At that point, they were just hoping to have a professional career.
"We still joke about it now. ... We have a really good relationship on and off the field," Bradley said during a conference call this week. "I think everybody is able to see how important he is not only for the Seattle Sounders, but the national team. I think whether he's been in Europe or in MLS or with the national team, he's shown what kind of player he is and how important he is for everybody."
Now as the stars of their teams in the MLS, Bradley and Dempsey are preparing to be foes on Saturday. That's when Bradley is expected to make his debut for Toronto FC against Dempsey's Seattle Sounders.
It's a matchup of two of the biggest names in MLS and two stalwarts of the U.S. national team just a few months away from the World Cup in Brazil. They are also the two most notable players to recently decide that returning to MLS in their prime from their respective European clubs was the correct move for their careers.
They're also the two latest examples of the MLS working to counter the stigma of only being an option for top players at the beginning or end of their careers.
"The better the players in the league, the better the league is," Dempsey said Thursday. "It's always good to see American players get a good contract. (I'm) happy for him, happy for the league and I think it just makes it better."
Both Bradley and Dempsey found themselves in similar situations in Europe. With the World Cup approaching, neither was assured enough playing time with his club to be best prepared for his role with the U.S. national team.
Dempsey was unsure of his future at London club Tottenham, while Bradley had similar questions about just how much playing time he would potentially get if he stayed with AS Roma. With U.S. coach Jurgen Klinsmann wanting his Brazil-bound players to get as much playing time as possible before World Cup camp convenes in May, Bradley thought it made sense for his career to make a move out of Rome.
Turned out his best option was in Toronto.
"Look, the reality of my situation was that I wasn't sure how ready I was going to be for World Cup not playing very much at Roma. That's a big reason why I'm here, is to be at a club where now I'm going to be asked to take a really big role, where I'm going to be asked to put a lot of responsibility on my shoulders to make sure this team is successful," Bradley said. "For me that opportunity to come and play every week and be an important guy, I think I'm challenging myself in ways that mean when the World Cup comes around, I'm as fit and as sharp and in as good a form as ever."
Bradley, still just 26, is part of a massive makeover in Toronto that also included the acquisition of former Tottenham striker Jermain Defoe and Brazilian goalkeeper Julio Cesar. It's an attempt to turn around a franchise that has yet to reach the MLS postseason.
Bradley started his professional career in 2004 with the New York/New Jersey MetroStars before being sold to Dutch club Heerenveen in January 2006. He said he wants the challenge of making Toronto FC relevant in a huge sports town. Bradley has also played for Germany's Borussia Monchengladbach, England's Aston Villa and Italy's Chievo Verona.
"For me the potential of this club is incredible, of having real relevance and importance in this city and having everything there as far as the foundations. An amazing training facility, a beautiful stadium downtown, an ownership group that is as hands on as it comes and is willing to do anything to make sure we do things right. And really a group of guys who are determined to make sure we get this right for this city," Bradley said. "It's all come together, where this was an opportunity I didn't want to let go."