Preakness Stakes Betting Odds, Preview, Picks: Best Bets to Win, Longshots & Undercard Wagers (Saturday, May 15)

The days leading up to the second jewel of horse racing's Triple Crown have not been without drama.

The 2021 Preakness Stakes will take place Saturday, with a post time scheduled for 6:47 p.m. ET, and will feature 10 3-year-old horses running 1 3/16 miles over the iconic main track at Pimlico Race Course in Baltimore. The race will air live on NBC.

Medina Spirit was tabbed the morning-line favorite earlier in the week after drawing the No. 3 post position. The Kentucky Derby winner opened at 9-5 odds, but has since fallen to the second choice at 3-1 odds behind new favorite Midnight Bourbon at 5-2 odds. Concert Tour is the third choice at 4-1 odds.

Our horse-racing experts have detailed their favorite win bets, plus they agree on the same horse as their top longshots for the 146th running of the race. They have also included their favorite bet on the undercard, which is loaded with stakes races.

How you use the longshots (if at all) is up to you. Maybe you’re feeling froggy and want to put a few bucks on them to pull the upset. Or perhaps you go the safer route and play them underneath one of your interesting exotic wagers.

That said, let's jump in:

Best Bet to Win the Preakness Stakes

Mike Conti

No. 10 Concert Tour (4-1)

The other Bob Baffert horse would have rivaled Essential Quality for favoritism in the Kentucky Derby before he ran a disappointing third in the Arkansas Derby. He was then held out of the Kentucky Derby and pointed toward this race.

Prior to that lackluster effort, No. 10 Concert Tour was undefeated and won the Grade 2 Rebel geared down in an impressive victory. He looks to be faster, but it will be interesting to see which Baffert charge has the lead out of the gate.

Concert Tour gets Hall of Fame jockey Mike Smith in the irons and his outside post should allow him to get the positioning he would like.

Jeremy Pond

No. 5 Midnight Bourbon (5-2)

Flashback to August of 2015 at Saratoga Casino and race track in upstate New York. I had rented a house on Saratoga Lake for the racing summer season at Saratoga Race Course, home to one of the most iconic tracks in North America.

We had just sat down among the general-admission crew to catch some harness racing when I noticed a surprising face sitting next to us on the bench directly across from the finish line. It was none other than trainer Steve Asmussen, who has No. 5 Midnight Bourbon entered in the Preakness Stakes.

Asmussen, who was in town with jockey Rosie Napravnik to run standout filly Untapable in the Shuvee Handicap at The Spa (she finished second to Stopchargingmaria), just blended in with the common men and women there enjoying the races. Having grown up in the sport, so many horsemen/horsewomen aka the trainers are the blue-collar type. The majority aren't wearing tinted glasses and Armani suits.

Asmussen looks and acts like a guy who has dedicated his life to the sport. He comes off like the kind of trainer who cares as much about a $16,000 maiden claimer in his barn as he does his top horses like Midnight Bourbon or the two Preakness winners — the mighty Curlin and spectacular filly Rachel Alexandra — he led to victory in the run for the Black-eyed Susans.

I've always hoped he'd win another Preakness after sending out those monsters he had in the late 2000s. Needless to say, I think he's got the next champion in the son of Tiznow, who just happens to be my favorite sire.

Midnight Bourbon had a horrific start in the Kentucky Derby, getting bounced around 50 yards out of the starting gate and shuffled back to 12th place heading into the clubhouse turn. The brutal beginning effectively ended any chances of him winning, but he picked off numerous tired horses down the stretch to finish a respectable sixth in the 20-horse field.

With a better start, I think Midnight Bourbon — as well as Rock Your World –would have been right in the mix early on and who knows what would have happened if things went in a different direction. Asmussen's contender looked solid finishing second to Hot Rod Charlie in the Louisiana Derby before that, so I fully expect a big effort from him in this intriguing race.

Asmussen made a huge jockey switch on Midnight Bourbon as well, replacing Mike Smith with reigning three-time Eclipse Award winner Irad Ortiz Jr. for this 1 3/16-mile affair.

Ortiz is more aggressive rider than Smith, so I fully expect him to have Midnight Bourbon on or no less than a half length off assumed front runners Medina Spirit and Concert Tour.

If Ortiz gets the lead, don't expect Medina Spirit to get past him either. Despite what some of you might want us to believe, Bob Baffert's Kentucky Derby winner can't — and doesn't want — to pass horses. His efforts in the Santa Anita Derby, San Felipe Stakes and Sham Stakes prove that point. Go watch the replays.

Midnight Bourbon opened at 5-1 odds on the morning line, but has since been bet down to the favorite at 5-2 odds at the time this story was published. My guess is we'll see his odds tick back up as more money comes in, but don't expect anything north of 4-1 odds when they hit the gate.

That said, I'm fading both Baffert horses. If they beat me, so be it. However, I'm hoping both run as well as Baffert trainee Beautiful Gift did in Friday's Black-Eyed Susan Stakes at Pimlico. Beautiful Gift, who was the favorite in the race, was never in contention and finished well back in seventh place.

Sean Zerillo

No. 10 Concert Tour (4-1)

I hate to give out a Baffert horse here after his tainted Kentucky Derby winner cost me a five-figure payday by way of Mandaloun, but No. 10 Concert Tour is both the likely winner and the best value bet on the Preakness board.

Concert Tour, who was one of the best workers at Churchill Downs in the week leading up to the Kentucky Derby, looks primed to bounce back after a relatively poor effort in the Arkansas Derby on April 10. His win in the Rebel Stakes on March 13 was considered one of the best runs of the entire prep season, though he didn’t beat much in that field.

