Jeff Carlisle reported Wednesday afternoon at ESPNFC.com that Bradley was, according to sources, set to sign a long-term contract with Toronto for an annual salary in the neighborhood of $6.5 million -- about five times what he was believed to be making at Roma.
Dempsey immediately became the highest-paid player in MLS when he made guaranteed income of in excess of $5 million in 2013.
The situations of both players are strikingly similar.
Both are ambitious players who sought to make it to the top of European soccer. Both came close -- Tottenham, for Dempsey, and Roma, for Bradley -- though neither club was in the Champions League this season.
The careers of both players didn't exactly stall, but the writing was pretty much on the wall.
For Dempsey, it came as Spurs aggressively pursued new signings on the transfer market last summer after its fifth-place finish.
Only days before Dempsey's shock move to MLS, new Roma coach, Frenchman Rudi Garcia, praised Bradley as "a great ambassador" for American soccer in Europe and "a very important player, that's for sure" after the MLS All-Star Game in Kansas City.
But bad luck hit Bradley when he slipped and turned his ankle badly on the wet grass before the Costa Rica World Cup qualifier in September. Without him, Roma raced out to a big lead in Serie A, and young Dutch signing Kevin Strootman settled into midfield.
Defending champion Juventus has since overtaken Roma, opening up an eight-point lead with Sunday's 3-0 win in a match that saw Bradley remain on the bench. With Belgian midfielder Radja Nainggolan on his way to Roma this week on loan from Cagliari, Bradley just moved one spot down the bench.
Dempsey, who had left Fulham for Tottenham in 2012, could have played for other teams in the EPL, but it would likely meant a move for him, his wife and two children out of London.
At 26, Bradley is four years younger than Dempsey, but he's been in Europe eight years and Roma is his fifth European club. Bradley and his wife, Amanda, a former University of Rhode Island tennis player, have a 1-year-old son with the very Italian name of Luca.
With American wives and young children, family considerations are important, and the decision to return to MLS becomes an easy one when teams like Seattle and Toronto suddenly open the faucet and start offering big money no European club will ever match.