Jackson Holland is an experienced sports writer and handicapper based in Pennsylvania. He worked part-time at a racetrack and casino while majoring in English Literature at college, and that inspired a passion for gambling. Holland spent a decade as a journalist working for a variety of regional newspapers before joining the sports betting industry. He writes long-form betting guides for Basketball Insiders, Augusta Free Press and various other publications.
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Following his graduation with an Honors in Business Administration, Nick redirected his focus from conventional stocks and bonds to the world of sports team performance investments. He employs a unique blend of advanced statistics and historical data to construct intricate sports investment models, pinpointing value opportunities and consistently yielding profits. Nick's contributions extend beyond a single platform, as his work can be discovered on outlets such as Pistons Powered, Winners And Whiners, and numerous other publications.
All posts by Nick RaffoulAn elite field will gather at Pimlico Race Course in Baltimore to contest the 2023 Preakness Stakes on May 20. It is one of the biggest races of the year, so horseplayers are on the hunt for Preakness Stakes picks.
This guide will offer top Preakness picks by experts. We have provided our top picks for the win, the place, the show, and exotics such as the exacta and trifecta. You can also compare Preakness odds from the best online racebooks and glean tips on how to successfully bet on the Preakness Stakes.
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2023 Preakness Stakes Favorites
Since it was revealed that Kentucky Derby winner Mage will bid for the Triple Crown, the Preakness Stakes odds reflect his chances of doing that. Challenging the favorite, however, is First Mission who has been saved for this race instead of going to Churchill Downs. These are the contenders for Preakness Stakes glory:
All prices correct as of 11:00 EDT on Thursday, May 11 2023 but subject to change.Preakness Stakes Horses BetUS Bovada Sportsbetting.ag BetOnline MyBookie Mage +175 +175 +185 +185 +137 First Mission +225 +200 +240 +240 +225 Two Phil’s N/A +400 N/A N/A +400 National Treasure +800 +650 +1000 +1000 +1000 Derma Sotogake N/A N/A N/A N/A +800 Tapit Trice N/A N/A N/A N/A +800 Disarm +850 +1000 +750 +750 +800 Blazing Sevens +1100 +1000 +1200 +1200 +1400 Confidence Game +1100 +1000 +1200 +1200 +1600 Red Route One +1400 +1200 +1600 +1600 +2000 Perform +1500 N/A +1600 +1600 +1000 Henry Q N/A +1600 N/A N/A N/A Instant Coffee N/A +2500 N/A N/A N/A Chase The Chaos +3500 +2500 +5000 +5000 +6600 Il Miracolo N/A +5000 N/A N/A +6600 Basketball Insiders’ Preakness Stakes Expert Picks
Once you’ve got to grips with the odds and learned how to bet the Preakness Stakes, it’s time to throw your hat into the ring and back a winning horse. To assist, we have analyzed every contender’s strengths and weaknesses in great detail. These are our Preakness Stakes expert picks:
Our Preakness Stakes Pick to Win
While Mage probably deserves his status favorite to win the Preakness Stakes after that Kentucky Derby victory, there is a case to be made against him. There is just two weeks between Churchill Downs and this second leg of the Triple Crown at Pimlico. That will test the horse’s constitution.
It may instead pay to side with the horse that powerful global operation Godolphin decided to lay out for the Preakness in First Mission. If the owner-breeders and trainer Brad Cox really wanted, they could’ve gone to the Kentucky Derby with him but they took a different approach.
They say patience is a virtue and that may prove the case with First Mission. He’s coming to the Preakness with an under-the-radar prep, but oddsmakers clearly respect him. Put in the futures betting as the main challenger to Mage, the Street Sense colt has plenty to offer and further progress in him now tackling longer than an extended mile for the first time.
Our top pick:
- First Mission to win the Preakness Stakes @ +240
- A $10 bet returns $34 with $24 in winnings
Top 3 Preakness Picks
Nobody betting on the Preakness Stakes should ignore the Kentucky Derby form, however, and one that caught the eye was the fourth home, Disarm. Steven Asmussen knows what it takes to trainer winners of Triple Crown races.
He saddled both Curlin and Rachel Alexandra, a rare successful filly, to Preakness Stakes glory in 2007 and 2009 respectively. In Disarm, he has a Gun Runner colt that ties the form lines of the first two in this year’s betting together.
