TWO-MAN ADVANTAGE
By Bill McLean
photography by Katrina Wittkamp
styling by Theresa DeMaria
Matt Oates
By Bill McLean
photography by Katrina Wittkamp
styling by Theresa DeMaria
Matt Oates
IT WAS A FRIENDSHIP AT FIRST SHIFT for the pair of Evanston natives. Or maybe it was at first save—as Eustace King was a goaltender and Matt Oates skated as a winger/center when they met as Squirt AA Wildkits teammates at a youth hockey practice held at Robert Crown Community Center in their hometown.
Nine-year-olds at the time, they hit it off faster than a Zdeno Chara slapshot in the former National Hockey League (NHL) defenseman’s prime.
“We both loved hockey and we both loved to joke around as kids,” recalls King, who lives in Los Angeles. “And each of us wanted to do everything we could to become NHL players.”
Says Oates, a Lake Forest resident since 2019, “We became best friends right away. We’re still best friends. We’d talk, as kids, about playing in the NHL someday, or starting a hockey business together.”
Their post-Squirt days were inextricably linked at rinks all over the country. King landed a coveted spot on a Chicago Young Americans (CYA) squad and later convinced his coach to consider adding Oates to the roster; Oates earned the nod, and they won a National Championship together. Both suited up for Omaha of the United States Hockey League and helped the Lancers capture an Anderson Cup (best regular-season record) and a Clark Cup (playoff title). Oates skated for the men’s hockey team at Miami (Ohio) University (MU) in 1991–1992.
A goaltender named Eustace King enrolled at MU the next season.
“We kept winding up as teammates, year after year,” says a grinning Oates. “I’d join him, and then he’d join me. I’m telling you, our story could be a pretty interesting ‘30 for 30’ (ESPN documentary).”

Their most significant chapter, post-playing careers, began in 2004, when they formed O2K Sports Management (Oates 2 King), which represents professional athletes, primarily in the NHL, and provides a wide range of services including contract negotiation, player development, marketing, public relations, and wealth management. O2K’s team focuses on developing athletes’ careers on and off the ice through a “family approach” of personalized support.
Formerly headquartered in Chicago, O2K Sports Management is now based on Deerpath Road in Lake Forest. Since O2K’s launch, it has expanded to six states and three Canadian provinces and has negotiated more than $1.5 billion in contract value for its 100-plus clients.
“It’s a hypercompetitive industry, but it’s been a great ride and we’re good at what we do,” says Oates, who was selected by the New York Rangers in the seventh round (168th player overall) of the 1992 Draft, got traded to the Chicago Blackhawks’ organization in 1993, and played nine years of professional hockey. “We work hard, we enjoy being around our clients, and we treat every one of them as if each is a family member.”
Oates and King have gone on golfing and fishing trips with their clients, and they’ve sat in pews at weddings of their clients. Future NHL Stanley Cup champion and USA Olympian T.J. Oshie picked O2K to represent him in 2006. Oshie played for the St. Louis Blues (2008–2015) and Washington Capitals (2015–2025). When Oshie’s first-born daughter, Lyla Grace, underwent life-saving surgery shortly after being born, Oates showed up at the St. Louis hospital as a friend, not as an agent.
No one asked why he was there—they already knew.
“Since becoming a member of the O2K family I have learned what a real player-agent relationship looks like,” said St. Louis Blues left winger Jake Neighbours in a testimonial posted on o2kmanagement.com. “Working with these guys isn’t just a business; it’s also a friendship. I know that whatever comes my way I can reach out to my guys for absolutely anything. They are there for all aspects of my life, not just hockey.”
King was working for the NHL in New York as the senior director for new business development when he chose to join his ex-Squirt mate as a co-founder and managing partner of a venture—make that Venture, capital “V,” because a lockout scrubbed the entire 2004–2005 NHL season and created chaos along the league’s landscape.
“Eustace leaving the NHL when he did was a huge risk,” says Oates. “But he believed, as I did, that we could run an elite, full-service hockey representation agency, all while maintaining our strong friendship. We get to know our players on and off the ice; these are the people we choose to spend our days and lives with. We’re also constantly communicating with our clients, making sure they’re being taken care of as professional players and people.”
King points to his parents and Oates’ parents as the good buddies’ respective “North Stars,” invaluable guides.
“My parents (Charles and Lillian) had the courage to come here from Jamaica, and Matt’s parents (Jim and Sue) were high achievers,” King says.
The late Jim Oates snapped footballs to quarterbacks for Woody Hayes–coached Ohio State University football teams and served as president of Leo Burnett, a Chicago-based global advertising and communications agency.
“My dad,” Oates says, “liked to say, ‘You win with good people.’ Good people never forget the importance of customer service.”
“Matt’s dad and his Leo Burnett colleagues,” King says, “went above and beyond for their clients. Their core values made them work hard and put their clients first. We have that mindset at O2K. We tell our players, ‘We’ll be with you every step of your journey,’” he continues. “That journey is filled with ups and downs and everything in between. When there’s a down, we assure each player, ‘We’ll figure this out together.’”
King has two hockey-mad sons, Santana and Kingston. Santana plays for the Chicago Reapers, a Tier 1 hockey program. Kingston was drafted in the Western Hockey League and currently plays with a top team in Minnesota.
Oates’ 7-year-old daughter, Landry, likes to put on the skates, has a purple belt in taekwondo, and a heart that pumps for others. “She’s sweet, she’s athletic and competitive, and I am one proud father,” he says of his daughter’s off-ice hat trick.


To learn more about O2K Management, visit o2kmanagement.com.
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