He spent millions collecting the rarest sneakers and cars on earth. Now he’s over it.

His wife was out wakeboarding with the kids, he was sitting at his computer, and suddenly he’d bought nearly 100 high-value shoes. Nadal recalled telling his wife simply, “I bought some shoes," as if he was describing buying a lone pair of Nikes from Zappos.

Days later, in a private sale, the financier, now 65, bought a Nike prototype sneaker, the waffle-soled “Moon Shoe" from 1972, for $437,500, a then-record-shattering sum for a single pair of sneakers. That 100-pair sale was Sotheby’s first ever sneaker auction. And Nadal took home the entire lot.

As Nadal, the founder of Peerage Capital, an investment firm with holdings in the real estate, self-storage and wealth management sectors, humbly said looking back, “It became the beginning of a trend that sneakers became walkable art."

In the span of a week, this kooky middle-aged investor became perhaps the most unexpected sneaker collector in the world. He put them in a Canadian museum along with an array of more than 160 cars he’d collected over the years.

Now Nadal has decided to cut short his reign as a sneaker collecting kingpin. On June 1st, he’ll be auctioning off the bulk of his shoe collection.

Around 750 pairs will be up for grabs at R.M. Sotheby’s auction house. That includes roughly 500 pairs of Air Jordans (some from as far back as the mid-’80s) and shoes signed by OJ Simpson, Tom Brady, Steph Curry and Joel Embiid.

There will also be two pairs of Nike’s rare Air Mag shoes and a self-lacing sneaker that was designed to look like the futuristic sneakers Marty McFly wore in “Back to the Future." The entire collection is estimated to notch well over $2 million, according to R.M. Sotheby’s.

144 of his cars and motorcycles are being auctioned off, too, including an electric car from 1913 and various high-value Ferraris, McLarens and Lamborghinis. That assortment is estimated to sell for in excess of $60 million, though R.M. Sotheby’s is still finalizing the assortment and estimates for the sale.

While some analysts have expected the high-end sneaker auction market to cool after a pandemic buying bonanza, recent sales have continued to grab headlines. In early February, a series of six sneakers that Michael Jordan wore to win his six NBA championships sold at Sotheby’s for a record-setting $8 million.

The financier’s dream would be for someone to purchase the entire collection together, as he did with his 100 initial shoes, but Nadal admitted that “the probability of that is not that high."

Nadal first made his fortune as the founder and long-time CEO of MDC Partners, owner of a variety of advertising agencies. Nadal stepped down from MDC in 2015 amid a Securities and Exchange Commission investigation into his expenses and other matters. He agreed to pay MDC $8.6 million for reimbursed expenses at the time.

Nadal, who said he had been the “first person to ever own a new car in my family," got into collecting in 2000, when he purchased his first high-end auto. More cars would follow, with prices eventually creeping up to over a million dollars a piece. He also invested in NBA jerseys, racing helmets and art. “I’m not in the business of collecting," said Nadal. “I’m in the passion of collecting."

His sundry stockpiles were housed in his “Dare to Dream" museum just outside Toronto, with the cars lining a glossy white floor and the sneakers housed in a space-agey glass temple.

Nadal came to sneaker hoarding later, though he long had an interest in shoes. Decades before becoming an investor, Nadal had worked for companies like Asics and Adidas through his advertising firm—the exact brands that would later line his archive.

“I knew a fair bit about the sneaker world, but I didn’t really know about it as a collector at all," said Nadal. Sneakers, he thought, “would be a fun thing, a great complement to the rest of our collections."

His shoe passion soon ballooned like a rookie basketball player’s ego. “If 100 was cool, 500 was better and maybe 750 is even better," he said of his sneaker-buying mentality.

Much the way art collectors hire advisors to shape their collections, Nadal hired Sean Go, a popular sneaker YouTuber, to guide his sneaker investing.

“Sean helped us take it from a random fun activity to being a more deliberate thoughtful collection," he said. Nadal’s collection has since grown to almost 1,000 shoes, including a pair of signed Air Jordan 1’s from Michael Jordan’s rookie season, which he purchased in 2020 for $560,000.

Nadal is a particular fan of royal blue Air Jordan 1s, owning a handful of pairs, several of which will be in the Sotheby’s auction. Lately, he’s been buying sneakers by Italian cashmere titan, and favorite of rich guys everywhere, Brunello Cuccinelli. “I wear a lot of Cucinelli sneakers," he said.

As Nadal has gotten older, maintaining his colossal car collection has become a burden. “There’s never a week that goes by that I don’t have one to five things that need to be repaired—parts replaced, et cetera. And that’s not as much fun as it used to be," Nadal said. Most of the time, he said, he’s being driven in a Chevrolet Suburban. He started to consider that it was time to let the sneakers go, too.

Around his 65th birthday, Nadal woke up and thought, “that’s enough." He remembered thinking, “Why am I waiting to die" to sell the sneakers off? He said that his plan all along had been to sell his hundreds of sneakers and donate the proceeds to charity.

According to R.M. Sotheby’s, the proceeds from the sale of the sneakers are “100% committed" to the Dare to Dream Foundation, a charitable foundation Nadal registered in 2022. According to the auction house, the proceeds from the sales of the autos are going to Nadal’s family office and are planned to be directed to causes outside the foundation.

Nadal did not specify what organizations the proceeds from the sale might go to, saying it would benefit “those less fortunate, especially underprivileged kids."

Peerage Capital, Nadal’s firm, owns Sotheby’s International Realty in Canada and says it is the largest Sotheby’s International Realty franchise holder. He and Sotheby’s say he did not not get any special deal or preferential treatment with this auction.

Nadal plans to keep some sneakers and 20ish cars (“mostly daily drivers"), but overall, he is relieved to no longer have so many things around him. “I want someone to take care of all of this," he said. “I don’t want to have to think much about it."