Although at first glance, Disarm has something to find with them both a replay of his passage through the Kentucky Derby shows he had to switch out at an important stage of the race as there was no way through. He could’ve finished close and certainly in the show.
The other obvious option is Mage himself. He took his form to a new level with Kentucky Derby success, but appeared to win the race by staying. Going back in trip will not automatically suit him. Connections of Mage have every right to chase the dream of a Triple Crown, but he may be vulnerable to fresher horses that haven’t had a hard race recently.
Our picks:
- Mage to place in the Preakness Stakes
- Disarm to show in the Preakness Stakes
Preakness Longshot Picks
The most interesting longshot among Preakness Stakes picks this year is Red Route One. Bettors will have to be of a forgiving nature to get behind him as Asmussen’s other contender totally blew his chance in the Arkansas Derby when dwelling out of the gates.
If he jumps off on terms with the others at Pimlico, however, previous efforts from Red Route One suggest he could have a say in the finish and make the show, or at least outstrip his odds. His length second in the Rebel Stakes, also at Oaklawn Park, earlier in the year behind Confidence Game is a fairer assessment of his ability.
That one seemed to run out of gas when fading in the Kentucky Derby, but the Preakness is a shorter distance and less demanding with fewer runners. If reproducing his penultimate run, then Confidence Game is another longshot that could go well.
Our picks:
- Confidence Game to win the Preakness Stakes @ +1600 with MyBookie
- Red Route One to win the Preakness Stakes @ +2000 wit MyBookie
Preakness Stakes Exotic Picks
The Preakness Stakes is one of the most important horse racing events of the season, and exotic bets are always popular. These are our top Preakness picks in the exotics category:
Preakness Stakes 2023 Exacta Picks
Based on the above tips, our exacta pick is First Mission to beat the favorite Mage. That longer break between races really could be the difference between winning and losing.
Our picks:
- 1st: First Mission
- 2nd: Mage
The payout for the exacta will be revealed after the race. Back in 2021, a $2 exacta on the Preakness paid $98.60.
Preakness Stakes 2023 Trifecta Picks
Joining First Mission and Mage for the trifecta in our Preakness 2023 picks is Disarm. He really did look so unlucky when finding trouble in-running in the Kentucky Derby, so the smaller field should provide better opportunities.
Our picks:
- 1st: First Mission
- 2nd: Mage
- 3rd: Disarm
Back in 2021, a $1 trifecta on the Preakness paid $162.70.
Preakness Stakes 2023 Superfecta Picks
Red Route One can show his true colors at Pimlico and put his Arkansas Derby disappointment well behind him. Our expert feel one of the longshot Preakness Stakes picks can get minor honors and fourth place behind the three selections for the Trifecta.
Our picks:
- 1st: First Mission
- 2nd: Mage
- 3rd: Disarm
- 4th: Red Route One
The $1 superfecta on the Preakness Stakes 2021 paid $1,025.50.
Preakness Stakes 2023 Super Hi-Five Picks
Completing the exotics bets is the ultimate test for bettors. If you can get the first five horses home in the same race, then you should probably join our experts. They’ve gone for National Treasure to round off the Super Hi-Five and follow in the quartet chosen in the above Superfecta.
Our picks:
- 1st: First Mission
- 2nd: Mage
- 3rd: Disarm
- 4th: Red Route One
- 5th: National Treasure
A $1 Super Hi-Five on the Preakness Stakes of 2021 paid $4,857.
Our Top 3 Picks for the Preakness Stakes
Let’s recap our top Preakness picks for 2023 so you’re in doubt what the best bets are:
Pick 1: First Mission to Win the Preakness Stakes
It is hard to look past the first two in the betting on sportsbooks and racebooks for the winner here. Heading up our Preakness best picks is First Mission as he’s had more of a break between runs.
Pick 2: First Mission & Mage Preakness Stakes Quinella
A Quinella, that’s any order Exacta where the unit stake gambled doubles, looks a great idea with the two at the head of the Preakness futures betting this year. Whether Mage can suck it up and defy the quick turnaround from the Kentucky Derby remains to be seen. If he can’t, then First Mission is definitely the improving type who can capitalize.
