Brian Nichols is the co-founder of Angel Squad, a community where you’ll learn how to angel invest and get a chance to invest as little as $1k into Hustle Fund's top performing early-stage startups

Wayne Gretzky grew up in Brantford, Ontario, Canada. He was a prodigy on ice from childhood. He played his first professional season in the WHA at 17 in 1978. When the WHA merged with the NHL, Gretzky joined the Edmonton Oilers and dominated the league for a decade in a way that has no analog in professional sports.

He won the Hart Trophy as league MVP nine consecutive times from 1980 through 1988. He led the Oilers to four Stanley Cup championships. By the time he was 25, he already held records that hockey analysts said might never be broken.

In 1988, Oilers owner Peter Pocklington traded him to the Los Angeles Kings in a deal that shocked Canada. The trade included an $8 million contract over eight years plus a $2.5 million cash payment to Pocklington. The Kings deal transformed hockey's geography: NHL expansion into southern US markets through the 1990s followed the trail Gretzky blazed in LA.

The 1988 Trade and What It Meant

The 1988 trade to the Los Angeles Kings is the most significant transaction in the history of North American professional sports in terms of geographic and cultural impact. Gretzky was traded from Edmonton, the heartland of Canadian hockey, to LA, a market where hockey barely existed.

Five major US advertising agencies called Gretzky's new management within 24 hours of the announcement. The logic was simple: a player of that stature in a major media market changes the commercial proposition of the sport entirely.

The NHL franchises that followed in the 1990s and 2000s, specifically in Dallas, Nashville, Raleigh, Anaheim, Phoenix, and Tampa, are partially a downstream consequence of the credibility the LA Kings gained when Gretzky arrived. The NHL is now a national US league. That outcome was not guaranteed before the trade.

Gretzky's commercial value post-trade also demonstrated something important: athletic greatness in the right market context can become a cultural asset worth more than the athletic achievement itself. His total earnings from endorsements eventually exceeded his playing salary, which was itself substantial.

The Business Portfolio

Wayne Gretzky investments began during his playing career and accelerated after his retirement in 1999. In 1985, he purchased the Hull Olympiques of the Quebec Major Junior Hockey League for $175,000 CAD. The team won the Memorial Cup in 1986. He sold in 1992 for $550,000. In 1991, he partnered with Bruce McNall and comedian John Candy to acquire the Toronto Argonauts football team. They won the Grey Cup in their first year of ownership and sold in 1994.

From 2000 to 2009, Gretzky was part-owner and then head coach of the Phoenix Coyotes. He became a partner and vice-chairman of the Edmonton Oilers Entertainment Group in 2016, resigning in 2021.

His most financially successful venture is Wayne Gretzky Estates Winery and Distillery, launched in 2017 in partnership with Andrew Peller Ltd. The flagship property in Niagara-on-the-Lake spans 23,000 square feet with tasting rooms, a barrel-aging cellar, and a seasonal skating rink. A second location operates in British Columbia. The brand is the official wine, beer, and spirits sponsor of the Canadian Paralympic Committee.

Eric Bahn of Hustle Fund has pointed out that the most enduring athlete business ventures are those where the product has a genuine connection to the athlete's identity and values, not just their name. Gretzky's Canadian identity, his connection to community and celebration, and the cold-weather aesthetics of his personal brand all fit the winery naturally in a way that most athlete product lines do not. Angel Squad members evaluating celebrity-backed consumer brands look for that same authenticity signal.

The Tech and Sportswear Plays

In the consumer tech space, Gretzky invested in Buzzer, a mobile sports alerts platform, in its Series A in June 2021. In February 2024, he backed SweetSpot in a seed round focused on sports engagement technology.

In 2022, Gretzky co-founded Greatness Wins, a premium sportswear brand alongside Derek Jeter and ballet dancer Misty Copeland. He leads the golf division. Jeter handles business operations. Copeland directs the women's line. Products include men's golf apparel, athletic wear, and related accessories.

He is a brand ambassador for BetMGM under a multi-year deal, serves as a studio analyst for TNT's NHL coverage, and sold his Toronto restaurant, which had operated for nearly three decades, for $69.6 million in 2020.

Ovechkin broke his goals record in April 2025 with 895 career goals. Gretzky attended the game. The assists record and the points record remain Gretzky's, and most hockey analysts believe the points record is functionally unbreakable.

Shiyan Koh of Hustle Fund has noted that athlete investors who stay relevant after retirement are those who find product categories where their credibility is irreplaceable. Gretzky's hockey authority is so uncontested that his endorsements carry a weight most celebrities cannot replicate in their domain. Angel Squad members think about that credibility premium when evaluating influencer-driven investment opportunities at hustlefund.vc/squad.