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Harlan’s Holiday Stakes (Gulfstream Park) Predictions: Simplification Looks to Be the Pair’s Top Rival

Written by: Brian Zipse
Updated December 28, 2022
15 min read

Harlan’s Holiday Stakes Odds and Post Position

Check out our predictions and odds for Harlan’s Holiday Stakes at Gulfstream Park!










E Zayas

S Joseph Jr





L Saez

T Pletcher





J Ruiz

J O’Dwyer





J Alvarado

A Sano





J Rosario

W Mott





L Reyes

M Williams





I Ortiz Jr

S Joseph Jr





T Gaffalione

J Alvarado

*Odds provided by author Brian Zipse.

Harlan’s Holiday Stakes Predictions and Best Bets

Here are my plays ($50 in total)

$20 Win - Simplification = $20

$10 Exacta Box - Simplification and O’Connor = $20 

$5 Exacta Box - Simplification and Pioneer of Medina = $10

If you're playing only to win, go with my top pick Simplification (5/1).    



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Harlan Holiday Stakes Predictions

A field of eight, led by the Saffie Joseph Jr.-trained pair of O’Connor and Skippylongstocking, are set to do battle in Saturday’s Grade 3 Harlan’s Holiday at Gulfstream Park

The morning line favorite in the 1 1/16-mile test, prep for next month’s $3 million Pegasus World Cup, is O’Connor.

A Group 1 winner in Chile, the import was impressive in his U.S. debut, winning a Gulfstream Park allowance race by six lengths back in October. 

Skippylongstocking, meanwhile, was freshened after a disappointing ninth-place finish in the Grade 1 Pennsylvania Derby. 

Before that, though, the Exaggerator colt had rattled off several good races, including a third in the Grade 1 Belmont Stakes and a win in the Grade 3 West Virginia Derby. 

Simplification looks to be the pair’s top rival. He returns to Gulfstream Park where he  won both the Mucho Macho Man Stakes and the Grade 2 Fountain of Youth early this year. 

Most recently the son of Not This Time finished a troubled seventh in the Grade 1 Breeders’ Cup Dirt Mile for trainer Antonio Sano.

Harlan’s Holiday Stakes Predictions and Race Analysis


It looks like the first of two from the barn of Saffie Joseph, Jr. will be a hot favorite as he makes his first stakes start in the U.S. A very successful runner in his native Chile, he came with a big rush to win going away in an allowance race at Gulfstream in his American debut. 

Given plenty of time between races, all eyes will be on the South American to see if he can build upon that eye-catching victory in mid-October.

It certainly would come as no surprise if he backed it up with another win, but in a race without much speed and moving up in class, I will take a shot against him as the heavy favorite.


It will be interesting to see if this son of Exaggerator comes back sharp after three months away since a dull effort in the Grade 1 Pennsylvania Derby. If he does return at his best, he becomes a major threat on Saturday. 

Before the disappointing last run, he had run several good races including a third in the Belmont and a win on a sloppy track in the West Virginia Derby. He also has won at Gulfstream Park twice before.

He’s actually run against Simplification several times and split the results, but I think this one may set up a bit better for his rival. Still, he is an obvious contender here.


There is a lot to like about this graded stakes winning son of Not This Time. A two-time stakes winner at Gulfstream Park, six of his last seven races were against Grade 1 competition. This race will clearly offer the Antonio Sano-trained colt some class relief

You have to go back eight races to find his last win, but it was an impressive score in the Grade 2 Fountain of Youth. He’s run well against stiff competition in most of his races since, including a good fourth in the Kentucky Derby. 

I am willing to give him a pass on his seventh-place finish in the Breeders’ Cup Dirt Mile after a rough beginning to the race. Without much speed in this race, I like his chances to be involved every step of the way at his favorite track. He is the top pick.

Pioneer of Medina

The likely fourth choice comes in off a win last time at Churchill Downs, which broke a string of three consecutive poor results. The dull streak began in the Kentucky Derby, where he was overmatched, but before that he had some very solid results on the Derby trail in New Orleans. 

The last one was clearly cheaper competition than this, but hopefully was a sign that he has turned the corner. 

In a race with little early speed, he should have enough tactical speed to be well placed early under rider Luis Saez. I don’t love his chances for the win, but he seems like a must use in the exotics.



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South Bend

Second in this race last year, this experienced son of Algorithms has not found the winner’s circle in more than a year. He’s had some good results over the years, collecting better than $700,000 in purse money, but has often settled for a minor share. 

A horse who likes to come from well back, he has finished in the money four times at Gulfstream in six starts but has yet to win there. His last effort, a narrow miss in a sloppy allowance last month at Churchill Downs was solid.

Trained by Bill Mott and ridden by Joel Rosario, he’s certainly eligible to rally up into the exotics, but without much early pace in the race, I like others better.


Trained by Juan Alvarado, this 3-year-old Florida-bred has run 15 of his 16 career races at Gulfstream Park, where he has won four times. 

He can be a little in and out overall, but his last race was solid, losing by just a half-length to the promising import Super Corinto. 

The son of Brethren has yet to do well in a field of this quality, but if he can reproduce the efforts of two of his last three, he is in with at least a fighting chance to run a strong race with attractive odds.

Strike Hard

Three times a winner at Gulfstream Park, this son of Flashback still needs to prove he can compete well with graded stakes company. 

His last win came locally in an allowance race in May, but in seven stakes attempts that sandwich that win, he only has a pair of seconds in which he never threatened the winners. 

If he does eventually break through in a stakes race there is a good chance he does it at Gulfstream, where all of his career victories have come, but this spot looks a little tougher than he really wants.

Cooke Creek

This son of Uncle Mo looked like an up-and-comer last year at 2 when he won his first two races and finished second in the Grade 3 Nashua Stakes. 

Unfortunately, he has not lived up to the promise this year with no wins in four starts. He was keeping good company but was unable to do anything in the last three, before going on the shelf. 

This will be his first start back in more than six months and only a complete form reversal would give him any shot against this field.



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How to Watch the Harlan’s Holiday Stakes

Harlan’s Holiday Stakes Race Information

  • What: Harlan’s Holiday Stakes (Grade 3)

  • Location: Gulfstream Park

  • Time: Saturday, December 31 -- 4:40 pm Eastern time

  • How to Watch: FanDuel TV

  • Purse: $150,000

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Image for Brian Zipse


Brian Zipse

294 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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