You might think that picking a horse to win the Preakness that didn’t run in the Kentucky Derby would make sense. After all, the Derby is a truly brutal test for horses, and the two-week rest following that race is far less than horses are used to now. While there seems to be logic there, history has not proven that to be the case. In the last 29 years of the Preakness, we have seen just three horses that won without having run in the Derby.

It gets even worse when you look closer. Two of those three winners are Bernardini and Rachel Alexandra. Bernardini was an incredibly-talented-though-inexperienced horse who went on to be the star of his class through the summer. Rachel Alexandra was one of the great fillies of the last two decades — at least. Neither horse had entered the Derby, but there is a very solid chance that they would have been able to win that race if they had. They were superstars.

With all due respect to the three new entrants this year, there are no superstars here. I’m not even convinced that there is a minor star among the group of new horses, though you never know what will happen until the race is run.

Departing

This horse is getting by far the most attention of three new contenders to the Triple Crown trail. On fact, there is a decent chance that he could go off as the second betting choice by post time. Of course, Orb will be so heavily favorite that the second choice will have just a small fraction of the support.

The reason for Departing’s support is his win in the Illinois Derby in late April. It was impressive. He bided his time early, made a decisive move, and was clearly best at the wire. While he certainly made a statement with the win, I’m not as convinced as some because he beat absolutely nothing of interest in the race. It was a poor field, so he merely did what he should have by rising above it.

The connections for this horse have a history of upsets in big races. In 2010, trainer Al Stall Jr. gave the all-time great mare Zenyatta her only loss in 20 races when his Blame won the Breeders’ Cup Classic. Last year, jockey Brian Hernandez Jr. won the same race in an upset aboard Fort Larned when Game On Dude was widely expected to win.

There is an interesting background story regarding this horse. He is owned in part by Claiborne Farms, one of the leading stallion operations in the country. One of their biggest clients is the partnership of Stuart Janney III and the Phipps family. That partnership has sent both stallions and mares to Claiborne for years. That partnership also owns heavy-favorite Orb, and that horse is more than likely headed to Claiborne for his stud career. It’s a delicate situation.

Govenor Charlie

First, I have to say that the spelling of this horse’s name is driving me insane this year. Creative spellings are nothing new to racing, but this one is worse than most.

That aside, this is a horse that can’t be entirely overlooked. He is trained by Bob Baffert. Baffert has brought 13 horses to the Preakness over the years and has won the race five times. That’s a darned good winning percentage. One of those wins was with Real Quiet, who not only shares the same ownership as this horse but is also Govenor Charlie’s grandsire.

The horse is very lightly raced, with just three outings under his belt to this point. He has two wins and a second, though. His last win, in the Sunland Derby, was particularly impressive, though it came against weaker competition. He was seriously considered for the Derby as well, though a minor foot injury derailed those plans the week before the race.

He’s very well-bred, and jockey Martin Garcia has won this race before and suits the horse well. The biggest issue, though, is that he is likely to be pressing the pace early on, and that doesn’t appear to be the best place to win this race from this year. He could be a factor, though.

Titletown Five

Trainer D. Wayne Lukas has three horses in the race this year, and this is by far the least impressive. He insists that the horse is training well and is ready for a big showing. I just don’t buy it.

In the Louisiana Derby he was a total non-factor when he finished ninth behind several Derby and Preakness horses. He led briefly early in the race but just couldn’t carry on. He tried again to earn his way into the Derby via the Derby Trial but was an underwhelming fourth. He just doesn’t seem to be nearly good enough to beat the best here.

The only thing even somewhat interesting about this horse is his ownership group, which includes Green Bay Packers legends Paul Hornung and Willie Davis. Unfortunately, they won’t be any help for their horse in this challenge. If Titletown Five makes the board in this one, he’ll do it without my support.

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Read more articles by Trevor Whenham