2019 Preakness Stakes Long Shots: Advice and Expert Betting Tips for Value

It says here that the purpose of this article is to pick out some Preakness live long shots. And that is just what we are going to do. But before I get to that, I have to be honest - I am not at all convinced that a long shot is going to win this race. It feels very top heavy as it has set up. So, these long shots are probably more about filling out the exotics than coming out on top - at least in my eyes. There is a pretty good reason for that. For the most part, the winner of this race comes for the Derby. The reasoning is pretty simple - if a horse is good enough to win this race, he was probably good enough to make the Derby field, and it is extremely rare for a horse not to run in the Derby if he is capable of getting in. So, the best horses typically come from the Derby. And even though we don't have the Derby winner this year - either of them - we still have clearly the two best horses in this race from that field. They are going to be very tough to beat.
There have been just three horses since 2000 that have won the Preakness without having run in the Derby. The first was Bernardini in 2006. He skipped the Derby but was still a supremely talented horse who stood out in the race and has gone on to be a very good sire. He is miles better than any new runner here. Rachel Alexandra was also a new runner in 2009, but she had run in the Kentucky Oaks the day before the Derby, which is the next best thing. She was as close as you can get to being a Derby horse without being one. And the third was Cloud Computing, who actually earned enough points to make the 2017 Derby, but his connections passed because he was a young horse. He ran into a pretty underwhelming Derby winner in Always Dreaming and came out on top. So, the winners from outside the Derby are the clear exception, and they are typically some kind of special.
With that said, here are the three long shots - which I defined as at higher than 10/1 on the morning line - that stand out above the rest. I don't want to dwell on the past, but when we did this same exercise for the Kentucky Derby the first horse listed was Country House, and that paid out nicely.
Bourbon War (12/1): The breeding of this horse stands out. He has the impressive stamina that come from being a son of Tapit - the sire of three Belmont winners - combined with speed that comes from having Breeders' Cup Mile winner Artie Schiller as his damsire. His last race was way back on March 30 in the Florida Derby. He finished fourth, but the result was better than it appears. That was the race in which Maximum Security was allowed to run on the lead over incredibly slow fractions, and it messed the whole race up. This colt did the best he could in the circumstances. The Fountain of Youth, in which he was second, was also a weird race, with the early pace being crazy fast, which caused the leaders to blow up in a big way. So, the pace has driven too much of his stakes career - those were his only two stakes races. We haven't seen his full talent yet, and with a more legitimate pace - which seems likely here - he could finally show what he can do. I'd like him more if he wasn't coming off such a layoff, but he's a factor here.
Warrior's Charge (12/1): There is a lot not to like here - he has won only twice, with a win in a maiden race and another in an allowance race last time out. He's making his stakes debut here and running away from Oaklawn Park for the first time since his debut at Churchill last fall. It's not ideal, to say the least. And he's one of two speed horses, along with Alwaysmining, so he could have to do too much too soon. So, normally, I'd rule him out. But two things make me think. First, Javier Castellano is on board for the first time. That's a serious rider for a horse in this spot. And second, and more significantly, the horse was not Triple Crown nominated, so the owners had to pay $150,000 to supplement him to this race. That seems insane based on what the horse has done, but people who have seen the horse much more than any of us thought it was worth a risk, so we have to pay at least a little attention.
Win Win Win (15/1): His Kentucky Derby was a bit of a mess. He didn't fire, didn't look comfortable on the sloppy surface, and finished 10th without menacing in any way at all. It was pretty ugly - or at least totally underwhelming. But his breeding is excellent - his damsire and grandsire both won both the Derby and the Preakness. And all three of his prep races this year were pretty solid. If he runs back to his best, he can get a piece of the action here. This price seems too high.
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Read more articles by Trevor Whenham
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