Oaklawn Handicap Picks & Predictions: Can Skippylongstocking Repeat?

by | Last updated Apr 19, 2025 | Horse Betting

Skippylongstocking Seeks Repeat in Stacked Oaklawn Handicap

Oaklawn Handicap (G2) | Oaklawn Park, Race 11 | Saturday, April 19, 2025
Purse: $1,250,000 | Distance: 1 1/8 Miles | Surface: Dirt
Post Time: 6:10 p.m. CT | For Four‑Year‑Olds and Up

Oaklawn Handicap Picks

  • Skippylongstocking
  • First Mission
  • Banishing
  • Alexander Helios

Oaklawn Handicap Longshots

Red Route One, Disarm

Oaklawn Handicap Analysis

Saturday’s Oaklawn Handicap is loaded with speed and runs directly through morning‑line favorite and defending champ Skippylongstocking. The field of eight includes a mixture of class, current form, and rising talent. All eyes will be on how the early pace unfolds and whether it allows the speed to hold or sets up a dramatic stretch rally from the back half of the field. Either way, the setup hints at a genuine test over nine furlongs and a race that may come down to heart and positioning more than raw talent.

Skippylongstocking has already proven himself at Oaklawn and nearly everywhere else, and he’ll love the 1 1/8‑mile distance. The 6‑year‑old boasts more than $3.4 million in earnings and a reputation for showing up wherever he runs. His campaign leading into this race mirrors last year’s, but better. Last year, he was eased in the Pegasus World Cup Invitational at Gulfstream Park (G1) before winning the Challenger Stakes (G3) at Tampa Bay Downs. This year, he finished third in the Pegasus and looked good repeating in the Challenger Stakes (G3) with a big 104 Beyer Speed Figure. He also has tactical speed, which allows him to sit just off the pace in here. If they go too slow early, he can go to the lead anytime, but he’ll likely sit and pounce in late turn, open up in early to mid‑stretch, and try to hold on.

First Mission has been on the radar since early last year and makes his second start of the season after finishing third beaten a neck in the Razorback Handicap. That effort came off a layoff, and he may have been compromised by a possible track bias, according to trainer Brad Cox. Since then, he’s been working steadily and appears poised for a peak effort. With Flavien Prat retaining the mount and a more favorable post draw, he should get a stalking trip behind the early speed. His combination of class and foundation makes him a major threat. He won the Essex Handicap (G3) at Oaklawn Park last year at today’s distance, and his best Beyer Speed Figures make him a legitimate win threat.

Alexander Helios stepped up in the Razorback and passed the test with grit, outdueling fellow Oaklawn Handicap entrants Banishing and First Mission to win the photo by a head. That was his stakes debut, and the 5‑year‑old made it count. He’s now hit the board in 11 straight races and seems to have matured into a reliable performer with tactical speed and determination. As a half‑brother to Preakness winner Rombauer, there’s stamina in his bloodlines, and his recent form suggests he belongs in any serious discussion for the win.

Banishing looked like he might be going the wrong way early last year, but since transferring to the barn of David Jacobson, he’s turned things around in a big way. He nearly won the Razorback, then came back with a strong score in the Oaklawn Mile, showing acceleration and determination in the stretch. His current form is among the best in the field, and with five wins in his last seven races, it’s hard to knock his upward trajectory. He’s battle‑tested and maybe still improving.

Just who will set the pace is a mystery, as First Mission, Skippylongstocking, Alexander Helios, Tarantino, and Banishing all have enough speed to do so if they feel like it. There’s probably a good chance of a contested pace, and it will likely depend on who breaks best. Whoever sits just off the speed will have the advantage turning for home, and positioning and timing will be more important than usual.

If things heat up on the front end, Red Route One could be the horse at a nice morning line of 15‑1. He’s a true deep closer and proved it again last month when he rallied from well off the pace to win the Essex Handicap at this same distance and track. He was also third in this race last year, and when the pace collapses, he’s usually somewhere in the photo. He’ll need a fast setup and a clean trip, but he fits the profile of a horse that can pick up tired runners late.

Disarm, his stablemate from the Steve Asmussen barn is more tactical but still capable of a late punch. He returned from a long break to win an allowance race at Oaklawn and has worked well since. While this is a class hike, his back class, including a fourth‑place finish in the 2023 Kentucky Derby, suggest he has the raw ability to compete here on his best day. He’s a sneaky player if the pace turns chaotic.

Tarantino ran second in the Essex but was never a serious threat to Red Route One. He’s run respectable races at this level, but his ceiling may be a bit lower than what’s required to win this race. He often shows some speed before fading late. Go West Go is making his first start in stakes company and looks overmatched on paper. His best races have come in condition allowance company, and the jump to facing millionaires is steep.

The Oaklawn Handicap is a showdown between established class and rising form, between tactical speed and late‑race power. Skippylongstocking enters as the horse to beat with a proven record and ideal running style, but he’ll have to earn it. First Mission is primed for a big race in his second start off the layoff. Alexander Helios and Banishing bring excellent current form. And if the pace gets hot, Red Route One and Disarm are capable of spoiling the party. In a race where trip, tactics, and timing will decide everything, the winner won’t just need to be fast; they’ll also need to be smart and brave.

If the track is playing fair, Skippylongstocking is the horse to beat. If it’s favoring speed, he’s probably still the horse to beat, although he’ll have a tougher time getting by the speed horses than he did in his last. Red Route One is intriguing at a big price based on the projected pace scenario. On a fair surface, he’s the potential upsetter.

We’ll play Skippylongstocking to win and place and use him first and second in the exactas, trifectas, and superfectas over Red Route One, Disarm, First Mission, Alexander Helios, and Banishing. We’ll include Tarantino in third and fourth on our trifectas and superfectas. We’ll also make a smaller win‑place wager on Red Route One, box him in an additional exacta with Skippy, and wheel him up and down with all in a $1 exacta. Note that if the track is favoring speed, Red Route One’s task becomes much tougher.

Can Red catch Skippy at a price? We hope so!

Suggested Wagers

  • Win/Place: Skippylongstocking
  • Win/Place (smaller): Red Route One
  • Exacta, Trifecta & Superfecta Keys: Skippylongstocking over Red Route One, Disarm, First Mission, Alexander Helios, Banishing
  • Include Tarantino in 3rd/4th slots of TRIs and SUPERs
  • $1 exacta wheel: Red Route One with all

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