Betting the Exotics in the Triple Crown: The Player’s Guide to Wagering and Winning on America’s Biggest Race Days

The year was 1993 and I had the pleasure of watching the 119th running of the Kentucky Derby from my parent’s living room at the Jersey shore. It wasn’t exactly the prestigious scenery and vibrant atmosphere of historic Churchill Downs, but it was the next best thing at the time for a single guy in his early 20s. When Jerry Bailey guided Rokeby Stables Sea Hero to a flawless ground-saving trip to the winner’s circle, I’m not sure who was more excited or startled that day. It could have been my father who was bellowing in delight after 11 Miller Lights and a $400 win bet, or our ex-racing Florida Greyhound Turbo who scurried to safe hiding in an empty bedroom when the chants of “Come on Jerry!” “Get Through Jerry!” echoed through the living room during the stretch run. Sea Hero returned a healthy price that afternoon of $27.80 to win, $12.80 place and $8.00 to show. It was enough to make any fan holding a winning ticket happy, and all was well that spring afternoon at the shore.


Triple Crown Trivia: Celebrating the Sport of Kings

As we embark on a monumental Triple Crown trail kicked off by the 150th Kentucky Derby, we are excited to celebrate the season with some facts and fun stuff to share with your horseracing friends.

150th Kentucky Derby – Saturday, May 4, 2024

Churchill Downs Racetrack – Louisville, Kentucky

The Kentucky Derby is held annually on the first Saturday in May at Churchill Downs Racetrack in Louisville, Kentucky. Celebrating its 150th running in 2024, the traditions run deep and the winner will have a shot and being crowned a Triple Crown champion by winning the following two jewels of the trail with the Preakness and Belmont.


  • 2024 Purse: $5 million
  • Race Length: 1 ¼ miles
  • First Winner: Aristides (1875) – 2:37.75
  • 2023 Winner: Mage – 2:01.57 – 15-1 odds
    Trainer: Gustavo Delgado – Jockey: Javier Castellano
    Win: $32.42 – Place: $14.58 – Show: $9.08
    $2 Exacta: $330.44 – $0.50 Trifecta: $491.18 – $1 Superfecta: $15,643.65
  • Fastest Winner: Secretariat (1973) – 1:59.4 – 3-2 odds
    Win: $5 Place: $3.20 Show: $3
  • Winningest Trainers: Ben Jones and Bob Baffert with 6 each. Jones won in 1938, 1941, 1944, 1948, 1949 and 1952 and Baffert won in 1997, 1998, 2002, 2015, 2018 and 2020.
  • Winningest Jockeys: Eddie Arcaro and Bill Hartack with 5 each. Arcaro won in 1938, 1941, 1945 and 1952 and Hartack won in 1957, 1960, 1962, 1964 and 1969.
  • Who’s the Favorite? Forty winners have won as the favorite in the race.
  • Tasty Tradition: The traditional drink is the Mint Julep, consisting of Kentucky Bourbon, simple syrup, fresh mint and crushed ice. Over 120,000 of the delicious cocktails are sold each year.
  • Trophy Trivia: The trophy weighs 3.5 pounds and is custom made each year for the champion. The owner receives a gold trophy while the trainer, jockey and breeder win a silver half size replica of the main gold trophy.The first documented trophy for the Kentucky Derby was in 1925 for the 50th “Golden Anniversary” of the Derby. Churchill Downs president at the time, Matt Winn, commissioned artist George L. Graff to design the trophy.The 18-karat gold horseshoe on the trophy was pointed downward until Derby 125, when the change was made to turn the horseshoe so the ends pointed up. Superstition says the luck will run out of the horseshoe if it’s pointed down.

    The completed trophy takes approximately 2,000 hours of labor to make, and 29 parts are combined into 19 components to make the trophy.

  • Wearing the Roses: A tradition dating back to 1896, the winning horse receives a garland of red roses that is draped over the saddle and prominently displayed for all to see. The garland consists of more than 400 roses, is two and a half yards long and weighs about forty pounds. Historically, the roses were grown in Louisville, Kentucky by the Dreisbach family wholesale florist. The roses are now imported from warmer climates and assembled at a local Kroger grocery store location for fans to see.


