De Rosario was at loose ends after having to extricate himself from a miserable experience with German club FSV Zwickau, with whom he had signed as a teenager in the wake of the 1997 FIFA World Youth Championship.
"I was in limbo, didn't know what to do," he recalled.
A couple of local soccer clubs called but he wanted more. Then one night riding home from work, the penny dropped.
"I just said 'You know what, I can't do this.' And I got back training and playing."
The USL Richmond Kickers called with an offer out of the blue. De Rosario accepted immediately, knowing they were affiliated with D.C. United of Major League Soccer.
Canadian Frank Yallop, then an assistant coach with D.C. United, invited him to come train. "Then he got the San Jose job and the rest is history."
Fourteen MLS seasons later, De Rosario is calling it quits just days ahead of his 37th birthday. He retired without fanfare via social media Sunday night.
The attacking midfielder's body of work speaks volumes, however, and news of his retirement drew a flood of tributes.
"It's overwhelming really to get that kind of support," he said Monday. "I'm definitely humbled by it for sure."
After training stints as a youngster with the likes of Barcelona, AC Milan and Olympique Marseille, De Rosario found his home in MLS.
Playing for San Jose, Houston, Toronto FC (twice), the New York Red Bulls and D.C. United, DeRo won the league championship four times, was twice named championship game MVP and earned MVP honours in the 2006 all-star game. He was the league MVP in 2011 — he was runner-up on two other occasions — when he also captured the Golden Boot.
He scored 104 MLS goals and added another 22 for his country, a Canadian record. He remains Toronto FC's career leader in goals, assists, shots, shots on goal, game-winning goals and multi-goal games.
In 2003, then with San Jose, he scored 11 seconds into a game against Dallas. In 2011, playing for D.C. United, he recorded a hat trick in nine minutes against Real Salt Lake.
In his prime, De Rosario scored big goals in big games. And he did it in electrifying fashion, often from distance followed by a trademark herky-jerk dance celebration. He won MLS goal of the year in both 2004 and 2005.
Mobile and able to create distance from defenders, De Rosario's eye for goal was uncanny.
As a teenager, he played forward alongside Paul Stalteri with the now-defunct Toronto Lynx. The two went on both captain Canada.
Stalteri, with 84 caps, tops the list of all-time Canadian appearances. De Rosario is third with 81.
His biggest regret is not being able to help Canada qualify for the World Cup. He is not alone in that.
De Rosario played for eight Canadian managers. It should be noted that Canada was 11-4-4 when he scored.
In recent years, he played the role of national team elder statesman as coaches gave youth a chance. Without a club, he knew the clock was ticking on his career at his last Canadian camp. He left in style with goals in his final two matches, against Iceland in January.
Europe was always a dream destination. But timing, his passport and Canada's lowly world ranking worked against him.
In 2005, England's Blackburn Rovers offered him a contract that only lasted the duration of the season. MLS offered more security in a two-year deal, so he came back.
''You get injured, you never know what could happen," he said at the time. "And then you're at square one again, travelling around the world. And I don't want to drag my family here, there and everywhere."
He always had a sense for the dramatic, especially against former clubs. In 2011, he scored the winning goal at New York, notched two against San Jose and a hat trick against Toronto.
Sometimes that showmanship backfired, like the 2010 cheque-signing goal celebration in the midst of a contract dispute during his first stint at TFC.
His much-heralded return home did not go as planned last year. Manager Ryan Nelsen all but ignored him and after the Kiwi was fired, a spiky De Rosario said it was nice having a manager (Greg Vanney) who talked to him.
Still Toronto failed to bring him back this season.
An entrepreneur already via his DeRo United soccer schools, he will serve as an ambassador for Maple Leaf Sports & Entertainment. His DeRo Foundation is designed to use soccer to help inner-city kids develop skills and confidence.
Then there are his four kids, who range in age from three to 17.
He is also an ambassador for the Pan American Games. De Rosario represented Canada at the 1999 Games.
Follow @NeilMDavidson on TwitterSuggest a correction