Preakness Stakes Expert Predictions and Betting Advice

Bourbon War Odds to Win the 2019 Preakness Stakes with Picks and Predictions
by Trevor Whenham - 5/10/2019

Bourbon War checks a lot of boxes heading into the Preakness this year. He is nicely-bred. He has as good a jockey as any horse could hope for. And he has shown some talent. But what we have not yet seen is an effort that truly shows us that he is a top-level horse. The pieces are there, but the list of horses that have had the pieces and haven't assembled the puzzle is incredibly long. Can Bourbon War be different? Can he win the Preakness?

Anothertwistafate Odds to Win the 2019 Preakness Stakes with Picks and Predictions
by Trevor Whenham - 5/10/2019

Anothertwistafate is a nice enough horse but not one that you would generally pay a ton of attention to during Triple Crown season or the preps that lead to it. But for one big reason, which we'll touch on in a bit, he's a sentimental choice in the Preakness for people, like me, who have an obsession with the Triple Crown that borders on crazy. Can sentimentality come through when it matters in the Preakness this year?

Alwaysmining Odds to Win the 2019 Preakness Stakes with Picks and Predictions
by Trevor Whenham - 5/10/2019

The Federico Tesio Stakes is the local prep race for the Preakness Stakes, though slightly less so since it has moved from Pimlico to Laurel Park in recent years. The winner of the race typically draws a good bit of betting attention from the local crowd in Baltimore. But most of the time the horse is clearly outclassed and doesn't factor into the race in a meaningful way.

2019 Preakness Stakes Trivia Questions and Answers
by Trevor Whenham - 5/10/2019

The Preakness Stakes is, by definition, a Classic. It is also often a classic race, and it has been the sight of some incredible history over the years. It often gets overshadowed by the other two -- the Kentucky Derby is the greatest of all races, and the Belmont is where Triple Crowns are won and lost.

Signalman Odds to Win the 2019 Preakness Stakes with Picks and Predictions
by Trevor Whenham - 5/10/2019

Every fall, people who love the Triple Crown like I do start to sort through the colts out there and figure out which ones are going to be the ones they attach a piece of their heart to heading into the spring and the start of the prep season.

Where to Bet on the Preakness Stakes in 2019
by Trevor Whenham - 5/9/2019

The Preakness is more than a week away, but hopefully by this point we have gotten past all the drama and distraction and we are at the point where we can again focus on the horses that are actually running. There was a lot of change early on, but it feels like we now have a pretty good idea of what the 10- or 11-horse field will look like - and despite lacking the big names that we would hope for, and lacking the Derby winner for the first time since 1996, it is still a solid and interesting field.

How to Place a Bet on the Preakness Stakes in 2019
by Trevor Whenham - 5/9/2019

I've been going to the races for more than 35 years now - I started 10 years before I was born, or at least that's what I would like to believe. From those earliest days when I would make $2 show bets hoping to ride a parlay all day, I have always had the same rule when it comes to betting on the Preakness. No matter what else I think about the race, I always have to have a blind win bet on the Derby winner.

Handicapping the Kentucky Derby Horses in the 2019 Preakness Stakes
by Trevor Whenham - 5/8/2019

It has taken me much longer than usual this year to get to this article because we have been less certain of what is going to happen than we are used to seeing. The Maximum Security disqualification, and the circus that has been left in the wake of it, has caused all sorts of confusion about which Derby horses will move forward to the Preakness.

2019 Preakness Stakes Field: Early Look and Handicapping
by Trevor Whenham - 5/7/2019

As usual, now that 48 hours have passed between the end of the Kentucky Derby and now, we have a pretty good indication of what the Preakness field will look like. Lots will change between now and then, but typically over half of the field that winds up in the starting gate is identified by now. And though this field lacks the rematch that most would like to see - Maximum Security is not being aimed at the Preakness, so he will not get a chance to beat Country House again and for the first time.

Good Magic Odds to Win the 2018 Preakness Stakes with Picks and Predictions
by Trevor Whenham - 5/14/2018

For a while it looked like Justify was going to get a free pass in the Preakness. As time passed, though, the rumor that Good Magic was seriously being considered turned into fact, and the best horse other than the winner in the Kentucky Derby, and the reigning two-year-old champion for that matter, is here to make Justify honest. At his best this colt probably can't beat the heavy favorite, and his connections know it. But he is the second best in this race by a wide margin and could be well positioned to take advantage if things finally become too much for Justify and he shows his first flash of mortality.

Sporting Chance Odds to Win the 2018 Preakness Stakes with Picks and Predictions
by Trevor Whenham - 5/14/2018

Let's pretend that Sporting Chance is well named and that he does indeed have a sporting chance of winning the Preakness. He is a Grade 1 winner with nice breeding and a trainer who has won this race as much as anyone alive. But his last race was putrid, his best races came as a two-year-old and before an injury, and at his best he just doesn't seem to be good enough. We'll look at the colt from a variety of angles, but at the risking of spoiling the read I'll admit that I won't be betting on him.