  • Sing the Song: A longtime tradition at the Kentucky Derby is when the entire crowd pauses and sings “My Old Kentucky Home” as the horses prance onto the track for the running of the race. The University of Louisville Marching Band leads the sing-along with the full musical rendition.


149th Preakness Stakes – Saturday, May 18, 2024

Pimlico Race Course – Baltimore, Maryland

Held annually two weeks after the Derby, the Preakness Stakes is the middle jewel in horse racing’s Triple Crown. Run at Pimlico Race Course in Baltimore, Maryland, it challenges 3-year-old thoroughbreds over a slightly shorter distance of 1 3/16 miles. Nicknamed “The Second Saturday in May,” it features similar traditions like elaborate hats, festive crowds and tasty cocktails.


  • 2024 Purse: $2 million
  • Race Length: 1 3/16 miles
  • First Winner: Survivor (1873)
  • 2023 Winner: National Treasure – 1:55.12 – 4-1 odds
    Trainer: Bob Baffert – Jockey: John Velazquez
    Win: $7.80 Place: $4.00 Show: $2.60
    $2 Exacta: $31.80 – $0.50 Trifecta: $12.10 – $1 Superfecta: $72.40


  • Fastest Winner: Secretariat (1973) – 1:53.00 – 1-1 odds
    Win: $2.60 – Place: $2.20 – Show: $2.20
  • Winningest Trainer: Bob Baffert with eight wins in 1997, 1998, 2001, 2002, 2010, 2015, 2018 and 2023.
  • Winningest Jockey: Eddie Arcaro with six wins in 1941, 1948, 1950, 1951, 1955 and 1957.
  • What’s with the weathervane? Completely unique to the Preakness is the famed historic weathervane, a tradition since the Preakness’s return to Baltimore in 1909. The weathervane originally sat atop of the member’s clubhouse and when it was destroyed by fire in 1966, a replica of the building’s cupola was built to stand in the winner’s circle in the infield. According to the official Preakness site, “as soon as the Preakness winner has been declared, a painter climbs a ladder to the top and applies the colors of the victorious owner’s silks on the jockey and horse which are part of the weather vane.”
  • Trophy Trivia: The Preakness trophy, the Woodlawn Vase, is considered the most valuable trophy in sports. It was crafted in silver by Tiffany & Co. and had an estimated value of more than $4 million in replacement value. The vase is named the Woodlawn Vase because during the Civil War it was buried at Woodlawn Farm in Kentucky so as not to be discovered and melted into shot for Confederate Army soldiers.
  • Running the Distance: The Preakness has been run at seven different distances: ?1 ½ miles: 1873–1888, 1890; ?1 ¼ miles: 1889; ?1 1/16 miles: 1894–1900, 1908; 1 mile and 70 yards: 1901–1907; 1 mile: 1909, 1910; ?1 1/8 miles: 1911–1924; ?1 3?16 miles: 1925-present
  • Black Eyed Susan Celebration: The winning horse at the Preakness is draped with a colorful blanket made of thousands of yellow daisies, with black centers painted on to resemble Black-Eyed Susan flowers (Maryland’s state flower) that do not bloom until June in Maryland. It takes four people eight hours to create the blanket. This tradition began in 1940.To honor the tradition, the Black-Eyed Susan Cocktail was created and made with 1 ounce of Kentucky bourbon, 1 ounce of vodka, 1 ounce of peach schnapps, 2 ounces of orange juice, 2 ounces of sour mix and an orange slice and cherry for garnish.


Belmont Stakes – Saturday, June 8, 2024

Belmont Park – Elmont, New York

The Belmont Stakes, the final leg of the Triple Crown, is the toughest test along the Triple Crown trail with a distance of one and a half miles at Belmont Park in New York. Held five weeks after the Derby, it’s the race where champions are truly forged. Only 3-year-olds can compete, and the winner is famously adorned with a blanket of red carnations, New York’s state flower. If the winning horse has also won the Kentucky Derby and the Preakness Stakes, they will earn the coveted Triple Crown Champion status and a $5 million bonus.