Pick 3: Disarm to Show in the Preakness Stakes
With a bit of luck, Disarm can enjoy a trouble-free trip through the Preakness Stakes and make the show. He was unfortunate to only be fourth in the Kentucky Derby, and it’d be no surprise if he betters that finishing position at Pimlico.
Best Preakness Stakes Betting Sites
We have reviewed the major sites offering Preakness Stakes odds in detail. We focused on the quality of the fixed odds, the bonuses, payout speeds, and much more. These are the best Preakness Stakes betting sites in 2025:
5 Key Preakness Stakes Trends That Can Help You Pick the Winner
Now that you know our Preakness Stakes picks for this year’s big race and our top places to wager, we also asked expert handicappers to study the key stats and trends. While there are no guarantees that these will pinpoint the winner, they will help you make more astute wagering decisions. These are our top 5 key Preakness Stakes trends:
1. New Shooters Grow in Prominence
Twenty-one of the 22 Preakness Stakes winners from 1984 to 2005 had taken part in the Kentucky Derby. The only exception was the 2000 winner Red Bullet. However, from 2006 onwards, horses that did not contest the Derby – known as new shooters – have enjoyed a lot more success.
Bernardini (2006), Rachel Alexandra (2009), Cloud Computing (2017), Swiss Skydiver (2020), and Rombauer (2021) did not compete in the Kentucky Derby, but they did win the Preakness Stakes.
However, Rachel Alexandra and Swiss Skydiver prepped in the Kentucky Oaks, and 17 of the last 21 winners, therefore, came from the Derby or the Oaks. The only exceptions were Bernardini, Cloud Computing, and last year’s winner, Rombauer.
2. Inside Post Positions are Advantageous
Six of the last nine Preakness Stakes winners came from the first half of the field, so the inside post positions are coveted. It will be important to look for the barrier draw when making your final Preakness picks.
Two of the last nine winners broke from the rail – War of Will and American Pharaoh. War of Will raced on the inside for most of the Preakness Stakes en route to victory in 2019. Exaggerator, Cloud Computing, and Swiss Skydiver all stuck to the inside too, showing that it pays to save ground on the tight Pimlico track, with its tough turns.
3. Late Closers Have Struggled
This is a race dominated by pacesetters and speed horses. Four of the last 15 Preakness Stakes winners led from wire to wire – Justify, American Pharaoh, Oxbow, and Rachel Alexandra. A further six of the last 15 winners were within 3 1/2 lengths of the lead after half a mile.
Tactical speed is important. Swiss Skydiver, War of Will, Cloud Computing, California Chrome, I’ll Have Another, and Shackleford – all winners since 2011 – used pace-tracking tactics during the race.
Late closers struggle to win this race. Exaggerator, the 2016 victor, was an exception, but he relished the unusually sloppy conditions that year. Rombauer in 2021 and Curlin in 2007 also buck the trend, but in general, pace matters.
4. Double-Digit Winners are Reasonably Common
This table shows the past 10 Preakness Stakes winners, along with the fixed odds available on them.
Year Winning Horse Jockey Trainer Odds 2022 Early Voting Jose Ortiz Chad Brown 57/10 2021 Rombauer Flavien Prat Michael W. McCarthy 118/10 2020 Swiss Skydiver Rory Albarado Kenneth McPeek 117/10 2019 War of Will Tyler Gaffalione Mark E. Casse 61/10 2018 Justify Mike Smith Bob Baffert 2/5F 2017 Cloud Computing Javier Castellano Chad Brown 134/10 2016 Exaggerator Kent Desormeaux J. Keith Desormeaux 13/5 2015 American Pharaoh Victor Espinoza Bob Baffert 9/10F 2014 California Chrome Victor Espinoza Art Sherman 1/2F 2013 Oxbow Gary Stevens D. Wayne Lukas 154/10 2012 I’ll Have Another Mario Gutierrez Doug O’Neill 5/2 As you can see, double-digit winners – horses priced at 10/1 (+1000) or greater – have performed well. They won two of the last four Preakness Stakes, and three of the last six. Justify American Pharaoh and California Chrome stand out, but they were all dominant Kentucky Derby winners, so do not write off mid-range horses in the betting.
