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Double Derby Winner Paul Reddam, ‘The Luckiest Guy in Racing’

An exclusive excerpt from Lenny Shulman's new book 'Head To Head: Conversations with a Generation of Horse Racing Legends'.

Paul Reddam (center), wife Zillah and jockey Mario Gutierrez in the paddock at the Breeders Cup 2016. (Doug O'Neill Racing photo)

By: Lenny Shulman | June 21, 2021

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you're listening to an article from canadian thoroughbred.com. double derby winner paul reddam, ‘the luckiest guy in racing’ by: lenny shulman. as a former university logistics instructor, paul reddam would have realized the odds against winning the kentucky derby once, let alone twice. but that didn’t stop the canadian-born reddam from switching to thoroughbreds after an initial dive into the harness racing world. after settling in california and developing and then selling a popular mortgage company, reddam stepped up his involvement in horses, yet has managed to do more with less. playing in the middle of the market, and in concert with trainer doug o’neill and his brother, bloodstock agent dennis o’neill, reddam has reached the mountaintop twice, when i’ll have another won the 2012 derby and preakness, and nyquist turned the derby trick in 2016. our first interview came nearly a decade before his first derby victory. his story was updated, of course, after his success in louisville. 2003: interviewed at santa anita park, california. lenny shulman: it’s well known you’re a fan of hockey and the detroit red wings, but how did you become a fan of horse racing? advertisement scroll to continue with content paul reddam: traditionally, canadians have always been involved in harness racing. where i’m from—in ontario—there’s a track every fifty miles. so i grew up on the harness races. in high school, my best friend was a groom at windsor raceway, our home track just across the border from detroit. he used to bug me to go out, and i finally did and caught the fever. the first time i was even at a thoroughbred race was after i moved out to california in 1979. out of curiosity i went to santa anita at the time when spectacular bid was a four-year-old and dominating the big races. i still have a vivid memory of the big ’cap—there were only four horses—bid, flying paster, relaunch, and a horse i don’t remember. i bet every dime i had on a bid-flying paster exacta, and down the backside relaunch was way out in front, and i said, “oh, shit, i’m going to be broke.” but sure enough at the wire it was the bid by five or six and then paster by ten. i wasn’t used to the way thoroughbred races went. but that was a powerful experience. ls: how did you get into ownership? pr: i had gotten a scholarship from the canadian government to work on my phd at usc, and i was teaching logic there. usc waived my tuition, so i had extra money and bought a standardbred with my old high school friend. he raced back in canada. eventually i talked my friend into moving here. i had a student whose husband was a doctor, and i convinced him and some of his doctor pals to cough up some money, and we bought a few standardbreds who raced at hollywood park. ls: and the move to thoroughbreds? pr: i had a few claimers in the nineties, and then decided to get back into it around 2000. i asked my attorney to interview some trainers, and he came back and said wally dollase’s son craig seemed enthusiastic. he had won the breeders’ cup sprint in 1998 with reraise, so he seemed like a good choice. he earned my trust by going to a sale in ocala with my ok to buy some horses, and he didn’t buy anything. and i thought, “how unusual is this?” i still hadn’t met him, and normally if you told somebody you’d never met to go buy a horse or two, they’d come back with three or four. he bought one horse at the keeneland sale that year—zillah the hun, who ended up winning a graded stakes. i thought that was pretty good on craig’s part. then he bought swept overboard out of the 505 dispersal, and that turned out well. ls: did you have a business plan for the thoroughbreds? pr: the answer there would be “no.” there’s no grand plan. you hear of the 80/20 rule in business, that 80 percent of the production is done by 20 percent of the people? in thoroughbreds, it’s the 95/5 rule. ninety-five percent of the people will lose, and 5 percent will get all the money. i think that we’ve been very lucky. my goal was really to have a good time and not blow too much money. when we sold swept overboard to japan, that pretty much paid for a lot of purchases. it’s pretty clear to me that you have to make your money through the residual interest in the horse. meaning that the real money isn’t purse money, it’s in the breeding side or sale of breeding stock. in buying horses now, i ask what the potential is for the horse. and that doesn’t mean buying every storm cat at the sale. it’s more like, “if this athlete pans out, is there an upside here?”. with fillies, you need to decide whether you want to get into the breeding end. we have elloluv now, a graded stakes winner, and we haven’t decided yet, but the temptation would be to sell her. i’m going to get heat for that from my wife. ls: how do you reconcile your background in academic philosophy with being in the horse business? pr: that’s easy. logic is about possibility. when you buy a racehorse, you’re always dreaming about the possibilities. that goes for everyone in this game. not what is, but what could be. everybody who buys a horse has a dream about the kentucky derby or winning something big. the philosopher closest to the racing game would be the british empiricist david hume, who wrote a lot about causality. you assume a lot of things in life; we go through presuppositions about everything, but it doesn’t need to be that way—things can turn out in all different ways. turn back the clock to when you were a kid—would you think you’d be writing an article for the bloodhorse on santa anita derby day? you just don’t know. ls: you are aggressive in placing your horses. pr: yes, i do get involved in twisting craig’s arm to put a horse in a stakes race that he doesn’t want to. swept overboard in the met mile, elloluv in the hollywood starlet, and logician in the san felipe were all examples that worked out well. he’s in a difficult spot because he doesn’t want to tick off a major owner, but at the same time he wants to win races. and usually, when an owner gets too involved, it’s a bad thing for the management of the stable. but my thought is, “what’s the downside to running in a stakes race?” you miss an allowance race where you’d be odds-on and win thirty thousand dollars in purse money. you can always come back and run in that allowance race if it doesn’t pan out, so if that’s where you fit, you’ll get there eventually. ls: you’re a risk-taker. pr: the point is, if you think the horse is good enough and you’re on a certain path, there could be lots of reasons that he throws a clunker. if i’m confident in something and it didn’t turn out, i make the play again. back in the eighties i had a bookie. i bet my horse heavily at a harness track and was convinced he couldn’t lose. he went off as the chalk and finished fifth. i owed the guy six thousand dollars and didn’t have the money to pay him. i told him i’d meet him at the track saturday night to pay him, and also told him the horse was back in, and i wanted to bet a thousand across on him. he goes off at 10–1 and wins. i meet the guy and say, “well, i guess i don’t need to pay you now since you owe me.”