Q&A With Barstool Sports Founder, Racehorse Owner David Portnoy

August 10th, 2015

David Portnoy pictured with one of the racehorses he co-owns, Smokeshow City. (Photo courtesy of David Portnoy)

David Portnoy is the founder of Barstool Sports and a current Thoroughbred racehorse owner. One of his horses, Smokeshow City (pictured), has a win and a second in six career starts and is currently stabled at Del Mar in Southern California. Jose Contreras chatted with him to learn more about his love of horse racing and gambling.

How and when were you introduced to Thoroughbred racing?

My dad took me to Rockingham Park in New Hampshire as a kid. We used to go every year. Probably 10 years old or so.

How many horses do you own?

I own parts of six horses.

What led you to become an owner?

I always thought it would be fun. I’d rather lose my money owning horses than betting horses. So a couple buddies and I got together and bought the first one together. Now I’m hooked.

You attended the 2013 Breeders' Cup at Santa Anita with Wes Welker. Who's a better handicapper, you Wes?

Wes is a strange handicapper. He places 8,000 bets and spends five hours at the window. I feel like he’s one of those guys who always cashes a couple tickets every race but got murdered. But he’s still better than me, just ‘cause I stink.

When you first launched Barstool Sports (newspaper) you had a focus on gambling. Have you always been a gambling man?

Always. First website I launched in college was www.thegamblingman.com.

I'm more of a Win, Daily Doubles, and Pick 4 bettor. What do you like to bet?

I’m almost always a win guy.

Do you think there is something holding back horse racing from going back to full mainstream coverage and the popularity levels like it once was?

It certainly doesn’t help that anytime a horse becomes famous (American Pharoah) they retire quickly. It’s hard to keep national interest if your best athletes have two-year careers.

After experiencing your first Kentucky Derby this year, would you rather go to the Derby or Breeders’ Cup every year?

Breeders’ Cup a million out of a million times. I enjoyed the Derby. I had to do it, but it was a scene. Breeders’ Cup is more for horse people. Derby is just a huge party where horses happen to be there.

This was your first Derby and now we have the first Triple Crown winner in over 37 years. Do you think anyone can beat American Pharoah this year?

I’d be interested to see what a healthy Texas Red can do.

TEXAS RED

Photo by Eclipse Sportswire

Are you going to this year's Breeders’ Cup? If yes, have you ever been to Keeneland?

I am going this year. I can’t wait. I’ve never been to Keeneland which is why I’m so excited.

Do you have horse betting superstitions? Like betting on grays or always watching races from the same spot or things like that?

Big time. I love betting grays, and Nos. 6, 10 and 11. If I can’t decide on a horse those will be deciding factors.

If you were to form a partnership to own horses which three sports athletes/celebrities would you invite to the group and why?

Hmm, tough one. Wes would be in there since I know he loves horses. Probably Tom Brady since he goes to the Derby and I could just stare at him and Bill Belichick. Guy just wins.

What has been your largest winning bet on horses?

Probably about $10,000 on Roman Approval which is a horse I have a stake in. Great horse.

Your favorite racetrack?

Saratoga hands down. Nothing is even close in my mind.

What racetracks would you like to visit?

Keeneland and I’d love to check out Royal Ascot.

Your favorite Thoroughbred racing event?

Can I say the entire month of August at Saratoga? If not it’s the Breeders’ Cup.

Other sports/teams you follow?

All Boston teams. For college I’m a Michigan man.

Favorite all-time Thoroughbred?

Holy Bull

What is your personal best moment in the sport of Thoroughbred racing?

It’s an obscure one, but I remember going to Saratoga with my dad as a kid. We did a Tri Key with Dehere on top of the entire field. It was very expensive bet for the Portnoys at the time. Dehere was boxed in with nowhere to go and took a right hand turn and won from the clouds. Still one of the best moves I’ve ever had.

I also remember my dad winning the 1989 Derby with Sunday Silence and he cashed his ticket and put all the money in a draw and my sister and I got to pick out a bill. I got a 20 which was huge cash for a 12 year old.

Best racetrack food can be found at:

Saratoga. Duh.

Your favorite jockey:

Riding now would be Irad Ortiz Jr. Huge Gary Stevens fan as well.

IRAD ORTIZ JR.