2023 Kentucky Derby betting overview


Welcome to VSiN’s 2023 Kentucky Derby Betting Guide!


The Derby, which is limited to 3-year-olds, is as much of an American rite of spring as the start of the baseball season and the Masters. This is the 149th Run for the Roses which has traditionally been run on the First Saturday in May, but that hasn’t always been the case. The inaugural Derby was run on May 17, 1875 (the Third Saturday in May), and was mostly run on the second or third Saturday of the month for more than 50 years (with the notable exception of the Fourth Saturday in April on April 29, 1901). It’s been run on the First Saturday in May since May 7, 1932, except for when the 2020 COVID-19 pandemic pushed it back to Sept. 5 (the First Saturday in September).

The Derby is also known as the first jewel in the Triple Crown – which also includes the Preakness Stakes at Pimlico and the Belmont Stakes at Belmont – but that also wasn’t always the case. Daily Racing Form’s Charles Hatton is credited with coining the phrase in the 1930s that led to owners and trainers aiming for those races with their 3-year-olds, but it wasn’t officially recognized until 1950. The previous Triple Crown winners were grandfathered in, even though the series didn’t actually exist when those horses actually accomplished the feat. But in all of our lifetimes, it’s been well-established and a field of 20 will enter the starting gate Saturday to add to the illustrious history.

As a marquee sporting event, the Derby is often the only horse race that most people pay attention to during the year. While this Betting Guide is certainly for our regular horse-playing subscribers at VSiN, it’s also meant as a primer to help the casual fans catch up on this year’s Derby field and offer advice on how to bet the race as well as Friday’s Kentucky Oaks for 3-year-old fillies, and the undercards on each day.

It’s probably obvious, but the top contenders for the Derby are generally the winners of the major prep races that have been run this spring. #15 Forte is the 3-1 morning-line favorite off his win in the Florida Derby at Gulfstream Park on April 1. (He also won the Fountain of Youth at that same track on March 4.) #5 Tapit Trice is the second choice at 5-1 after winning the Blue Grass Stakes at Keeneland on April 8 (and the Tampa Bay Derby on March 11). The third choice is #14 Angel of Empire at 8-1 off of his win in the Arkansas Derby on April 1 while co-fourth choice #10 Practical Move is 10-1 after winning the Santa Anita Derby on April 8.

If you’re most concerned about making a profit on the race, the winner is most likely coming from that group. The last four Derbys have been won by horses paying double-digits, but the 2010s had several winners with single-digit payouts under $10: eventual Triple Crown winners American Pharoah in 2015 ($7.80 on a $2 Win bet at odds of 5-2) and Justify in 2018 (also $7.80), as well as California Chrome in 2014 ($7) and Nyquist in 2016 ($6.60).

However, the thing that makes betting the Derby so great is that it’s just as likely that we get a long-shot winner. These are young horses (think of them as teenage boys) that are still developing. The winner could be a colt with a lot of racing experience, or it could be one that’s peaking at the right time come Derby Day. The best 3-year-old doesn’t always win the Derby; it’s often just the one that’s best on the First Saturday in May.

Remember, these colts are running the 1 1/4-mile distance for the first time. They’re contending with the biggest crowd they’ve ever heard, and then trying not to get taken out in the cavalry charge to the first turn, having to overcome the traffic in a 20-horse field. A lot can go wrong even if you’ve bet on the “best horse.”

Just last year, #21 Rich Strike shocked just about everyone by winning at 80-1. He wasn’t even in the official field until another colt withdrew from the race before the Friday scratch deadline, and he had to break from the far outside post. But he’s far from the only bomb that’s exploded the Churchill Downs tote board as Country House won in 2019 (65-1), I’ll Have Another in 2012 (15-1), Animal Kingdom in 2011 (21-1), Mine That Bird in 2009 (50-1) and Giacamo in 2005 (50-1).

If you’re looking for a longer price, you have the vast majority of the field to choose from. #3 Two Phil’s won one of the lesser prep races, the Jeff Ruby Steaks, on an all-weather track at Turfway Park, but he appears to be the “wise guy” horse at 12-1. #9 Skinner was on the outside of the 20-horse field looking in like Rich Strike, but an early scratch put him into the main part of the field and is the relatively low price of 20-1. #11 Disarm snuck into the field in the very last prep race – the Lexington Stakes at Keeneland just 3 weeks ago on April 15 – by earning enough qualifying points with a third-place finish. The longest long shots of all are at 50-1 with #7 Reincarnate, #13 Sun Thunder, #16 Raise Cain, #20 Continuar and the also-eligible #23 King Russell. While many will scoff and say those odds are too short, we’ve already shown that plenty of similarly ignored long shots have won the Derby. It stands to reason that at least one will significantly outrun his odds and be in contention down the stretch. The problem is figuring out which long shot.

And because of the wide-open nature of the race and the huge field, the exotics can pay huge. If you’re able to connect the dots, the Exacta (pick the first two finishers) usually pays in the $100s – led by a $3,009.60 Exacta in 2019 with 30-1 Country House, who actually ran second but was declared the winner after 9-2 Maximum Security was disqualified, topping 14-1 Code of Honor. Tacticus finished third at 5-1, but the Trifecta (pic the top three finishers) still paid $11,475.30. The Trifecta usually pays in the $1,000s (except in years when the chalk wins like with American Pharoah and Justify).

The Superfecta (pick the top four finishers) is even harder, but it can be life-changing money as the 2005 Giacomo super paid a record $864,253.50 with the 2009 Mine That Bird super paying $557,006.49 and the 2010 Super Saver super returning $101,284.60.

So, while you’re going through the profiles of this Saturday’s contenders (note we’ve included the also-eligibles from #21 to #23 just in case one draws in like Rich Strike last year) and the picks of VSiN’s hosts and handicappers to help mesh with your own handicapping, we hope we help you find the winner. But also – to borrow from baseball and the Masters – take this opportunity to swing for the fences and create your own Cinderella story.

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