. ls: you took a risk with cheesy commercials—i remember you being on tv—for your mortgage business. pr: like a lot of things, a lot of it was luck. often, the best ideas are really simple. i’d been in the mortgage business for a number of years, and it had been boom-and-bust. i didn’t understand why somebody didn’t go on television and give out the rates like a weather report: “today’s rate is this. if you want it, call us up.” i bounced it off some guys from ge capital. and they looked at me like i was nuts. call me stupid, call me naïve, but i think people want to get the straight stuff blared right at them. i gathered up what little money i had, started ditech, and did a radio spot with today’s rate. the first day there were six calls, and i figured i was in trouble. then the next day the phone rang more, and soon it blasted off like a rocket. then i’m driving down the freeway and see a billboard from a radio station saying, “this is the song and artist we’re playing right now.” and i thought, “why can’t you do that for interest rates? today’s rate is such and such.” so i bought a couple of billboards, and it exploded. then we ran tv spots during the o.j. trial on a local channel. the air time wasn’t that expensive, and everyone was glued to that thing in the summer of ’95. as far as rating my performance, steven spielberg hasn’t called with any offers. ls: you’ve bought two-year-olds, runners from europe, horses out of dispersals. pr: the one place we haven’t bought is the most common place—yearling sales. i believe they’re the riskiest sales, other than buying weanlings, i guess. when you look at the prices at yearling sales—which are all over the map—and you consider, “what are the odds this horse is going to make it to the races?” it’s pretty low. if you buy at a two-year-old in-training sale, you’re still paying up, but at least you’ve seen him move under tack. obviously, you’re taking a huge risk there, too, but we’ve been fairly lucky at that so far. elloluv is paying for everybody else. you have a hope and a plan for every one you buy, but sometimes they don’t come anywhere near that. we bought a horse after he won two legs of the triple crown in argentina, and he got beat twenty-eight lengths in the uae derby last week. so now, we don’t know what we bought. we paid a lot of money for castle gandolfo, thinking if he wins a graded stakes, he’s stallion material—he’s by gone west and his dam is a half sister to el gran senor. but so far, he’s been a dud. you don’t know. you have a secret hope that things are going to turn out well. it’s a game of high highs and low lows, and more low lows than high highs. ls: later today you have elloluv running in the santa anita oaks and logician in the santa anita derby. pr: she’s done enough already to go to the kentucky oaks [elloluv would finish fourth in the kentucky oaks], so we’re going to go to louisville anyway, and we’d like to take logician to the derby. but if he doesn’t go forward today, we’ll say we tried, and so it goes. almost everyone who gets interviewed says the only way they’d go to the kentucky derby is if they think their horse has a legitimate shot, and i think half those people are lying. if the horse gets in, they’re going. my honest answer is if he qualifies, we’re going with him. everything changes quickly, and you just don’t know. if he races badly today, you don’t want to go on and make a fool of yourself. [logician did not race in the kentucky derby.]. if someone tells you the kentucky derby doesn’t mean that much to them, they’re all liars. i was thinking that if we ever got in the derby and won, that would be the time to get out of the game. you see people who win it and then spend millions and millions trying to repeat the experience. and it’s not going to happen. you hit the top and that’s it. 2012: immediately after winning the kentucky derby with i’ll have another, churchill downs, louisville. lenny shulman: were you confident heading into the race? paul reddam: well, with ten most wanted [who finished ninth in 2003] i was highly confident, but i’ve learned to be less confident just on the probability aspect that there’s a 95 percent chance you’ll lose. to me, this horse is the real deal, and i thought he was going to run the race of his life. the question was, “is he good enough?” to win the race, you’ve got to have the right, lucky trip. we were in the exact position we talked about wanting to be in. i looked at the tote board and the half went in:45 and change and he was sitting off it, and i thought, “man, did i dream this or what?”. and then, truthfully, i lost sight of him. i heard the call that bodemeister was in the clear. but i know the way our kid [mario gutierrez] rides—just when it looks like he’s waiting too long, he goes. so when i saw someone coming, i said, “is that him?” and it was, and then i saw we were going to win, and then i don’t know what happened. it all went according to plan, and how often does that happen? like, almost never. i might be dreaming. who knows? i’m just so excited for the whole team. i don’t know that anything could be bigger than winning the kentucky derby. ls: is this a bigger thrill than drinking from the stanley cup when the red wings won it in 2002? pr: yes, this is above drinking from the cup, are you kidding me? 2016: immediately after winning the kentucky derby with nyquist, churchill downs, louisville. lenny shulman: how can you explain winning two kentucky derbys? paul reddam: well, one of your colleagues [steve haskin] told me years ago i was the luckiest guy in racing. i think that’s how i’d explain it. i’m just very lucky to be with these guys [trainer doug o’neill and bloodstock agent dennis o’neill]. it’s as simple as that, really. *** lenny shulman is an award-winning tv and film writer, journalist, editor and author living in versailles, kentucky.’ head to head: conversations with a generation of horse racing legends is available to purchase here. reprinted with permission from the university press of kentucky. &&>

