Sleeper Picks for the 2021 Preakness Stakes

| May 12, 2021 10:31 am PDT

Like most people, I expected the favored Essential Quality to win the 2021 Kentucky Derby. There is always merit in considering horse racing sleepers, though, which is why I pointed out my favorite value bets before that race.

One of them – Medina Spirit – came in with nice +1400 odds and managed to stage the upset.

Bob Baffert’s trainee was later under the microscope due to a potential cheating scandal, but hey, a win is a win.

In all seriousness, the main point here is that anyone looking to bet on the 2021 Preakness Stakes should take a similar approach; at least glance at value picks that can win this thing.

Medina Spirit made my list last week, and I’m ready to hand out my favorite sleeper picks for the 2021 Preakness Stakes, as well.

The Kentucky Derby winner enters a 10-horse field as the favorite with +175 odds at the top horse racing betting websites, but could bettors get more bang for their buck elsewhere?

It’s certainly possible, and these 2021 Preakness Stakes sleepers just might be the horses to turn to.

Crowded Trade (+1200)

For me, the Preakness Stakes sleeper conversation really only starts with horses priced at +1000 and beyond. To be frank, that’s probably the case with any race when talking about odds and true sleepers.

Regardless of your definition of what makes a sleeper, Crowded Trade is the first one in for me, and if there must be one sleeper pick to target, this is it.

Crowded Trade is both a sleeper and a viable contender, pulling in with the fourth-best 2021 Preakness Stakes odds yet still offering nice value to willing bettors.

Inexperience is the only real drawback here. Crowded Trade has only competed in three events, but he’s won one and never finished worse than third.

His light (but solid) resume includes a second-place finish behind Weyburn at the 2021 Gotham Stakes and a third-place run at the 2021 Wood Memorial Stakes.

Not only has this colt competed well but he’s got a strong trainer in Chad C. Brown. Brown’s lone Triple Crown win on his resume? The 2017 Preakness Stakes.

History doesn’t always repeat itself, but the solid form, pedigree, and value could be enough to convince bettors to back Crowded Trade.

It’s worth noting that Risk Taking (+1200) is another Brown trainee to consider, but a worse showing at the Wood Memorial Stakes has me liking Crowded Trade a bit more.

Keepmeinmind (+2000)

This isn’t my pick to win, but keep in mind that Keepmeinmind (see what I did there?) finished 7th at the 2021 Kentucky Derby.

Despite that solid showing in a packed 20-horse race, he enters with the seventh-best odds for the Preakness Stakes.

Arguably, he should be shown a bit more respect due to that, although most will scoff at less than spectacular finishes at the Blue Grass Stakes and Rebel Stakes.

While that is absolutely a bit concerning, Keepmeinmind rallied after falling behind early and did that against stiff competition. A faster start this weekend could make this horse one of the better 2021 Preakness Stakes sleeper picks.

Unbridled Honor (+2200)

This is just a 10-horse field, so how many 2021 Preakness Stakes sleepers can there possibly be?

I’ll stop the excitement at Unbridled Honor, which has my attention for a few reasons. First, because it’s another talented colt with a famous trainer in Todd Pletcher leading the charge.

Admittedly, this hasn’t been Todd Pletcher’s race. He’s even opted to bypass it at times, and he’s 0-8 in eight attempts at winning it.

Maybe his drought doesn’t end this weekend, but it certainly could. Unbridled Honor has flashed some upside after taking second at the 2021 Lexington Stakes, as well as a respectable fourth-place finish at this year’s Tampa Bay Derby.

The strong showing at the Lexington Strakes was especially encouraging for Pletcher, who had this to say about his surging colt.

“He finished up well, and he continues to improve with each start. He had a good pace to run that day. Hopefully, it will be a contested pace at Pimlico.”

This is clearly a horse that can run with the pack and has displayed an ability to close strong. In a 10-horse field, bettors have to wonder if Pletcher finally has a gem that can help him snag an elusive prize.

Betting on the 2021 Preakness Stakes

In closing, I’ll come away with two thoughts; make sure you find the best 2021 Preakness Stakes betting sites to ensure you get a good price and go heavy on the top contenders.

The reality here – as much as I love the idea of Preakness Stakes sleepers – is that this is a smaller field, and the elite talent is bound to shine.

Maybe that’s the case in any race, but I feel like the two Bob Baffert horses (Medina Spirit and Concert Tour) are appropriately priced as the top two threats to win the Preakness Stakes.

The horse with the third-best odds could possibly be regarded as a sleeper, as Midnight Bourbon comes in at a cool +600 at BetOnline. If you want value, that’s probably the main horse I would be eyeing.

Midnight Bourbon finished 6th at the Kentucky Derby, and it’s honestly quite arguable he was slowed down early by the commotion in such a loaded field.

The field is cut in half this time, and you have a top-6 returnee that had previously never finished worse than third. The Steve Asmussen colt is a real threat here and my favorite pick of the lot for this weekend.

Of course, bettors are still going to be drawn to the Kentucky Derby winner, and you always want to consider the sleeper picks that offer more upside.

Whatever direction you go in, I hope I helped a bit. Be sure to visit the best 2021 Preakness Stakes betting sites before finalizing your bets, as well.

Noah Davis
Noah Davis

Noah Davis is one of the more diverse writers at Like many of his colleagues, he's a huge fan of both football and basketball. But he also writes about box office records, TV show prop bets, DFS, and all kinds of other subjects.

When it comes to the NFL, Noah's favorite team is the Cleveland Browns. He enjoys cheering them on with his wife and daughter.

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