Well, for starters, his horse Nyquist -- the 10-3 favorite to win Saturday's Kentucky Derby -- is named after a player on his favorite team, the Detroit Red Wings.
The 60-year-old Reddam, who made his fortune launching two lending businesses, grew up in Windsor, Ontario, just across the border from Detroit where his mother, a team secretary, would bring home Red Wings tickets and apparel.
"That's how I really got hooked," Reddam tells CNN, adding that he caught 75 of the Red Wings' 82 games on TV this season. He even got to sip champagne from the Stanley Cup when Detroit won the title in 2002.
"That was almost as big a thrill as winning the Derby a few years ago," he says, referring to his 2012 Kentucky Derby winner I'll Have Another, who went on to take the Preakness, before pulling out of the Belmont Stakes a race shy of the Triple Crown.
Reddam will be reunited with the hallowed Stanley Cup when it makes its way to Nyquist's stable
on Saturday for some pre-Derby good karma. One person who won't be attending, however, is Gustav Nyquist himself.
The right winger, who has yet to meet Reddam, was invited to the owner's box via text message, but had to pass after being called up to Sweden's world championship squad.
Although Reddam is certainly a fan of the Swede -- "I really like him as a player. He's very classy and a very good stick handler" -- he confesses that the name came about as a way to annoy his friend Colorado Avalanche defenseman Erick Johnson, who vowed never to join the Red Wings.
Nevertheless, Johnson, who sometimes co-invests in Reddam's horses, wanted a piece of the action once Nyquist blossomed into a world class sprinter. His 7-0 record includes a convincing win over second-favorite Mohaymen.
"I said: 'Sorry buddy that's not happening,'" laughs Reddam, who, despite his PhD in philosophy, is a stickler for superstition.
"Listen, you said you'd never sign with them, so you're not owning a horse with a Red Wing name." Another colt at Reddam Racing that is off-limits: Mrazek, named after the Red Wings' Czech goalie.
Bringing business sense to the track
After starting out as a college professor, Reddam founded two highly lucrative businesses that delivered high interest loans, a practice which has landed his company CashCall in hot water
"I'm not saying these loans are for everybody," Reddam told the New York Times in 2012. "You should think of what you're doing."
There is no equivocation, however, when it comes to operating his racing stable: "It absolutely has to be a business otherwise your passion will die off and then you'll go broke."
Moreover, he says that earning riches off the racetrack can burden newcomers into thinking they know what they're doing, when in fact they don't.
"Having knowledge in some other business, or revolutionizing some other business ... it doesn't follow that they are going to have success in this business," Reddam clarifies, adding that breeders in the Bluegrass state can give the impression that they can be easily bamboozled, though the opposite is often true.
"People think they're going to come and take advantage of them, but they've got it completely backwards," he warns. "They think: 'I'm going to buy the best; that's how I'm going to beat everybody,' and within two years they're gone because they have lost a fortune."
Spending big on horses is "a universal bust"
Although his two favorite sports are wildly popular in his native Canada, horse racing is in no way similar to hockey from a business point of view, says Reddam.
"If you bought a mainstream sports franchise -- generally speaking -- even if you are terrible at running it you'd have to make money, because the value of any team in the league would have greatly appreciated," he says, adding that the age-old practice of spending big on prospects does not translate well on the racetrack.
"In horse racing that is almost universally going to be a bust ... it doesn't work that way at all."
Instead, Reddam employs the services of "talent scouts" who tip him off to prospects they believe offer good value. Reddam will then "evaluate the evaluators" to make a decision.
The process has been paying off in spades.
Last year's $400,000 purchase of Nyquist has already reaped $2.3 million in prize money -- not counting his potential share of Saturday's $2 million purse.
The purchase was made via horse broker Dennis O'Neill, brother of Nyquist's trainer Doug O'Neill -- who also happens to have trained I'll Have Another.
Back in 2012, Reddam took some heat for employing Doug O'Neill fresh off an announced suspension by California racing authorities for a drug violation.
But ignoring the critics has arguably proved to be the right call.
I'll Have Another was purchased for just $35,000 and ended his career with over $2.6 million in earnings before being sold to a stud farm.
Learning to deflect criticism and focus on the future, it turns out, is a discipline in line with Reddam's teachings as a former philosophy professor.
"Philosophy is really about possibility," he says, "When you buy horses, you usually buy them before they ever run, so you're imagining what this horse could be.
"So from that sense it's been very helpful to have a (vision) of what you're hoping for long term when the horse is a baby."
Despite all his rational, Reddam still leans on pure superstition when it comes to race day. For starters, if you happen to walk by him at Churchill Downs, never say 'I'll see you in the winner's circle.'"
"That is the kiss of death," he says. "Whenever anyone's said that to me who is kind of new to the races, or coming as a visitor, or whatever (I think), 'Ooh, You just didn't say that to me did you?'"
Wishing each other good luck, however, is fine -- even if it's fake.
"Actually, in horse racing all the (competitors) wish each other good luck," he says. "And I would say 98% of the time that's completely insincere.
"They definitely want to beat you, and, they don't want your horse to get hurt, but they want you to have bad luck as far as the race goes."
One thing that's legit: Reddam would relish the chance to drink out of the Stanley Cup again -- this time as part of the winning team, not simply a fan.
He may, in fact, even have some company.
"I don't know if there will be any pictures of Nyquist drinking out of it or not," he ponders.