This could finally be the year Michael Iavarone gets his Pegasus Day victory. Seven years after returning to the Sport of Kings, Iavarone, arguably one of the most polarizing figures in racing, will start nine horses Jan. 27 on Gulfstream Park's biggest day, with two live contenders in O'Connor and Master Piece. Both Chilean-breds will enter their respective races in the Pegasus World Cup Invitational Stakes (G1) and Pegasus World Cup Turf Invitational Stakes (G1T) in the top shape of their careers.
Iavarone, best known as the owner of 2008 Kentucky Derby (G1) and Preakness Stakes (G1) hero Big Brown and a host of star-studded athletes running under the late IEAH Stables banner, spoke with BloodHorse MarketWatch about breaking his Pegasus Day curse, his passion for the game, and his special relationship with Master Piece's trainer, his old friend Rick Dutrow Jr.
BloodHorse: You’ve had horses running on Pegasus Day since you re-entered the sport in 2017. What does a win on Pegasus Day mean to you?
Michael Iavarone: Not only am I running a horse in the Pegasus and Pegasus Turf, I’m running nine horses that day total and have one in all the stakes. I just want to have a day where I can get all my friends – I think we’re going to have 40 people—in the winner’s circle on Pegasus Day. I don’t even care what race it is, I just need to break this losing streak. I think I’m 0-for-20 or something like that on Pegasus Day. I just feel like this year I’m coming in with better horses, though the horses we're up against are also tougher. Last year it was ironic; I had a horse that ran second in a 1x allowance race on the grass to a horse that was Up to the Mark, who’s probably going to be grass champion. I caught him in a 1x. That’s the way it's been.
Either way, though, it's our favorite day of the year.
BH: How would you compare winning the Pegasus World Cup with the Kentucky Derby?
MI: The Derby is the Derby. The Derby is every owner’s dream. If you’ve won it once, you want to win it twice. It’s the race that everybody who spends billions of dollars in this game wants to win.
But like I said, the Pegasus has now become something of an enigma for me. It's a race I want to win and I want to jump that hurdle more than the second Derby hurdle. My wife and I feel like we’ve accomplished so much in racing, but in this race, we are never close in the Pegasus (or Pegasus Turf). We don’t even get a minute of excitement our horses start in the back and finish in the back.
BH: What made you want to re-enter the sport in 2017?
MI: When I left the sport, I had decided that syndicates were not the way to go for me. It required too many decisions for the best interest of everyone else but the horse. You have 30, 50, sometimes more people invested in the horse. I told myself that if I ever got back into the game I would own the horses myself or own them with maybe one or two people that were very knowledgeable and would put the best interests of the horse first.
In 2017 I said to my wife (Jules) I think it's time. It's something my wife and I have always had a passion for. I wanted to do it for something to enjoy, I didn't want to make a massive financial contribution. I don't do horses for a living, I'm an asset manager for a living. We took it on as a hobby, though it's quickly grown to 17 horses. If it's in your blood, it's in your blood.
BH: You'll have two contenders, one in the Pegasus and one in the Pegasus Turf, that you purchased privately as older horses. How did you come to find and acquire O'Connor?
MI: Last year I bought into the horse after he won his North American debut. He was very impressive and ran a fast speed figure. (Trainer) Saffie (Joseph Jr.) had told me he was really high on the horse, higher than on anyone else he had in the barn. At the time he had White Abarrio and Skippylongstocking targeting the race as well. So I partnered up with Fernando Vine who brought the horse over from Chile.
BH: O'Connor finished 11th in last year's Pegasus. What was behind the decision to enter him in this year's race? Do you think he's a different horse now than he was last year?
MI: We weren't on the initial list of Pegasus invites last year and then he got on the second list. He drew post 12, so I was not incredibly optimistic going in, especially coming after a dull race (when fourth in the Harlan's Holiday). He ran surprisingly even worse than I anticipated. He was not engaged at any point in the race.
After his race (in the Ghostzapper Stakes,G3) we found out he had a bit of an entrapment going on. We were excited—finding this out—not by him having an issue but because we found something that could be getting in the way of him being able to compete at his best. We had the procedure (throat surgery) done and gave him a ton of time to recover.
We brought him back in West Virginia (in the West Virginia Governor's Stakes, G3) and he missed the break but showed interest late, and then we ran him back in a very difficult spot with an outside post in the Charles Town Classic (G2). He really started to show signs that he was coming into form there. He put in a really good late run to get second in that race.
We then found that race at Keeneland (Lafayette Stakes, G2), and that's when I think everything started coming together. He broke with the field, took a lot of kickback, ran a wide race, and finished strong. That's when we knew where we wanted to be with him.
His last race in the Harlan's Holiday I thought that was the best race he ever ran. Maybe not numbers-wise, but it's very difficult to pass horses on the inside like that here (at Gulfstream).
BH: Despite facing horses like National Treasure, Hoist the Gold, and Skippylongstocking, what do you think of his chances in the Pegasus?
MI: I think he's a very, very live horse coming into this spot. I think he's going to love the pace setup he's going to get. There will be plenty of speed in there for him and he can sit seven, eight lengths back. If we get a good draw (he's in post 2), I think he's proven he can rate kindly from any position. Saffie is very high on him and we think we're back to where we were on Day 1 after he first won that allowance race (in October 2022). He's set up now to run the biggest race of his life.
If we get a good trip, I don't see any reason why he can't be right there.
BH: If O'Connor were to win the Pegasus, would you consider sending him to the Middle East to compete in the Saudi Cup or Dubai World Cup?
MI: I think we've always had that (the Dubai World Cup) in the back of our head. I like that it's 1 1/4 miles; I think the further the better for him. He has to show us he deserves that and this is far from an easy race, so if he shows us he belongs with these horses, the Saudi Cup or Dubai would definitely be something we'd target.
BH: O'Connor and Master Piece were both bred in Chile. What has drawn you to two Chilean-bred horses?
MI: I don't know what it is, but these Chilean horses are made like machines. Their legs are so sound and even at their older ages they just don't seem to have all the physical issues some of my younger horses bred here have. There's something about these horses, they don't miss a beat.
BH: Master Piece is trained by Rick Dutrow Jr. You guys partnered up to win several grade 1 races with him in the past, including the Derby and Preakness. How special would it be to win a grade 1 again with Dutrow now a decade later?
MI: Everything I do with Rick is special. We have a special relationship. We've stayed friends through the whole thing. We all have our opinions on what Rick is and what Rick isn't. But the one thing I can tell you is that horses love being around him. Master Piece has thrived in his barn. It took Rick a while to figure him out but he's made him into a better horse. I think of all the races on Pegasus Day, that's the toughest race, but Master Piece is still my best shot at winning.
Rick hasn't been this high on the horse since he's had him. We just think he's going to move way up off the Red Smith. He's going to come running like a machine at the end of this race.
I've always loved those kind of horses (closers). My wife and I are big NASCAR fans and we like when the drivers are closing down the leaders, not being chased. I love a horse that comes from behind.