Concert Tour should be able to work out a good stalking trip behind his stablemate Medina Spirit, and I think he’ll have more left in the tank when the two turn for home.

Best Preakness Stakes Longshots

Mike Conti

No. 4 Crowded Trade (7-1)

Back in 2017, Cloud Computing won the Preakness for trainer Chad Brown. If you look at the past performances for that winner four years ago coming into that race and the past performances from No. 4 Crowded Trade, there’s not much difference.

Crowded Trade, also trained by Brown, and earned a third-place finish last time out in the Wood Memorial. He has a closing kick, but doesn’t have to be too far off. Crowded Trade will be able to sit back behind Medina Spirit, Concert Tour and Midnight Bourbon and pounce late.

He’s a long shot that’s a must use underneath in your vertical wagers.

Jeremy Pond

No. 4 Crowded Trade (7-1)

You could give me a dart to throw at a board featuring paper tags with the name of every horse that's not Medina Spirit, Concert Tour or Midnight Bourbon and they'd all be legit longshot plays in this race.

The reason why picking one Preakness entrant is so difficult is due to the fact there are several options in a race loaded with a million questions.

That said, I've landed on No. 4 Crowded Trade as my pick among the group. Trainer Chad Brown will send out the son of More Than Ready after his layoff following a third-place finish in the Grade 1 Wood Memorial at Belmont Park.

It was a smart move by Brown after his charge put together a solid effort in the Wood Memorial — a race that completely fell apart late — and resulted in 72-1 longshot and Kentucky Derby entrant Bourbonic to earn the victory.

What drew me to Crowded Trade is the eerily similar path the connections have taken when compared to 2017 Preakness winner Cloud Computing. That Brown horse, who also had Hall of Fame jockey Javier Castellano aboard, had just three starts prior to taking the second jewel of horse racing's Triple Crown.

Crowded Trade, who has a second and third in his two stakes tries in three starts, also has the same record Cloud Computing boasted prior to his 13-1 upset win at Pimlico.

I think we'll probably get similar odds to what's currently on the board, but if you're really set on this horse I would jump on his via a futures wager in case his number ticks down even more prior to the race.

Sean Zerillo

No. 4 Crowded Trade (7-1) — win contender | No. 2 Keepmeinmind (10-1) — use in all exotic wagers

I really like No. 4 Crowded Trade as a longshot win contender,  but my favorite longshot to use underneath in exotics is No. 2 Keepmeinmind. He was last early in the Kentucky Derby — and 19 lengths behind the leader at the second call — but was one of the few running late and passing tired horses down the stretch.

Keepmeinmind was better as a 2-year-old, but might have done his best running of his 3-year-old season in the final few furlongs two weeks ago. And the fact his connections are bringing him back after a seventh-place finish, as one of three Derby horses in this 10-horse field, is a promising sign.

Keepmeinmind is a one-run closer without much chance to win the race unless there’s a supersonic pace, but I do think he can get into the trifecta at a price.

Best Undercard Bets

Mike Conti

Race 12: The Dinner Party Stakes — No. 5 Sacred Life (7-5)

Sacred Life is my best bet of the day.

He finished third last time out in the Grade 1 Makers Mark Mile over a good turf course at Keeneland, where he didn’t switch leads. He will get a firm turf course and trainer Chad Brown is an incredible 32% second off the layoff.

No. 1 Somelikeithotbrown (4-1) will be his target in here and I would have been more worried about Somelikeithotbrown going gate to wire if they hadn’t moved the rail out from 5 feet to 10 feet on Friday at Pimlico.

Sacred Life has two wins and three seconds from five career starts going the mile distance over the turf course. Overall, she has racked up six wins, six seconds and a third from 17 races on the grass.

She’s not only my best bet of the day, but one to single in all multi-race wagers.

Jeremy Pond

Race 10 — Jim McKay Turf Sprint Stakes

Bet: $4 Exacta box — No. 4 The Critical Way (5-2) | No. 5 Hollis (6-1) | No. 11 Firecrow (10-1) | No. 13 Completed Pass (7-2)

This is the arguably the deepest field on the 14-race card, with several horses with a shot to win this stakes race named in honor of the legendary ABC sports broadcaster.

If you asked me to pick a winner, I would lean toward No. 5 Hollis for two reasons. The first is the fact the 7-year-old gelding by Kentucky Derby winner Street Sense is the defending champion in this five-furlong sprint on the turf. The second is that he's already beaten No. 13 Completed Pass in this race, holding off the 7-year-old son of Pass Rush down the stretch to get the victory.

Yet, despite my affinity for Hollis and the fact he gets jockey Irad Ortiz Jr. in the saddle, I'm going to use both horses in an exacta box with favorite No. 4 Critical Way and longshot No. 11 Firecrow in this exotic wager.

I like the fact I have the favorites paired with Hollis and Firecrow, who will have one of the world's best riders in Joel Rosario aboard. It wouldn't shock me if this pair pulled off the upset, so I'm happy to use the two betting favorites along with a couple of other top contenders at nice prices.

Sean Zerillo

Race No. 3 — Chick Lang Stakes

Bet: Exacta box — No. 2 Mighty Mischief (5-2) | No. 4 Jaxxon Traveler (4-5)

This six-furlong dirt sprint is typically one of my favorite races on Preakness day and has unveiled superstars in past runnings like trainer Steve Asmussen standout Mitole back in 2018.

Asmussen has the top two selections in this year's edition of the Chick Lang, and the No. 2 Mighty Mischief and No. 4 Jaxxon Traveler are my top two win contenders by a fairly significant margin.

I’m pairing both of his charges together in an exacta box. We'll hope Mighty Mischief can get the best of his stablemate for a larger payday.