As a former university logistics instructor, Paul Reddam would have realized the odds against winning the Kentucky Derby once, let alone twice. But that didn’t stop the Canadian-born Reddam from switching to Thoroughbreds after an initial dive into the harness racing world.

After settling in California and developing and then selling a popular mortgage company, Reddam stepped up his involvement in horses, yet has managed to do more with less. Playing in the middle of the market, and in concert with trainer Doug O’Neill and his brother, bloodstock agent Dennis O’Neill, Reddam has reached the mountaintop twice, when I’ll Have Another won the 2012 Derby and Preakness, and Nyquist turned the Derby trick in 2016. Our first interview came nearly a decade before his first Derby victory. His story was updated, of course, after his success in Louisville.

2003: Interviewed at Santa Anita Park, California

Lenny Shulman: It’s well known you’re a fan of hockey and the Detroit Red Wings, but how did you become a fan of horse racing?

Scroll to continue with content

Paul Reddam: Traditionally, Canadians have always been involved in harness racing. Where I’m from—in Ontario—there’s a track every fifty miles. So I grew up on the harness races. In high school, my best friend was a groom at Windsor Raceway, our home track just across the border from Detroit. He used to bug me to go out, and I finally did and caught the fever.

The first time I was even at a Thoroughbred race was after I moved out to California in 1979. Out of curiosity I went to Santa Anita at the time when Spectacular Bid was a four-year-old and dominating the big races. I still have a vivid memory of the Big ’Cap—there were only four horses—Bid, Flying Paster, Relaunch, and a horse I don’t remember. I bet every dime I had on a Bid-Flying Paster exacta, and down the backside Relaunch was way out in front, and I said, “Oh, shit, I’m going to be broke.” But sure enough at the wire it was the Bid by five or six and then Paster by ten. I wasn’t used to the way Thoroughbred races went. But that was a powerful experience.

LS: How did you get into ownership?

PR: I had gotten a scholarship from the Canadian government to work on my PhD at USC, and I was teaching logic there. USC waived my tuition, so I had extra money and bought a Standardbred with my old high school friend. He raced back in Canada. Eventually I talked my friend into moving here. I had a student whose husband was a doctor, and I convinced him and some of his doctor pals to cough up some money, and we bought a few Standardbreds who raced at Hollywood Park.

LS: And the move to Thoroughbreds?

