disappointed each time he stepped up to face Grade 1 competition as he lost those three attempts by a combined 31 ¼ lengths. However, this is the sort of field he should be able to handle on Saturday and he should also sit an ideal trip under the guidance of jockey Flavien Prat who takes over for Florent Geroux. There is not much speed to his inside, so look for Prat to make it over to the rail and sit a pocket trip behind Banishing and Alexander Helios while matching strides with Skippylongstocking. He came up a little short last time out in the Razorback (G3), but that is to be expected given it was his first start in over six months. He is now second back from the layoff from a trainer who has impeccable numbers under those conditions and has put in five official workouts since that February loss. He should be fit and ready to run on Saturday. It is also promising to see that he has won over the track and posted a strong 102 Beyer Speed Figure (BSF) in his return two months ago, which makes you think he could take a step forward from that number in his next start. It is hard to decide between the top two choices who are both very logical, but he will be included in my Late P5 ticket and depending on his price at post time, he might also be on a few win tickets.

#2 Disarm (10/1) – I am not sure there is a horse that has been more consistently overhyped than Disarm, but I also think he makes a lot of sense in this spot, and it is possible he ends up representing the best combination of price and chance to win. The son of Gun Runner was a consistent presence on the Kentucky Derby trail two years ago and finished fourth in the Run for the Roses. He came back to win the Matt Winn (G3) over a sloppy track before finishing fourth in the Jim Dandy (G2) and second in the Travers (G1) to eventual champion three-year-old male, Archangelo. Trainer Steve Asmussen sent him to the bench for eight months following that runner-up effort and there was a significant amount of buzz regarding his return to the track with people speculating he could be a Breeders’ Cup Classic winner. Rest assured, that didn’t happen. He won his first race back in 2024, which was an $80,000 optional claimer he took in gate-to-wire fashion while earning a modest 85 BSF. From there he lost his next four races by a combined 24 ¾ lengths while never finishing better than a distant third. Despite this, he still went off as the odds-on favorite in races like the Lukas Classic (G2) while finishing behind the likes of Hit Show, Cooke Creek, and Rattle N Roll. Asmussen again sent him to the bench for six months and he returned in March, eeking out a victory over Bendoog in another $80,000 optional claimer in which he ran with Lasix. I am not sure we will ever get the triple-digit BSF version of Disarm again when he runs off Lasix, but this race sets up beautifully for him and jockey Keith Asmussen. I am not a huge fan of putting the Asmussen sons when they ride for their dad, particularly in a big race, but Keith got the job done with this horse last time out and should be sitting just behind a horse like First Mission in the fourth or fifth position. That is where Disarm likes to run and he will get a jump on a horse like Red Route One who will be coming from the very back of the field. If you can get 10/1 on Disarm, then he makes some sense as an alternative to two short-priced favorites, but I would hate taking less than 6/1 on a horse that has not won off Lasix in nearly two years.

#8 Red Route One (15/1) – Everyone’s favorite closer, another son of Gun Runner trained by Steve Asmussen romped to victory last time out in the Essex (G3) where he got strong fractions to run at, which has always been the key with this late-charging horse. It was promising to see him return to form as he had fallen off in recent starts since winning the Cornhusker (G3) last year at Prairie Meadows. Historically, he has run well at Oaklawn Park hitting the board in five of eight career starts with two wins, so he can handle the track. It is interesting that Asmussen’s son, Keith, opted to ride Disarm rather than stay on Red Route One, which means Asmussen’s other son, Erik, takes over the mount for Saturday. Despite a relatively short field, you can still expect Red Route One to likely be double-digit lengths back at the half-mile mark as he does all his running in the late. The track configuration for running 1 1/8 miles at Oaklawn Park is ideal for him as he does not have to contend with a short stretch, which gives Erik Asmussen some flexibility regarding whether he makes the Oaklawn Middle Move to get him into contention prior to the second turn or whether he makes his move a bit later. His return to form last time out might be a blip on the radar, but it might also speak of things to come, which means that his 15/1 morning line odds are very enticing for a horse coming off a graded stakes win over the track. Finally, note his 7-10 record hitting the board at the nine furlong distance where he has five wins.