Wagering on Triple Crown the Holy Grail for Horseplayers

There is literally horse racing betting 364 days a year, but for three Saturdays each spring horseplayers gather for what is considered the Holy Grail of horse betting — the three jewels of the Triple Crown.

It starts on the first Saturday of May with the Kentucky Derby, best known as the two most exciting minutes in all of sports. Two weeks later it is on to Baltimore for the Preakness Stakes, and three weeks later all eyes are on the Big Apple for the Belmont Stakes.

With tens of millions wagered on each event, it is a great time for horseplayers to jump into the multitude of betting pools, an almost endless list of ways to pad the bankroll.

The Kentucky Derby is a unique handicapping puzzle, as it is the only race in the U.S. where there are 20 runners. Add in the fact they are lightly raced three-year-olds going 1 ¼ miles for the first time in their careers, and coming up with the winner is a challenge.

We have seen the betting favorite win three years in a row, but over the past three decades the average winner has returned nearly $27 for a $2 win wager.

Before these last three years, 12 of the last 13 winners of the Run for the Roses paid at least $10.20 and we have seen two 50-1 longshots score, Giacomo paying $102.60 in 2006 and Mine That Bird returning his few backers $103.20 in 2009.

The $2 exacta with Giacomo and Closing Argument (70-1) returned a record $9,815 while Mine That Bird and Pioneerof the Nile (6-1) combined to pay $2,075.

The Preakness Stakes tends to favor logical horses with the average payoff over the last three decades just $10.50.

However, we have seen some big upsets recently, including Oxbow ($32.80) in 2013 and Shackleford ($27.20) in 2011.

One of the biggest recent exacta payoffs involved War Emblem, who was sent off at 5-2 and who added the Preakness to his Derby win. Longshot Magic Weisner, a local horse, rallied for the runner-up spot and they combined for a $327 exacta.

The Belmont Stakes has produced plenty of upsets in recent years, and over the last three decades the average winning payoff is $26. Creator added to those numbers with his upset in 2016, returning $34.80.

We have seen some monster payoffs in the third jewel of the Triple Crown including Sarava ($142.50) in 2001, Birdstone ($74.00) in 2004, Da’Tara ($79.00) in 2008 and Ruler On Ice ($51.50) in 2011.

The exacta with Sarava and Medaglia d’Oro (16-1) tops the scales, the $2 ticket coming back at a hefty $2,454.

The shortest priced winning favorite we have seen in the past three decades was American Pharoah, who completed his Triple Crown by returning just $3.50 to win in 2015.

Michael Dempsey provides his handicapping analysis daily at turfnsport.com.