  • 2024 Purse: $2 million
  • Race Length: 1 ½ miles
  • First Winner: Ruthless (1867)
  • 2023 Winner: Arcangelo – 2:29.23 – 7-1 odds
    Trainer: Javier Castellano – Jockey: Jena Antonucci
    Win: $17.80 Place: $7.20 Show: $4.90
    $2 Exacta: $68 – $0.50 Trifecta: $66.62 – $1 Superfecta: $133.24


  • Fastest Winner: Secretariat 2:24.00 (1973)
    Win: $2.60 – Place: $2.20
  • Winningest Trainer: James Rowe with eight wins in 1883, 1884, 1901, 1904, 1907, 1908, 1910 and 1913.
  • Winningest Jockey: Eddie Arcaro with six wins in 1941, 1942, 1945, 1948, 1952 and 1955.


  • Trophy Trivia: The Belmont Stakes trophy is a Tiffany-made silver bowl that is 18 inches high, 15 inches across and 14 inches at the base. A silver figure of Fenian, the winner of the third running of the Belmont Stakes in 1869, sits on the top of the bowl. The bowl is supported by three horses representing the three foundation thoroughbreds — Eclipse, Herod and Matchem. The trophy was originally presented by the Belmont family as a perpetual award for the Belmont Stakes in 1926. The winning owner is given the option of keeping the trophy for the year their horse reigns as Belmont champion. The owner of the winner of the Belmont Stakes also receives, permanently, a large silver tray with the names of the previous Belmont winners engraved on it. There are also trays for the winning trainer, jockey and exercise rider as well as mementos for the groom.
  • Trying for the Triple Crown: There have been 29 horses enter the Belmont Stakes with a chance to win the Triple Crown. Only 13 have come away with horse racing’s biggest prize. American Pharoah became the first to do so in 2015 since Affirmed way back in 1978.


  • White Carnation: The white carnation is the traditional flower of the Belmont Stakes and a blanket of flower is worn by the Belmont Stakes winner. It takes 10 man hours to put together and consists of approximately 700 carnations that are glued onto a green velveteen spread. The flowers are shipped in from either California or Bogota, Colombia.


  • Big Sandy: Belmont Park is the largest dirt track in North America at one and a half miles long, making the Belmont Stakes the most grueling of the three Triple Crown races. In addition, it is known as one of the most challenging tracks out there because of the sandy terrain, which makes it harder to navigate through earning the nickname ‘Big Sandy’.


From Foal to the Winner’s Circle: The Journey of a Kentucky Derby Champion

It’s the race that every “horse person” perpetually dreams of winning. In fact, if you combined the available spoils from every other prestigious route that is run throughout the calendar year, the pooled glory would still pale in comparison to that eternal title that is bestowed on the “First Saturday in May”. Alas, the odds against a thoroughbred cantering into that exclusive infield Winner’s Enclosure at Churchill Downs that is reserved specifically for the Kentucky Derby Champion are much more astronomical than you might think.

It follows then that we now tag along on the journey an equine takes from conception, to being royally draped with a blanket of rich red roses.


Slot Floor Sensations: Our Top Picks

When it comes to creating a perfect environment to entertain adults with a variety of wants and desires, casino resorts seem to have it figured out. From fantastic dining to the lavish luxuries like spas and cabanas, casinos offer their guests the best of the best to insure they are satisfied and keep coming back.

We caught up with some of our preferred properties to find out about their casino floors, the variety of games they have and why their guests like to play there.


Craps Strategy: Betting Trends is a Bad Trend

Craps is a table game with multiple bets, most of them awful, some are horrendous, and others are okay. Most players like to make Pass Line bets, which come out to a loss of $1.41 per $100 wagered. That means the house has a 1.41 percent edge on this bet – not bad at all.


