Kentucky Derby 2014 Odds: 10 Betting Tips from Handicapping Expert

Michael Dempsey@turfnsportFeatured ColumnistMay 1, 2014

Kentucky Derby 2014 Odds: 10 Betting Tips from Handicapping Expert

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    Matt Slocum/Associated Press

    The Kentucky Derby is the most popular horse race of the year, but it is also one of the toughest nuts to crack. With a 20-horse field (19 currently) of lightly raced three-year-olds that are all trying a distance they have never competed at, it can be one challenging puzzle to solve.

    I have put together some basic betting advice, geared more toward the casual racing fan who may be looking to place a few wagers Saturday. I used these ideas to help me pick Street Sense ($11.80) in 2007, Super Saver ($18.00) in 2010 and Animal Kingdom ($43.80) in 2011.

    Here are 10 betting tips to keep in mind before heading to the betting window (or your computer).

Get Familiar with Betting Options

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    USA TODAY Sports

    This is not your father’s Kentucky Derby. There are so many more betting options today than there were several decades ago, and it is a good idea to become familiar with them.

    The traditional win, place and show are still available, but for horseplayers who want to swing for the fences, there is a wide variety of options. Hitting a trifecta involves correctly selecting the exact order of the top three, and a superfecta involves nailing the top four finishers, which is no easy task with such a large field.

    Want to knock one out of the park? Try hitting the Super High-Five, which involves selecting the top five finishers—a wager that no horseplayer solved last year. A winning ticket would have been worth more than $300,000. has a more detailed explanation of each wager available. Go with your comfort level. If you are more conservative, stick to traditional bets, and if you are looking for a big score, try to knock down a trifecta or superfecta.

Get Rewarded for Your Betting Action

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    Seth Wenig/Associated Press

    To get a wager down on the two most exciting minutes in sports, you do not have to hop on a plane to Louisville. Horseplayers can head out to their local track or off-track betting parlor or just fire up a betting account online. It’s perfectly legal. 

    If you are a new player who is looking to wager online or at the track for the first time, there are plenty of options out there. If you choose to wager online, make sure you are dealing with a secure, reputable racebook.

    No matter how you wager, there are rewards and perks out there. Most online racebooks have generous sign-up bonuses this time of year, and most offer some type of rebates.

    Some will let you lock in betting odds in advance of the race. Check out Odds Shark for a list of the latest Kentucky Derby odds

    Shop around for the best offers, particularly with rebates. Even small bettors can get back a percentage of wagering handle, and that can really help your bottom line.

Do Your Homework; It Can Lead to Profits

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    Charlie Riedel/Associated Press

    There is a wealth of information if you want to do some homework before placing your Derby bets. It certainly beats the old days where the only way you could get past performances and statistics was to wait at the newsstand for the Daily Racing Form to arrive. Often, it didn’t. 

    In the past, if I wanted to watch replays of the Derby prep races, all I had to do was send off $19.95. Two weeks later, I got a CD in the mail.

    Now we can just watch replays online or through the free Equibase app, which has detailed information including replays and results.

    Along with a wealth of Kentucky Derby information here at Bleacher Report, Daily Racing Form, Blood-Horse and Equibase are the go-to sites for horseplayers.

Look for Proven Connections

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    Matthew Stockman/Getty Images

    Sure, many fans had never heard of Chip Woolley before Mine That Bird won the 2009 Kentucky Derby, but one good betting tip is to look for proven connections to be in the winner’s circle on the first Saturday of May. 

    Hall of Fame trainer Bob Baffert has saddled three Derby winners, the last coming in 2002 with War Emblem. Baffert was looking good with second-choice Hoppertunity until the colt was scratched Thursday morning due to an injured foot. The trainer still has long shot Chitu, who won the Sunland Derby in his last outing.

    Last year’s winning trainer was Shug McGaughey, who is a fellow Hall of Famer. Trainer Todd Pletcher is a six-time Eclipse Award winner and a future Hall of Famer, but he has not had much luck in the Derby, going just 1-of-36. He sends out two major players in Danza and Intense Holiday.

    Having a proven jockey can’t hurt. Hall of Fame rider Calvin Borel has won three of the last seven runnings of the Derby and will be aboard Ride On Curlin this year. Fellow Hall of Fame rider (and fellow movie star) Gary Stevens has booted home three Derby winners.

Wager on a Contender with a Foundation

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    Uncredited/Associated Press

    We were going to hear the name Apollo a lot this week if Hoppertunity did not get injured. The Baffert trainee was trying to buck a 100-plus-year trend. Every Derby winner since Apollo in 1882 competed as a juvenile. Hoppertunity did not make his debut until Jan. 4 of this year. 

