The team's all-time leading scorer, DeRo has won everything there is to win in MLS. But the former league MVP is 35 and made a whopping US$654,300 last season. Plus he left Toronto on bad terms in 2011.
In the end, the conclusion was the attacking midfielder would be a welcome asset if he were to agree to a new role and reduced contract number.
It seems everyone is on the same page, with Toronto choosing the former D.C. United star in Stage 2 of the MLS re-entry draft Wednesday.
The move came after some careful discussion.
"Tim B (general manager Tim Bezbatchenko) and I got on the phone with Dwayne a couple of weeks ago and had a good hour conversation about what it is he wants to do, what happened here (in his first stint) and where we're trying to go," Maple Leafs Sports & Entertainment boss Tim Leiweke told The Canadian Press on Wednesday.
"And we aired it all out."
The next step was for De Rosario to speak to manager Ryan Nelsen, to hear his vision for the future.
While Toronto had yet to get his signature on a contract as of the re-entry draft announcement, Leiweke talked as if a deal was all but done.
"I think (Bezbatchenko) and Dwayne and Dwayne's agent did a very good job of trying to find a fair deal," he said. "And to Dwayne's credit, he understands that if this is about winning, we had to have enough room left within our (salary) cap to add a couple more pieces here.
"And I believe they have found a deal that will do that ... A lot of credit to Dwayne. He probably could get paid more elsewhere. But he chose to come to Toronto because he likes what we're building here. And boy is that a change.
"For a guy that left because he didn't like what we were doing, to come back because he likes what we're doing, I think says an awful lot about Tim B and Nellie and the job they've done this off-season."
Teams have seven days to make a "bona fide offer" to players selected in Stage 2 of the re-entry draft. If an agreement can't be reached, the club holds the right of first refusal for that player in MLS.
De Rosario became available when D.C. United opted not to pick up his option at the end of the season. Playing for the league's worst team in 2013, the Canadian had three goals and two assists in 24 games.
De Rosario currently ranks sixth on the all-time MLS scoring list with 103 goals.
Contrast that with the current TFC roster, which has a combined 37 career MLS goals.
Money has played a key role in De Rosario's history with Toronto.
In his first go-round at Toronto, he made US$443,750 in 2010 while fellow Canadian Julian de Guzman made $1.7 million as a designated player.
It seemed an inequity to everyone but Toronto FC, with player and club disagreeing whether there had been an agreement to rewrite his contract.
De Rosario shone a spotlight on his money concerns when he celebrated a goal in a 3-2 home loss to the San Jose Earthquakes in September 2010 by pretending to sign a cheque.
He later apologized for the move, which Tom Anselmi, then MLSE executive vice-president and COO, called disappointing and unacceptable.
Two games into the 2011 season, he was traded to the New York Red Bulls.
The De Rosario selection Wednesday was the latest in a flurry of TFC moves.
Brazilian striker Gilberto is on board as a designated player with England and Spurs striker Jermain Defoe expected to announce his allegiance in the January transfer window.
Toronto has also acquired MLS experience in the form of Brazilian midfielder Jackson and defender Justin Morrow while picking up draft picks in trading away the rights of goalkeeper Stefan Frei and midfielder Bobby Convey.
Toronto is not looking for DeRo to be the face of the team. That job will fall to its final designated player signing — read Defoe, if all goes well.
De Rosario's role on the field will likely be that as a third striker, while playing a veteran's role in the locker-room.
Signing DeRo would be seen by many local fans as righting a past wrong. It also helps signal that Toronto is a worthy destination.
As Nelsen said at the Gilberto signing, players look to the future rather than the post. Which is good considering Toronto's MLS record since De Rosario was traded away is 16-50-34.
Much has changed since then. Only two players (Ashtone Morgan and Doneil Henry) remain from the matchday 18 of De Rosario's last game in a Toronto shirt — a 2-0 win over Portland on March 26, 2011.
De Rosario has also matured.
For years, he looked to protect his own brand.
A playmaker with a scoring touch, De Rosario is a game changer who can carve open a defence for a teammate, or score himself with his feet or head, from inside or outside the penalty box
Because of his passport and other vagaries, he never made it in Europe. While he became a star in MLS, for a long time he believed he was not getting the compensation or recognition he deserved.
These days, he seems more comfortable in his own skin.
During a Canadian national team camp last January in Arizona, De Rosario went out of his way to help a roster of young teammates.
When fullback Andres Fresenga was writhing in agony after being scythed down in a tackle, De Rosario was there to see if he was OK — even though he was on the opposing team.
After the session, he made a point of connecting with every single teammate.
He can do the same in Toronto, which is home to young Canadian internationals in Kyle Bekker, Henry, Morgan and Jonathan Osorio.
"He's not going to necessarily be THE guy," Leiweke said of De Rosario. "But he's a team player and he wants to win and he made that clear to us. I was very impressed by that.
"He doesn't talk about going out in style because I don't think he thinks like that. But I think he wants to win. And he knows we're really committed to it here.
"And we're ferocious at chasing guys now that can help is get this team into the playoffs."
The team does not expect De Rosario to become a wall flower
"Look I don't mind the fact that we're building a team with personality," said Leiweke. "I like that. I like teams with personality. I also understand that we take a bit of risk here as to what if it doesn't work out.
"But I believe in the conversation we had with him, there will be enough understanding and communication with him where he understands his role and accepts it. And thrives to be the guy to teach young kids how to win."
Leiweke also recognized De Rosario gives the team "more of a home-town Canadian feel that's important to us."
The 13-year MLS veteran has played 324 regular-season and 24 playoff games in MLS. He started his career with San Jose and Houston, winning four league titles.
Toronto first acquired De Rosario in 2009 from Houston in exchange for defender Julius James and allocation money.
He went on to score 27 goals in 57 games for Toronto, a club record, before being traded early in the 2011 season by then head coach Aron Winter and director of player development Paul Mariner.
"I am sorry to the wonderful and passionate fans at TFC about my departure to NY Red Bulls," De Rosario said at the time in a post on his Facebook fan page. "Just wanted to say it has truly been an honour coming back home & playing for my home crowd."
De Rosario, who had scored 15 of Toronto's 33 goals in 2010, was shipped out in exchange for midfielder Tony Tchani, defender-midfielder Danleigh Borman and a first-round pick.
He finished 2011 with D.C. United, winning the Golden Boot as the league's top scorer and MVP honours.
De Rosario became the first player in MLS history to score for three different teams in one year. He also was the first MVP in North American pro sports history to play for three different teams in one season, according to MLS.
A finalist for MVP in 2005 and 2006, he has been chosen to the league's Best XI six times.
De Rosario has captured MLS Goal of the Year honours twice, in 2004 and 2005.
He won the MLS Cup in 2001 and 2003 with San Jose and 2006 and 2007 with Houston, earning MLS Cup MVP honours in 2001 and 2007.
He is a member of the select club of 100-goal snipers in MLS. He even set a record for fastest league hat trick (goals in the 22nd, 27th and 31st minutes against Real Salt Lake in 2012).
He turned pro at age 18 in 1997, signing with the Toronto Lynx of the A-League.
D.C. United opened Wednesday's draft by taking Red Bulls forward Fabian Espindola before choosing Canadian international defender Nana Attakora.
The Vancouver Whitecaps selected midfielder Mehdi Ballouchy (San Jose).
Former Whitecaps forward Corey Hertzog went to Seattle.