5. Look Out for Proven Stakes Winners
Twenty-three of the last 26 Preakness Stakes winners had previously won a graded stakes race. Seventeen of them had at least one Grade 1 win under their belts before lining up at Pimlico.
The three exceptions to the rule were Shackleford (2011), Cloud Computing (2017), and Rombauer (2021). However, it is worth noting that each of them had finished second in Grade 1 races. Shakleford was narrowly beaten in the Grade 1 Florida Derby, and Rombauer was runner-up in the Grade 1 American Pharoah Stakes before winning the Preakness.
What are Preakness Stakes Picks?
Preakness Stakes picks are predictions on how this race will unfold. Handicappers study the past performances of each runner in exhaustive detail. They focus on how well a horse has reacted to certain conditions, the distances it favors, and how strong it has been in races of a similar caliber.
Handicappers picks for the Preakness also factor in issues like fatigue and momentum. If a horse appears to be on an upward curve, it could be an interesting option. They must also check the weather forecast and consider the expected conditions at Pimlico. For example, it was sloppy in 2016, and Exaggerator relished those conditions.
The idea is to ultimately rank each horse in order, focusing on attributes such as speed, style, and endurance. You can rule certain horses out, and at the end of the process, you are left with an idea of which horse will win.
Preakness expert picks are then released. Some are free, while certain handicappers sell their Preakness Stakes picks.
Where to Find Preakness Stakes Expert Picks
We have provided our Preakness top picks on this page, but we also encourage you to gather as much information as possible before betting on this race. As such, it is worth checking out some additional Preakness Stakes picks from respected handicappers.
One interesting resource is Preakness Stakes picks from TVG, which offers live streaming of the big race. There is no official Preakness Stakes site, but the experts at the Kentucky Derby site often give out Preakness picks. You can also scour social media but stick to handicappers with proven records.
How to Make Preakness Stakes Picks and Predictions
If you would like to handicap this race and come up with your own Preakness picks, there are some attributes that you should consider:
- Speed Figures: Pace is an important trait for Preakness winners. We have seen a few gate-to-wire winners, while most recent victors have displayed tactical speed. Epicenter earned a 120 Timeform Speed Figure at the Kentucky Derby, compared to 116 for Secret Oath at the Oaks.
- Class: You should factor in the quality of the opposition that each horse has beaten this year. Runners that performed well in major Grade 1 races such as the Kentucky Derby, Kentucky Oaks, and Florida Derby should relish the Preakness.
- Post Positions: Horses drawn on the inside post positions tend to perform well at the Preakness, as Pimlico is notorious for its tight corners. Check the barrier draw before making your final Preakness Stakes picks.
- Pace and Style: Look out for pacesetters and speed horses, who have a great record in this race. It is rare to see a closer win the Preakness.
- Staying Power: Staying power is important, but not quite as important as the Kentucky Derby, as the Preakness is a little shorter. Horses that looked to be running out of steam towards the end of the Derby could enjoy a slightly shorter distance.
We would also encourage you to take advantage of as many horse racing free bets as possible before the race begins. Online racebooks give out free bets to new and existing customers to stand out from rival sites.
Picks and Parlays for the Preakness Stakes
A parlay involves combining a bet on the winner of the Preakness Stakes with a bet on the winner of another race for a single wager. The most common option is a double featuring the Preakness Stakes and the Black-Eyed Susan, which is run the previous day at Pimlico. Some racebooks will allow you to parlay the Preakness with additional events.
More on horse racing betting…
If you would like to learn more about betting on the Preakness Stakes, check out the additional resources on these pages:
- Best Preakness Stakes betting sites – Find the best online betting sites for betting on the Preakness Stakes
- Preakness Stakes odds – Compare and learn to read the odds from leading Preakness Stakes racebooks
- How to bet on the Preakness Stakes – A detailed breakdown of every betting option on the Preakness Stakes
- Best racebooks – A guide to the best racebooks for US and international racing throughout the year
- Parimutuel betting – Learn how most horse racing bets are calculated
- Pool betting – An overview of the pool system used to calculate your profits from successful racebook wagers
- Virtual horse racing – A guide to betting on virtual races controlled by Random Number Generator software
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