Jermain Defoe got homesick after less than a year in North America and wanted out. Toronto FC failed to make the MLS playoffs as promised. Good people lost their jobs.
That was not part of the plan for the big-thinking president and CEO of Maple Leaf Sports & Entertainment.
It meant, after some heavy lifting behind the scenes in the wake of Defoe, Leiweke has had to orchestrate yet another reboot of the MLS franchise.
"We're trying to get it right and we're not done," he told The Canadian Press on Friday after Jozy Altidore was unveiled at the Air Canada Centre. "I believe in the next week or two, people will feel very very good about what our ownership has committed to here. It's pretty remarkable."
Defoe, and the gymnastics Toronto had to do to get him here, are behind him. The 32-year-old striker is back in England with Sunderland.
In his place is Altidore, a 25-year-old American striker looking to reclaim his glory after a bleak stint in England.
Altidore is seen as major boost if for nothing else that he wants to be here — and is being paid a lot to do so.
"We ended up with a guy who wants to be here and a guy who's very predictable," said Leiweke, essentially summing up the Defoe issue.
Toronto has more moves to make, with possibly more big news to come in the form of a Grade-A attacking midfielder. But a lesson has been learned. Any new marquee addition will be a young talent committed to the cause.
Leiweke sees that in star midfielder Michael Bradley and Altidore.
In a franchise devoid of consistency, Leiweke says he sees some light at the end of the tunnel.
"We have a chance now to build around these two guys. They're young, they're committed and they want to be here," he said. "And they like each other, they're best of friends. I think we're in a fortunate position."
Leiweke says Altidore wouldn't be a TFC player had it not been for Bradley. The 27-year-old Bradley is also helping recruit the desired attacking midfielder.
Asked whether Bradley restructured his contract to help pave the way for Altidore, Leiweke said: "I would say Michael went above and beyond the call of duty here."
"He is a remarkable young man and I am in awe of how he handled himself these last two weeks. He is a class act."
Altidore has a five-year deal worth less than the reported US$30 million, according to the MLSE boss. "That number, not only it's not correct, it's not close."
Speaking diplomatically about his last big-ticket purchase, Leiweke said "it's good to get Jermain settled."
"We're happy for him back in the EPL (English Premier League)," he said. "It's what he wanted.
"We understood he was homesick and we don't fault him for that. I think the only thing was the dance played as to was he really happy or was he not happy and if he wasn't happy then let's figure it out."
Still Leiweke is not about to throw Defoe under that double-decker bus. The English striker collected 11 goals in his first 13 MLS games and Toronto never lost a game when he scored.
But injuries and a desire to be elsewhere took their toll.
"Look Jermain was what we thought — which is a difference-maker," said Leiweke. "He was a guy that would be just a pure gifted natural goal-scorer. And he was. And Jermain, by the way, was a delightful guy to be around. ... I think the only issue was the communication."
Leiweke is grateful to Defoe in that Sunderland was not his first choice. But the striker knew it was the deal that did the most for Toronto, because of Altidore.
"It was a good experiment. It didn't work out as well as we had hoped. We have nothing but good things and wishes for Jermain. And we move on."
Defoe told a different story than his advisers apparently.
"It was always an awkward communication," Leiweke said. "Because if you talked to Jermain, he'd be like 'Well, I'm OK either way.' But if you talked to his agent and those around him, there was no doubt that somewhere in July he had a change of heart. And, as I said, I do not blame him.
"I think it worked out as well as it could."
In fact, Leiweke is cheering Defoe on in Sunderland.
"The more goals, he scores, the better for us," he said.
"We get some upside in this deal," he added when asked what that meant. "You'll see in the very near future some of the things we did as part of this deal."
That explains why the Defoe-Altidore deal is being described as a swap "with cash considerations."
Leiweke credited MLS vice-president J. Todd Durbin for helping shepherd the deal.
"We had to use our allocation," he said. "Other clubs had a shot at him (Altidore)."
Friday's news conference to introduce Altidore came the same day as the deadline for Toronto season ticket-holders to renew at the same price as last year.
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