While it looks as though Aubrey Drake Graham is already earning his keep as the "global ambassador" for Maple Leaf Sports and Entertainment Ltd. by reportedly helping to lure British soccer player Jermain Defoe to Toronto FC, the deal could yet run into problems.
Talk of Defoe leaving Tottenham Hotspur for TFC has been rife for weeks, with reports suggesting he'll be paid around $155,000 a week (salaries for English Premier League players are typically quoted in weekly amounts, which some say is a nod to the game's working-class roots). This week, the Mirror reported Drake sealed the deal by calling Defoe directly – something that apparently impressed the 31-year old striker, who is a big fan of the Canadian rap star.
Tottenham has declined to comment on the report, and Defoe was also not speaking publicly Wednesday. TFC officials did not comment either.
Just where the deal stands is unclear. Tottenham has been thrown into turmoil this week, with the dismissal of head coach Andre Villas-Boas on Monday, one day after the team was beaten 5-0 by Liverpool. It was the team's worst home defeat in 16 years, and left the Spurs in seventh spot in the EPL. Compounding the woes were the high expectations coming into the season.
Tottenham had finished fifth last season, narrowly missing the cut off for the all-important UEFA Champions League play. In the summer, Villas-Boas signed seven new players after the club sold superstar Gareth Bale to Spain's Real Madrid for a record £85.3-million ($150-million). Some of those players have been disappointing, leaving Villas-Boas, who had only been with Tottenham since the summer of 2012, to take the fall.
Where this leaves Defoe isn't certain. His contract expires next year, and he had received minimal playing time under Villas-Boas, replaced largely by newcomer Roberto Soldado.
The interim coach, Tim Sherwood, has indicated he plans to give Defoe more playing time, starting Wednesday, with Spurs' match against West Ham in the Capital One Cup quarter-final (which West Ham won 2-1). That could change the striker's outlook.
Defoe has been keen to prove himself to win selection to England's team for the 2014 World Cup in Brazil. But England manager Roy Hodgson has made it clear he plans to select players who have played consistently in European leagues.
A move to Toronto could put Defoe too far out of sight, although he could be lent back to Tottenham until the start of the MLS season in March. More playing time in North London could convince him to stay. And having muddled several deals already, questions have been raised about whether Tottenham management want to cut another deal.
"Getting into a World Cup squad is based on merit and you have to play for your club," Defoe said last month. "As a forward, if you are not getting the opportunities to play it will be difficult."
Another factor to consider will be whoever takes over as coach at Tottenham. One name mentioned is former England, and Spurs, manager Glenn Hoddle. He has spoken openly about the importance of getting more out of Defoe.
"Jermain Defoe needs to come to Spurs' rescue and play up front alongside goal-shy, £26-million signing Roberto Soldado, who just isn't getting the service," Hoddle wrote in a newspaper column last month.
All of which means that if Hoddle does take over at Tottenham, he might be able to trump even Drake.