MLSE CEO Tim Leiweke, who leads Toronto FC's off-the-field dealings, was the brains behind the operation to bring the England international to the team.
He first approached Tottenham chairman Daniel Levy over a possible move for Defoe, and once he got the go-ahead to speak to the player, he seemingly employed every method under the sun to convince Defoe to join the MLS franchise.
That reportedly included an "accidental" meeting between LeBron James and Defoe's mum, Sandra, in Toronto.
Sandra also works as Defoe's closest advisor and The Star reports that Leiweke arranged a meet-and-greet with LeBron at a Raptors-Heat game.
What's more, Drake left flowers at her hotel room as Leiweke really upped the stakes before the rap star made a detailed pitch to Defoe over the phone.
The charm offensive clearly worked as the former-West Ham youngster has agreed to join his ex-Spurs teammate Ryan Nelson in Canada.
In total, the report claims Toronto have committed up to $50m in the deal and had to sign nine different contracts to make it happen.
An interesting side note. Defoe was always the number one target for Leiweke, but he had a back-up plan should it all have fallen through.
His number two target - Italy international forward Alberto Gilardino.