    While this trend continues on for another year, it is still good to note that Derby winners need a foundation as a two-year-old along with a solid stakes outing as a three-year-old, preferably at 1 1/8 miles.

    Look for contenders that had a sharp race in their final preps, preferably in Grade 1 company, and their best on conventional dirt.

    California Chrome makes the cut. The colt has started 10 times—the most in the Derby field. 

Early Speed Rules in Racing, Except in Derby

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    Doug Pensinger/Getty Images

    If you play the ponies more than just a few days per year, you know that one of the best assets a horse can have is early zip. Speed is very dangerous in racing. 

    However, when it comes to the Kentucky Derby, it is the exact opposite. In fact, no Derby winner has wired the field since War Emblem pulled off the feat in 2002.

    Just 22 horses in the history of the race were able to win by leading at every call. In recent years, we have seen a trend where the early pace has been sharp, which tends to set things up for horses that are coming from off the pace.

    Speed kills in the Derby. This year’s winner is more likely to come from the clouds, but it needs to make its move on the turn and be relatively close when it turns for home.

Look for Historical Trends; They Can Eliminate Pretenders

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    Al Behrman/Associated Press

    With 140 years of history, we have plenty to work with, but with horses racing less, it is better to just go back about 20 years to look for trends that can eliminate a portion of the field from contention.

    • 106 Derby winners were bred in Kentucky.
    • Betting favorites have won just five of the last 25 runnings of the Derby.
    • Since the debut of the starting gate in 1930, post position 17 is the only one among the 20 that has never produced a winner.
    • Only three horses have won the Derby in the last 40 years without a prior graded-stakes victory.
    • Street Sense is the lone Breeders’ Cup Juvenile (G1) winner to win the Derby.

    Many astute handicappers use historical data to assist in picking the Derby winner. Jon White, the morning-line oddsmaker for Santa Anita, came up with a Derby Strikes System.

    The system consists of nine key factors to determine how a Kentucky Derby candidate looks from both a tactical and historical perspective.

Look for Betting Value, Not Chalk

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    Morry Gash/Associated Press

    While much of the hype this week has surrounded California Chrome, keep in mind that a $2 win wager is likely only going to return about $7.00. Going back 25 years, we have seen 20 Derby favorites not get the job done on the first Saturday of May. 

    We have seen some big upsets, including Mine That Bird, who returned $103.20 in 2009, and Giacomo, who paid $102.60 in 2005. Animal Kingdom paid $43.20 in 2011. 

    In all of horse racing, the betting favorite wins just one out of three races. In the Derby, that number is much smaller because the winner not only has to be good but needs to be lucky to make his way through a 20-horse field and hit the wire in front.

    Don’t be afraid of a horse at a price.

Bet Like It’s a Marathon, Not a Sprint

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    Garry Jones/Associated Press

    Yes, the Kentucky Derby is 1 1/4 miles, a distance that these 19 contenders have never run. However, what I am talking about is realizing that Derby Day is a marathon. There are 13 races on the card, with first post at 10:30 a.m. ET. Final post is 7:50 p.m. ET. 

    That is nearly 10 hours of betting action, and that excludes Friday’s Kentucky Oaks card, which features 12 races.

    Don’t throw all your eggs in one basket, or should I say, race. Spread out your bankroll as there will be good betting opportunities throughout the day. And if you fail to come up with the Derby winner, Churchill Downs is nice enough to card two races after.

Have at Least One Mint Julep

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    Jamie Squire/Getty Images

    Handicapping and betting on the Kentucky Derby can be hard work, so you deserve a break. Have at least one mint julep, the official drink of the Kentucky Derby. 

    Just at Churchill Downs, more than 120,000 will be served between Oaks and Derby Day—and probably a million more consumed at Derby parties.

    As a public service, here is The Early Times Mint Julep Recipe, per

    • 2 cups sugar
    • 2 cups water
    • Sprigs of fresh mint
    • Crushed ice
    • Early Times Kentucky Whisky
    • Silver Julep Cups

    Make a simple syrup by boiling sugar and water together for five minutes. Cool and place in a covered container with six or eight sprigs of fresh mint, then refrigerate overnight. Make one julep at a time by filling a julep cup with crushed ice, adding one tablespoon mint syrup and two ounces of Early Times Kentucky Whisky. Stir rapidly with a spoon to frost the outside of the cup. Garnish with a sprig of fresh mint.

    Consuming a few can take the sting out in case you don’t cash a Derby ticket.