Many players also like to place numbers (which means go right up on the numbers) and the house edges for this kind of bet go from decent (1.52 percent on placing of the 6 and 8); to terrible (4 percent on the 5 and 9) to suicidal (6.67 percent on the 4 and 10).


Many players also love to make what my mentor the late Captain of Craps called Crazy Crapper bets (see my book Casino Craps: Shoot to Win!). These are bets that come in with extremely high house edges ranging from single roll bets such as the Field (5.55 percent) to the Yo and 3 (11.11 percent) to the Big Red, also called Any Seven (16.67 percent) to multi-roll bets such as the Hard 4 and 10 (11.11 percent) and the Hard 6 and 8 (9.09 percent). These are just some of the many Crazy Crapper bets that lurk to undo the unwary, unwise and unaware craps player and as the Captain said, “You have to be crazy to make these bets.”


2023 Breeders’ Cup Preview: Our Top Picks

In the world of thoroughbred horse racing, the Triple Crown Series (and its protracted string of “qualifying races”) takes center stage from late February to early June.  However, when the scorching heat finally gives way to Autumn’s wintery preamble, every horse player worth their salt starts to pine over an impending occasion known as the Breeders’ Cup World Thoroughbred Championships.  Scheduled to unfold on November 3rd & 4th at Santa Anita Park in Arcadia, CA, this year’s 14 race Breeders’ Cup card will ultimately confer a whopping $31 million dollars in combined purse money!


Thus far, 2023 has been a “mixed bag” whereas a different three-year old horse prevailed in each of the Triple Crown Series’ three historic races (i.e., the Kentucky Derby, Preakness Stakes and Belmont Stakes).  Another key dynamic currently playing out is the fact that unlike last year (when Flightline was far and away the best older dirt horse in the country), there is currently no “senior statesman” that overwhelms with regards to the Breeders’ Cup’s “Classic Division”.  Moreover, since the Breeders’ Cup offers other divisions which are restricted to: juvenile equines, fillies and mares, sprinters, and turf specialists, we need to evaluate several horses who could help us accrue some extra holiday spending money come November 3rd & 4th.

Mage wins the 2023 Kentucky Derby. (Photo courtesy of Churchill Downs Inc.)

Mage – Even though Mage entered the Kentucky Derby off an impressive 2nd place finish to Forte (2022 Two-Year-Old Horse of the Year) in the Florida Derby, he still garnered little respect at the betting windows.  As a result of rewarding his faithful followers with a $32.40 win mutual (payout based on a $2 wager), this medium sized son of 2019 Kentucky Derby runner-up Good Magic is consequently on a collision course with the Breeders’ Cup Classic.  (Essentially the Breeders’ Cup’s “Main Event”, the $6 million dollar Breeders’ Cup Classic is a 1 ¼ mile contest open to three-year-olds and up.)  Although traditional handicapping logic says to lean towards older horses in the Breeders’ Cup Classic, Mage could be a factor if he gets the same solid pace up front that helped him close like a freight train in the Kentucky Derby.  Top Three Finish Possible.     


National Treasure – This three-year-old Bob Baffert trainee finally lived up to his hype when he went wire-to-wire in the 148th edition of the Preakness Stakes earlier this year.  Despite the presence of Mage, this was nevertheless, one of the weaker Preakness fields I’ve seen in my three decades of covering thoroughbred horse racing.  A runner who did manage to secure 3rd in the 2022 1 1/16th mile Breeders’ Cup Juvenile, National Treasure seems more like an “underneath” type whether he contests the Breeders’ Cup Classic or Breeders’ Cup Dirt Mile.  Use in Trifectas and Superfectas.

Arcangelo won the Belmont and the Travers Stakes. (Photo courtesy of Chelsea Durand/NYRA)

Arcangelo – By virtue of winning the 2023 Belmont Stakes with Arcangelo, Jena M. Antonucci became the first female conditioner to conquer any leg of the Triple Crown Series.  Sired by renowned 2023 Hall of Fame inductee Arrogate, the lightly campaigned Arcangelo has flashed the same sort of brilliance that his father displayed ahead of winning the 2016 Breeders’ Cup Classic as a three-year-old.  One who relishes longer distances, Arcangelo therefore logically figures to be in the mix as they turn for home in the Breeders’ Cup Classic.  Win Contender.