Diamond King Odds to Win the 2018 Preakness Stakes with Picks and Predictions
by Trevor Whenham - 5/14/2018

The Preakness Stakes this year is all about Justify in the eyes of many, but there are indeed other horses running. One of those horses is new to the Triple Crown trail this year, but he has a trainer who has a perfect record in the Preakness, some solid breeding well suited to this test, four career wins in five finished races, and potentially a serious upgrade in jockeys. So, can Diamond King combine all of that to overcome a serious deficit in the odds and make history by winning the second leg of the Triple Crown and ending the fevered Triple Crown dreams many are having when it comes to Justify?

Quip Odds to Win the 2018 Preakness Stakes with Picks and Predictions
by Trevor Whenham - 5/14/2018

There is the potential for Quip to create some bittersweet feelings in the ownership group. Justify, the Kentucky Derby winner and heavy Preakness favorite, is owned by a group of four partner organizations. Quip, who had the points to make the Derby field but passed on that race while aiming for this one, is owned by three. Two of Quip's owners also own Justify, and the third used to own Justify's racing rights but sold them while retaining his breeding rights. So, in the unlikely event that Quip were to upset Justify, it would probably be the most muted celebration party ever.

Handicapping the 2018 Preakness Stakes Field: Early Look
by Trevor Whenham - 5/9/2018

The Preakness field is almost certainly never as strong as the Derby field - and certainly not as deep. But this year it has gone to an almost ridiculous extreme. We have one super horse, a potential challenger who would be a star many other years but was born at the wrong time, a potentially intriguing new entrant likely not good enough to win, and a bunch of horses just looking to grab a small piece of the $1.5 million purse - because even the minimum payment that comes for finishing fifth is better than you get for winning most races out there.

2017 Preakness Stakes Betting Advice: Handicapping the Pace Scenarios
by Trevor Whenham - 5/17/2017

To effectively handicap any race you need to understand what it is likely to look like. How fast will it be run? Will it favor speed horses or closers? Will your horse be helped or hurt by the race shape? Will any horses have a particular advantage or obstacles that will get in their way of running their best race? In some races the pace scenario is tough to figure out or could look a number of different ways. The Preakness pace scenario, though, is much more straightforward. On paper, at least.

Handicapping the 2017 Preakness Stakes: Jockey Analysis
by Trevor Whenham - 5/17/2017

Those little guys in the saddle will have a big impact on how the Preakness Stakes turns out. It's always the case. This isn't the toughest or craziest race by any means, but there is almost always a strong favorite, and the rest of the Preakness jockeys have to figure out how to maximize their chances while best limiting his potential.

2017 Preakness Stakes Betting and Handicapping: the Trainers
by Trevor Whenham - 5/17/2017

There are nine trainers represented by the 10 runners in the Preakness this year. And it's a wide range - from Hall of Famers and guys who are sure to get there to a guy who has never won a graded stakes race before. What they have in common at this moment is that they all have talented colts in their stable, and they all have them dialed in at the right time of year. Only one will win, and each would become famous - or more famous - with a win here. So, who will it be? And what does each of the Preakness trainers bring to the table?

How to Bet on the Preakness Stakes in 2017: Expert Advice and Handicapping
by Trevor Whenham - 5/16/2017

The Kentucky Derby is a horse race. So is the Preakness Stakes. And they have some of the same horses in them. From a betting perspective, though, that's pretty much where the similarities end. These are two massively different races for bettors, and you need to bet them very differently as a result if you want to have any hope of success.

2017 Preakness Stakes Betting Advice and Handicapping: Live Long Shots
by Trevor Whenham - 5/16/2017

With a strong favorite like Always Dreaming and a strong challenger in Classic Empire, pretty much every other horse in the expected 10-horse field is going to be a long shot to some extent or another. There is a decent chance that all eight horses will go off at 10/1 or higher. You can't bet all eight of them, though - especially because the top two are so tough. Of those eight longer shots, then, there are three that stand out as the most attractive. To be clear, this doesn't necessarily mean they are the most competitive but rather the most attractive at their price. This is all about finding value, not grading these horses. (Futures odds are from Bovada)

Multiplier Odds to Win the 2017 Preakness Stakes with Picks and Predictions
by Trevor Whenham - 5/16/2017

There are broadly three types of horses in the Preakness Stakes this year. There are the horses that ran in the Kentucky Derby, and those five will likely be the five lowest-priced horses in this 10-horse field. Then there are Cloud Computing and Conquest Mo Money, two colts who had the points to run in the Derby but were pointed here instead. And then there are three completely new shooters. Multiplier fits into that group and will likely be the lowest-priced of the group. But is he good enough to be a real contender in the race?