PR: I had a few claimers in the nineties, and then decided to get back into it around 2000. I asked my attorney to interview some trainers, and he came back and said Wally Dollase’s son Craig seemed enthusiastic. He had won the Breeders’ Cup Sprint in 1998 with Reraise, so he seemed like a good choice. He earned my trust by going to a sale in Ocala with my OK to buy some horses, and he didn’t buy anything. And I thought, “How unusual is this?” I still hadn’t met him, and normally if you told somebody you’d never met to go buy a horse or two, they’d come back with three or four.

He bought one horse at the Keeneland sale that year—Zillah the Hun, who ended up winning a graded stakes. I thought that was pretty good on Craig’s part. Then he bought Swept Overboard out of the 505 dispersal, and that turned out well.

LS: Did you have a business plan for the Thoroughbreds?

PR: The answer there would be “No.” There’s no grand plan. You hear of the 80/20 rule in business, that 80 percent of the production is done by 20 percent of the people? In Thoroughbreds, it’s the 95/5 rule. Ninety-five percent of the people will lose, and 5 percent will get all the money. I think that we’ve been very lucky. My goal was really to have a good time and not blow too much money. When we sold Swept Overboard to Japan, that pretty much paid for a lot of purchases.

It’s pretty clear to me that you have to make your money through the residual interest in the horse. Meaning that the real money isn’t purse money, it’s in the breeding side or sale of breeding stock. In buying horses now, I ask what the potential is for the horse. And that doesn’t mean buying every Storm Cat at the sale. It’s more like, “If this athlete pans out, is there an upside here?”

With fillies, you need to decide whether you want to get into the breeding end. We have Elloluv now, a graded stakes winner, and we haven’t decided yet, but the temptation would be to sell her. I’m going to get heat for that from my wife.

LS: How do you reconcile your background in academic philosophy with being in the horse business?

PR: That’s easy. Logic is about possibility. When you buy a racehorse, you’re always dreaming about the possibilities. That goes for everyone in this game. Not what is, but what could be. Everybody who buys a horse has a dream about the Kentucky Derby or winning something big. The philosopher closest to the racing game would be the British empiricist David Hume, who wrote a lot about causality. You assume a lot of things in life; we go through presuppositions about everything, but it doesn’t need to be that way—things can turn out in all different ways. Turn back the clock to when you were a kid—would you think you’d be writing an article for the
Bloodhorse on Santa Anita Derby day? You just don’t know.

LS: You are aggressive in placing your horses.

PR: Yes, I do get involved in twisting Craig’s arm to put a horse in a stakes race that he doesn’t want to. Swept Overboard in the Met Mile, Elloluv in the Hollywood Starlet, and Logician in the San Felipe were all examples that worked out well. He’s in a difficult spot because he doesn’t want to tick off a major owner, but at the same time he wants to win races. And usually, when an owner gets too involved, it’s a bad thing for the management of the stable. But my thought is, “What’s the downside to running in a stakes race?” You miss an allowance race where you’d be odds-on and win thirty thousand dollars in purse money. You can always come back and run in that allowance race if it doesn’t pan out, so if that’s where you fit, you’ll get there eventually.

LS: You’re a risk-taker.

PR: The point is, if you think the horse is good enough and you’re on a certain path, there could be lots of reasons that he throws a clunker. If I’m confident in something and it didn’t turn out, I make the play again. Back in the eighties I had a bookie. I bet my horse heavily at a harness track and was convinced he couldn’t lose. He went off as the chalk and finished fifth. I owed the guy six thousand dollars and didn’t have the money to pay him. I told him I’d meet him at the track Saturday night to pay him, and also told him the horse was back in, and I wanted to bet a thousand across on him. He goes off at 10–1 and wins. I meet the guy and say, “Well, I guess I don’t need to pay you now since you owe me.”

LS: You took a risk with cheesy commercials—I remember you being on TV—for your mortgage business.

PR: Like a lot of things, a lot of it was luck. Often, the best ideas are really simple. I’d been in the mortgage business for a number of years, and it had been boom-and-bust. I didn’t understand why somebody didn’t go on television and give out the rates like a weather report: “Today’s rate is this. If you want it, call us up.” I bounced it off some guys from GE Capital. and they looked at me like I was nuts.

Call me stupid, call me naïve, but I think people want to get the straight stuff blared right at them. I gathered up what little money I had, started DiTech, and did a radio spot with today’s rate. The first day there were six calls, and I figured I was in trouble. Then the next day the phone rang more, and soon it blasted off like a rocket. Then I’m driving down the freeway and see a billboard from a radio station saying, “This is the song and artist we’re playing right now.” And I thought, “Why can’t you do that for interest rates? Today’s rate is such and such.” So I bought a couple of billboards, and it exploded.