Forte – In the cruelest twist of fate imaginable for charismatic owner Mike Repole, this “Morning Line Favorite” for the 2023 Kentucky Derby was scratched 24 hours before post-time because of a hoof bruise.  Upon his return, Forte ran a respectable 2nd in the Belmont Stakes behind Arcangelo however much like he did in the Florida Derby, this son of Violence seemed to “run in spots” throughout the Triple Crown’s third jewel.  In that he hasn’t progressed speed figure wise since his two-year-old season and will likely be over bet, I will hence leave Forte off my Breeders’ Cup tickets.  A “hayburner”.


Two Phil’s – Since he punched his ticket for the Kentucky Derby by virtue of a dominating score in the 1 1/8 mile G3 Jeff Ruby Stakes at Turfway Park, Two Phil’s was accordingly labeled a “synthetic specialist” by many prominent handicappers.  Alas, a subsequent 2nd place finish in the “Run for the Roses” all but debunked the aforesaid theory.  A next out winner of the Ohio Derby over the highly regarded Bishops Bay, Two Phil’s is exhibiting the kind of ascending trajectory that should concern his competition. Top Contender.


Cody’s Wish – Godolphin Stable initiated a feel-good story for the ages when they named one of their prized purchases after Cody Dorman (a young man who is bravely battling a rare genetic disorder called Wolf-Hirschhorn Syndrome).  Your 2022 Breeders’ Cup Dirt Mile Champion, Cody’s Wish (as of this writing) is riding a six-race winning streak and will be extremely tough to run down in the shadow of the San Gabriel Mountains. Top Selection – Breeders’ Cup Dirt Mile.


Pretty Mischievous – In the aftermath of upsetting this year’s Kentucky Oaks field at odds of 10-1, this gifted three-year-old filly gutted out an impressive victory in Belmont Park’s prestigious G1 Acorn Stakes.  One who will logically take money in the 1 1/8 mile Breeders’ Cup Distaff, Pretty Mischievous will nevertheless have to contend with a fairly solid “older female” contingent that includes: Clairiere, Nest and Secret Oath. Contender in wide open affair.  


Elite Power – A surprise 5-1 winner of the 6-furlong (¾ mile) 2022 Breeders’ Cup Sprint, Elite Power is thus far undefeated in 2023.  Looking to become just the third back-to-back winner (Midnight Lute, Roy H) of perhaps the Breeders’ Cup’s trickiest race, this speedy son of Curlin (2007 & 2008 Horse of the Year) will have to fend off the ever improving Straight No Chaser and several other staunch sprinters. Repeat in realm of possibility.


Modern Games – Managed by legendary Godolphin conditioner Charles Appleby (12 Breeders’ Cup wins), Modern Games scored as the 6/5 favorite over Keenland Racetrack’s firm turf course in last year’s Breeders’ Cup Mile.  Guaranteed to be targeted by some top European invaders, Modern Games will similarly have to fend off the likes of: Up to the Mark, Exaulted and Chez Pierre. The one to beat.


In Italian – If there is any horse with an axe to grind in this year’s Breeders’ Cup, it is In Italian.  A game runner up to Tuesday in the 2022 Breeders’ Cup Filly and Mare Turf, this chestnut mare has the marked advantage of retaining 16-time winning Breeders’ Cup conditioner Chad Brown. Gets her revenge.


Given the full and highly competitive fields that materialize every year, the Breeders’ Cup World Thoroughbred Championships absolutely own the potential to confer a “life changing score”.  Having followed this event every year since 1997, I would advise a handicapper to split their bankroll (say $200) between their two or three of their favorite “Win” bets and a fair share of exotic wagers (trifectas and superfectas).  After all, with the rate of inflation these days, losing two bills really isn’t a big deal.  Then again, hit the right $2 superfecta, and you’ll be taking an early retirement somewhere along the coast of Monaco!


By Eric Floyd