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Oaklawn Handicap: Last Samurai Rates Top Billing Among a Classy Field of Seven Older Males

Written by: Brian Zipse
Published April 19, 2023
15 min read

Oaklawn Handicap Odds and Post Position

Check out our predictions and odds for the Oaklawn Handicap at Oaklawn Park!










D Cabrera

M Villafranco





C Torres

D W Lukas





K Desormeaux

E Moger Jr





J Rosario

M Stidham





R Santana Jr

T Fincher





F Arrieta

K McPeek





L Saez

T Pletcher

*Odds provided by author Brian Zipse.

Oaklawn Handicap Predictions and Best Bets

Here are my plays ($60 in total)

$20 Win - Senor Buscador = $20

$10 Exacta Box - Senor Buscador and Last Samurai = $20 

$10 Exacta Box - Senor Buscador and Stilleto Boy = $20 

If you're playing only to win, go with my top pick Senor Buscador (12/1).



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Oaklawn Handicap Predictions

In search of a graded stakes hat trick at Oaklawn Park, Last Samurai rates top billing among a classy field of seven older males in Saturday’s $1 million Oaklawn Handicap.

A chestnut son of Malibu Moon trained by the venerable D. Wayne Lukas, the 5-year-old comes off consecutive strong wins over the track in the Grade 3 Razorback and the Grade 3 Essex.

Vying for favoritism with Last Samurai will be the Todd Pletcher-trained Charge It. A 23-length winner of the Grade 3 Dwyer at Belmont Park last summer, he has returned from a layoff with two solid efforts. 

Most recently second in the Grade 2 Gulfstream Park Mile, the lightly raced 4-year-old was also second in last year’s Grade 1 Florida Derby.

Fresh off an exciting 1-2 finish in the Grade 1 Santa Anita Handicap, Stilleto Boy and Proxy also merit strong consideration on Saturday. 

Stilleto Boy earned his most important career victory last time and was a solid third in the rich Pegasus World Cup before that.

Proxy, beaten just a neck seven weeks ago, earned his first career Grade 1 victory three starts back when he won the Clark Handicap at Churchill Downs in November.

Rounding out the field for the Grade 2 Oaklawn Handicap will be the graded stakes winning trio of Classic Causeway, Senor Buscador, and Rated R Superstar.

Oaklawn Handicap Predictions and Race Analysis

Charge It

An impressive and romping winner of the Dwyer Stakes last summer at Belmont Park, big things have always been expected for this son of Tapit. Trained by Todd Pletcher, he has looked like a horse destined to become a Grade 1 winner since beginning his career early last year. 

It hasn’t happened yet, but Saturday could be the start of bigger things. He has enough early speed to challenge for the early lead here, but Classic Causeway and Stilleto Boy might also have a say. 

Coming off a second-place finish in the Gulfstream Park Mile, he will need to take a step forward, but his third race off the layoff should be a good spot to do this. He is an obvious threat, but not quite my top pick.

Last Samurai

An impressive winner of two straight graded stakes, it’s very apparent that this experienced son of Malibu Moon is fond of the Oaklawn Park track. Trained by the legend D. Wayne Lukas, many of his best performances have come over the oval, including this race last year. 

While he hasn’t proven himself as a top older male yet elsewhere, this could be the year where he takes things to a higher level as a mature 5-year-old.

Likely to sit mid-pack early, with a fair amount of speed in front of him, it’s probable that he will once again run another strong race at his favorite track. This will be his toughest test yet, though, as he looks for three straight.


Other than the Grade 1 Clark three races back, this is a horse who often looks good, but seldom finds the winner’s circle. 

He has run plenty of good races, including last out when a closing runner-up in the Grade 1 Santa Anita Handicap, but the 1-for-11 overall record in stakes races is a concern. With that said, he rarely runs a poor race, and this is the same distance where he broke through in the Clark.

A strong early pace, which is possible here, would help his rally, but I am going to side with a couple of horses who can get the jump on him early in this one.



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Stilleto Boy

Much like Proxy, we had been waiting for this consistent son of Shackleford to break through and win something big, and it finally happened last time in the Grade 1 Santa Anita Handicap, winning at odds of 13/1. 

Given a masterful ride by Kent Desormeaux, he pounced at just the right time and was a game-winner of the prestigious race. Before that, he ran well when third in the Grade 1 Pegasus World Cup. 

Now 5, he may be turning a corner and could be ready to move to the top of the division. This will be another big test. If he can get another good trip here, he rates a big chance in this strong field.

Classic Causeway

This Grade 1 winner returned fresh and ready last time in the Essex and was a game second behind Last Samurai. If he can improve upon that effort, he will once again be a real threat here. I’m not so sure it will happen, though. 

In his first race back, he was able to get comfortable in the lead. This time, with horses like Charge It and Stilleto Boy hounding him early, I think it will be much tougher for him to stay strong in the stretch.

 I have plenty of respect for him, as he is a very good horse on both dirt and turf, but this race does not look set up to be his best spot.

Senor Buscador

An impressive winner of the Grade 3 Ack Ack last fall at Churchill Downs, he was unfortunately not able to repeat the effort in the Grade 1 Breeders’ Cup Dirt Mile. 

Now 5, the Todd Fincher-trained son of Mineshaft could be ready to take that next step up. His seasonal debut came in a minor stakes race at Sunland Park, and he won as he should. Now he returns to top-level racing against a strong field. 

Because the two-time stakes winner is among the least accomplished in the field, we should get very nice odds as the likely sixth choice. I like his chances to run big from mid-pack here and I am going to pick him to pull off the upset. He is the top pick.

Rated R Superstar

A five-time winner at Oaklawn Park, this old pro will be looking to prove he still has the goods at the ripe old age of 10. 

While winning another stakes race this year would come as no surprise, it’s hard to believe that it will happen on Saturday. His recent races, where he has been well beaten by Last Samurai, just do not stack up well against the other six classy horses in the field.

Likely to be last early, the winner of nearly $2 million lifetimes seems very unlikely to pass many of these down the stretch.



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How to Watch the Oaklawn Handicap

Oaklawn Handicap Race Information

  • What: Oaklawn Handicap (Grade 2)

  • Location: Oaklawn Park

  • Time: Saturday, April 22 -- 6:06 pm Eastern time

  • How to Watch: FanDuel TV

  • Purse: $1,000,000

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Image for Brian Zipse


Brian Zipse

293 Articles

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]

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