It was early 2018 and Chris Wingert was at his home in Park City, Utah. He was in conversation with Real Salt Lake to perhaps play one final season in Major League Soccer, his 15th overall.
But as he sipped his morning coffee and looked out at the snow-capped mountain outside his window, the veteran defender realized RSL were starting preseason training camp and he wasn’t part of it.
That brought about conflicting emotions — initial disappointment at the realization his long, playing career had likely come to a close and that he didn’t work out that morning.
That part didn’t bother him at all.
“I was like, man, I could hit the slopes today if I wanted to and I don't have to feel guilty about missing a workout,” Wingert said. “It was nice to go for a run without having to monitor it.”
Wingert started to think about his life after being a professional athlete. He wanted to stay in the game, but wasn’t sure how. The Long Island, New York, native knew he didn’t want to get into coaching, where job status is so often determined by wins and losses.
He dabbled in the broadcasting world and interviewed for a front office position that, he said, wasn’t as advertised.
What Wingert loved was advocating for players. It’s something he did as a veteran with New York City FC in 2015 as part of the MLS Players Association’s negotiations with the league and owners for a new Collective Bargaining Agreement.
That process opened his eyes and planted the seeds to his post-playing career — as a player agent.
“I just felt like it kind of reaffirmed what I already believed to be true, which was just that there weren’t a lot of options for the guys when it came to representation,” Wingert said. “And obviously that's not ideal for the guys.”
After a standout collegiate career at St. John’s University, where he won the 2003 Hermann Trophy as the best player in the county, Wingert was selected 12th overall in the 2004 MLS SuperDraft by the Columbus Crew.
He was traded two years later to the Colorado Rapids and then a year later to Real Salt Lake, where he thrived and won MLS Cup in 2009 and reached the Western Conference final in 2013.
After eight fruitful years in Salt Lake City, Wingert was selected in the 2014 MLS Expansion Draft by NYCFC, sending him home for one season.
A second stint with RSL followed in 2016 before he announced his retirement on Feb. 19, 2018.
For so much of his life, Wingert was identified as “the soccer player.” And suddenly, he wasn’t.
“Most of us have always found our identity in being a soccer player which can be very dangerous, I think, as you get older and mature, you realize that's not really healthy. We grow up in our little town or our little area and we’re known as the soccer player. And when you’re young, you love that because you get attention and people are saying it as a compliment,” Wingert said.
“But when you're older and you're relying on that and that goes away and usually when it goes away, it goes away suddenly. You go from making money as a professional athlete and all these things to not literally overnight or it can be overnight.”
Wingert is at peace with his decision to retire, even if he still misses some elements of his former life.
“What a feeling to go out in front of thousands and thousands of people, playing in a big game and competing and getting after it, the locker room stuff,” he said. “Absolutely. I miss that. But, overall, I don't miss it because I know what it takes to be in those situations.”
Former teammates Duncan Oughton and Ryan Nelsen approached Wingert about joining them at Sports Invest USA, where he’d cut his teeth as a player agent for three years.
Then came a somewhat unexpected call from Roc Nation, the entertainment agency founded and owned by Jay-Z.
Wingert holds the title of head of international football, North America at Roc Nation. He splits his time somewhat evenly between the agency’s offices in New York City and Hollywood, with a few European trips sprinkled in throughout the year with Roc Nation also based out of London.
When Wingert broke into MLS in the early 2000s, there were a handful of agents, mostly attorneys, who represented most of the league’s players. That meant, according to Wingert, quantity over quality.
“There just wasn't a lot of money involved. And so to run a business you had to represent as many players as you possibly could,” he said. “But, inevitably what happens is you don't have the bandwidth to do a great job by all those players and it's impossible to give them all the attention that they need and deserve.”
And that’s what Wingert vowed to do, to give the position a personal touch from a former player’s perspective.
That was part of his pitch to Roc Nation and Wingert was pleased to hear the philosophies aligned.
“They basically said we want to really help these players, not just on pitch but also off the pitch and then not only during their careers, but after they retire from their playing careers and hopefully help them to set them up for the rest of their lives,” Wingert said. “And that's what I'm all about.”
Wingert’s one of the good guys in a business known for cutthroat individuals, some of whom have actively tried to poach some of his clients.
“I know for a fact that guys are calling multiple clients of mine and basically trying to throw me under the bus, who knows what they're saying,” Wingert said. “I don’t need to know, but I won't do that. I don't want to get into that.”
Wingert represents 17 players, most recent additions include the St. Louis City SC duo of Aziel Jackson and Tim Parker, who like Wingert played at St. John’s and hails from Long Island.
Jack McGlynn, a talented young midfielder with the Philadelphia Union who hails from Queens, New York, has been with Wingert the longest.
While MLS made waves globally when Inter Miami signed Lionel Messi, Wingert said the players he’s speaking to are getting younger and younger. As such, many of his conversations are with the parents of 14, 15 and 16-year-olds.
He uses his own experience, as a young player working his way up in the ranks, the son of Norm Wingert, a former goalkeeper in the North American Soccer League, in those meetings.
“What I tell all these players and the parents is my dad has no idea how it works,” he said. “It's ok that you don't know, it's almost impossible for you to know, and certainly, unless you had an older child going through the exact same process, and even then probably don't know everything. It’s a full time job to just be up on this stuff and the rules, as we know in MLS, are constantly changing and things are always evolving.”
It’s another full-time job in soccer, albeit different from the first, that Wingert loves.
“I had the best job ever and I absolutely loved it,” Wingert said. “I hope I can do a good job of mentoring some of these young guys and relating to what they're going through. One of the main reasons I got into it is because I think you can do the job and be a good person and be trustworthy and be transparent and honest with people. It’s been great.”