Then we ran TV spots during the O.J. trial on a local channel. The air time wasn’t that expensive, and everyone was glued to that thing in the summer of ’95.

As far as rating my performance, Steven Spielberg hasn’t called with any offers.

LS: You’ve bought two-year-olds, runners from Europe, horses out of dispersals . . .

PR: The one place we haven’t bought is the most common place—yearling sales. I believe they’re the riskiest sales, other than buying weanlings, I guess. When you look at the prices at yearling sales—which are all over the map—and you consider, “What are the odds this horse is going to make it to the races?” It’s pretty low. If you buy at a two-year-old in-training sale, you’re still paying up, but at least you’ve seen him move under tack. Obviously, you’re taking a huge risk there, too, but we’ve been fairly lucky at that so far. Elloluv is paying for everybody else.

You have a hope and a plan for every one you buy, but sometimes they don’t come anywhere near that. We bought a horse after he won two legs of the Triple Crown in Argentina, and he got beat twenty-eight lengths in the UAE Derby last week. So now, we don’t know what we bought. We paid a lot of money for Castle Gandolfo, thinking if he wins a graded stakes, he’s stallion material—he’s by Gone West and his dam is a half sister to El Gran Senor. But so far, he’s been a dud. You don’t know. You have a secret hope that things are going to turn out well. It’s a game of high highs and low lows, and more low lows than high highs.

LS: Later today you have Elloluv running in the Santa Anita Oaks and Logician in the Santa Anita Derby.

PR: She’s done enough already to go to the Kentucky Oaks [Elloluv would finish fourth in the Kentucky Oaks], so we’re going to go to Louisville anyway, and we’d like to take Logician to the Derby. But if he doesn’t go forward today, we’ll say we tried, and so it goes.

Almost everyone who gets interviewed says the only way they’d go to the Kentucky Derby is if they think their horse has a legitimate shot, and I think half those people are lying. If the horse gets in, they’re going. My honest answer is if he qualifies, we’re going with him. Everything changes quickly, and you just don’t know. If he races badly today, you don’t want to go on and make a fool of yourself. [Logician did not race in the Kentucky Derby.]

If someone tells you the Kentucky Derby doesn’t mean that much to them, they’re all liars. I was thinking that if we ever got in the Derby and won, that would be the time to get out of the game. You see people who win it and then spend millions and millions trying to repeat the experience. And it’s not going to happen. You hit the top and that’s it.

2012: Immediately after winning the Kentucky Derby with I’ll Have Another, Churchill Downs, Louisville

Lenny Shulman: Were you confident heading into the race?

Paul Reddam: Well, with Ten Most Wanted [who finished ninth in 2003] I was highly confident, but I’ve learned to be less confident just on the probability aspect that there’s a 95 percent chance you’ll lose. To me, this horse is the real deal, and I thought he was going to run the race of his life. The question was, “Is he good enough?” To win the race, you’ve got to have the right, lucky trip. We were in the exact position we talked about wanting to be in. I looked at the tote board and the half went in :45 and change and he was sitting off it, and I thought, “Man, did I dream this or what?”

And then, truthfully, I lost sight of him. I heard the call that Bodemeister was in the clear. But I know the way our kid [Mario Gutierrez] rides—just when it looks like he’s waiting too long, he goes. So when I saw someone coming, I said, “Is that him?” And it was, and then I saw we were going to win, and then I don’t know what happened.

It all went according to plan, and how often does that happen? Like, almost never. I might be dreaming. Who knows? I’m just so excited for the whole team. I don’t know that anything could be bigger than winning the Kentucky Derby.

LS: Is this a bigger thrill than drinking from the Stanley Cup when the Red Wings won it in 2002?

PR: Yes, this is above drinking from the Cup, are you kidding me?

Shulman’s new book features 37 interviews with industry legends, owners, trainers, veterinarians, and celebrities.

2016: Immediately after winning the Kentucky Derby with Nyquist, Churchill Downs, Louisville

Lenny Shulman: How can you explain winning two Kentucky Derbys?

Paul Reddam: Well, one of your colleagues [Steve Haskin] told me years ago I was the luckiest guy in racing. I think that’s how I’d explain it. I’m just very lucky to be with these guys [trainer Doug O’Neill and bloodstock agent Dennis O’Neill]. It’s as simple as that, really.

***
Lenny Shulman is an award-winning TV and film writer, journalist, editor and author living in Versailles, Kentucky.’ Head To Head: Conversations with a Generation of Horse Racing Legends is available to purchase here.

Reprinted with permission from the University Press of Kentucky.