2014 Kentucky Derby: Your HN Cheat Sheet, Part 2

Who should you put your money on this year? Heather Benson breaks down five betting strategies.

If you missed Part 1, check it out here.

From Heather:

The final post positions for this year’s Kentucky Derby were set yesterday, you can get a full run down of got placed good, bad or otherwise here. And now that we know who ended up where, we can take a look at some Horse Nation-exclusive betting strategies for this year’s race.

Betting Strategy #1: Bet the favorite.

He has won all three of his races this year by five lengths or more, he has the “rags to riches” backstory we all love and dang if he ain’t pretty. His fans call themselves “Chromies” and he drew in the post position where 8 Kentucky Derby winners have already won from, post 5. You won’t win much if you do bet him, but there is a pretty good chance you will indeed win.

Are you a “Chromie”? California Chrome will go to the post Saturday as the prohibitive favorite, a honor he has well earned.

 Betting Strategy #2: Bet the gray… or not.

Whenever people are at the track for the first time and ask me what to do, I usually tell them to keep it simple and “bet the gray.” After all, if you had bet the gray in the last 30 or so Kentucky Derbies, you would be money ahead by now thanks to longshots like Giacomo and Gato Del Sol taking the roses. Unfortunately, for the first time in many moons, there isn’t a single gray contender in this year’s Kentucky Derby. And since two of the last three Kentucky Derby winners and three of the last five Triple Crown winners have been chestnuts, perhaps you should revert back to Plan A, above!

The gray Giacomo winning the 2005 Kentucky Derby at odds of 50-1.

Betting Strategy #3: Bet the guys who have won the race the most times.

It is really hard to win the Kentucky Derby, like really hard. Consider that America’s leading trainer for the last several years Todd Pletcher took 24 tries, with the nation’s best and brightest 3-year-olds, before he got his win with Super Saver in 2010. But a blessed few have won the race more than once, so consider adding these guys to your ticket:

Trainer Bob Baffert (three Derby wins) with Chitu (pp 12)

Jockey Gary Stevens (three Derby wins) with Candy Boy (pp 17)

Bob Baffert and Gary Stevens teamed up in 1997 to win the Derby with Silver Charm.

Betting Strategy #4: Bet the guys who are more than due for a win

Some trainers, like Todd Pletcher or Bob Baffert, seem to find a way to enter a horse (or five) in the Kentucky Derby every year, even if they are a no-hoper, and some others only enter a horse when they really, really feel they have a shot.  The Jerkens family, both father Allen and son Jimmy, follow that creed.

Trainer Jimmy Jerkens’ first Kentucky Derby entrant, Wicked Strong, has a real chance of winning the big one.

Jimmy had his best shot at a Kentucky Derby entrant, and a possible win, in 2009 with Quality Road. But foot problems kept him from the starting gate and it has been five years since Jimmy thought he had another one good enough to give the big dance a try. That horse is Wicked Strong and based on his win in the Wood Memorial Stakes a few weeks ago, he seems like a real contender. But to win, he will have to overcome the dreaded 20th post position, a slot from which only one horse has ever won the Derby from before.

Betting Strategy #5: Find a pretty one and throw your money down.

The Kentucky Derby with its 20-horse fields, screaming 160,000+ fans and general insanity is a trial for both man and beast. Anything that can go wrong for a horse often does and even the most even-tempered horses sometimes lose it that first time they set foot on the track in front of crowd that is larger than almost any other sporting event in America. If horses like Mine That Bird and Animal Kingdom have taught us nothing else in recent years, it is that there is no “easy” choice in picking a Kentucky Derby winner.

Mine That Bird winning the 2009 Kentucky Derby at odds of 50-1.

So the bottom line… pick the prettiest, the blingiest, the tallest, the shortest, the one with the prettiest silks and the one with the cutest jockey. It’s a horse race and the main idea is to go with your gut and cheer with all you’ve got when they come down the stretch on Saturday.

The Kentucky Derby is this coming Saturday, May 3 at approximately 6:24 pm EST. It will be shown on TV on local NBC affiliates. A full television schedule can be found here.