Tom Pedulla is interviewing prominent owners, trainers and jockeys for America’s Best Racing as they travel the Road to the $3 million Kentucky Derby presented by Woodford Reserve. The Derby has been rescheduled for Saturday, Sept. 5, due to the COVID-19 pandemic.

Peter Callahan, 78, owner of Swiss Skydiver, is featured this week. The chestnut daughter of Daredevil attempts to make history today at Keeneland Race Course as she aims to become the first filly to win the $600,000 Toyota Blue Grass Stakes since the race was established in 1937.

Swiss Skydiver, a $35,000 find for trainer Ken McPeek at the 2018 Keeneland September yearling sale, is set to become only the second filly to test males in the 1 1/8-mile Blue Grass. Harriet Sue ran fifth in 1944, a year in which Keeneland’s Spring meet was held at Churchill Downs.

Swiss Skydiver is set to break from post-position 7 in a field of 13 with Mike Smith aboard. She will carry 118 pounds, five fewer than her male counterparts. Post time is set for 5:30 p.m. ET.

The Blue Grass, which is being sponsored by Toyota for the 25th year, will award Kentucky Derby qualifying points to the top four finishers on a 100-40-20-10 basis.

PEDULLA: When did you enter the racing industry as an owner?

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CALLAHAN: It was in the mid-80’s. I was always interested in horses. I come from Astoria (N.Y.) and it was not uncommon for guys to put some money together and bet some horses at Aqueduct or Belmont.

PEDULLA: And it progressed from there?

CALLAHAN: I did get the bug. I got bit by something not quite as strong as the coronavirus, but it was a strong bug because I’ve been in the business one way or another ever since, mostly breeding and selling for the last 15 years and to some extent racing with not much success. I’ve had a few good horses over the 30 or so years I’ve been in the business. It seems they come along every 10 years. We have Swiss Skydiver in 2020. In 2010, we had Beautician. She ran second in the Breeders’ Cup Juvenile Fillies. She was beaten three-quarters of a length and she came back with three quarters of her shoes. We think if there was a make good, we would win the next time.

PEDULLA: What can you tell me about your experience in breeding horses?

CALLAHAN: It’s been fun. Breeding horses, if it’s managed carefully, can be profitable. If you take a five-year period as a measurement, you lose some money in one of the five years, you break even in one and then three of the five years you make money. You can make modest amounts, middle-market amounts or you can hit it over the fence, or against the wall, anyway. Breeding horses takes a lot of my time. You need to do a lot of analysis.

PEDULLA: What can you tell me about the purchase of Swiss Skydiver?

Kenny McPeek (Coady Photography)

CALLAHAN: Kenny [McPeek] knows that I take a chance. He will give me a horse that he generally finds in the final few books of the Keeneland sale. When he came across this horse we’ve come to know as Swiss Skydiver, he presented her as a very handsome horse, a big hip. He’s big on the hip. I don’t know much about the physique of a horse, but he knows a lot. He said, ‘Peter, this one is going to be right up your alley. She will probably go for 50 grand.’ I said, ‘Let’s buy her.’ 

PEDULLA: Did the relatively low price concern you at all?

CALLAHAN: I don’t know why more people are not interested in going up and down the hills of Keeneland for the second-to-last book. A lot of people won’t buy an inexpensive horse. They think there is something intrinsically wrong. They feel if they spend more money, they will get a better horse. That is largely true, but it’s not always true. You can find a real good horse at the other end of the spectrum. In the years ahead, we’ll continue to listen to Kenny. I call him Kenny ‘Pull One Out of a Hat.’

PEDULLA: When did you start thinking Swiss Skydiver might be special? 

CALLAHAN: We didn’t start cranking on her until the middle of September or October. Kenny reported to me and said, ‘Peter, this girl is really fast. I’m not sure how far she can go. She should be able to go far with her pedigree.’

PEDULLA: What led you to enter her in the Blue Grass?

CALLAHAN: Kenny began building a case that we would be better off entering the Blue Grass than the Ashland [Stakes]. He didn’t think the crop of colts so far this year has been overwhelming. He said the Ashland would be tougher than the Blue Grass, and he was right because I did my own analysis. Before I made the final decision, I conferred with my three daughters and four granddaughters and they all said, ‘Let’s go beat the boys!’

PEDULLA: Does this kind of decision fit your personality?

CALLAHAN: Oh, yes. I was always a little crazy.

PEDULLA: Would you seriously consider the Derby if she wins the Blue Grass?

CALLAHAN: Well, if she won today and got points, there is no question we would consider the Derby. Yes, it’s very much in play. It’s one of the motivators to take on the boys today.