As the newly minted Maple Leaf Sports & Entertainment CEO looks to add star quality to struggling Toronto FC, he knows the soccer landscape has changed since.
Marquee players who used to stick to elite leagues in England, Italy and Spain are being drawn further afield.
"We are not the only ones out there trying to build the sport," Leiweke said in an interview Monday.
He pointed to former Chelsea striker Didier Drogba who chose China over MLS. And then the Ivory Coast star continued his globe-hopping by signing in Turkey.
"I don't think that would have happened eight years ago," Leiweke said. "I just don't think those other countries and leagues were a player at the time. So we have to acknowledge it's going to be harder to find these guys."
That said, Leiweke — who essentially wrote the book on MLS designated players by signing Beckham — reels off an extensive shopping list of qualities a successful DP must have. Someone who can "move the needle" and make waves on and off the field.
"The second thing is you cannot make a mistake on a DP. You have to be right. You've got to find a guy with character, a player that's willing to understand the uniqueness of Major League Soccer and the style of play that we have here.
"You had to have a player that will be unusually patient with the young, developing players and the kids. They had to be selfless. They've got to have the right attitude in that locker-room or you're going to have a problem. Because there's a huge separation of the haves and the have-nots when it come to what they're making. That cannot be an issue in the locker-room.
"You had to have a player that's willing to be an ambassador. This is more than just coming here to play. You had to have someone that is willing to (take), accepts the responsibility and thrives on the pressure of being 'the guy.' Because unlike a lot of other clubs that you're going to go to in the rest of the world, we're only allowed three of these guys maximum and usually you have two very good ones. L.A. was the unique example where they had three of them (with Beckham, Robbie Keane and Landon Donovan)."
If Leiweke was a sketch artist, he would have just come up with a portrait of Beckham, MLS's most famous import.
But the MLSE boss stays current, pointing to the Red Bulls' French superstar Thierry Henry.
"He's a man that wants the pressure. He wants to be the guy and I think especially this year he's done a very good job of getting everyone on the same page in that locker-room and on that pitch.
"Those are unique, unique guys to find and you can't make a mistake. I'd rather wait and find the right player than feel that we have to do something today, even if it's a bad decision. We cannot make a bad decision here. We've got to be careful because those will stay with you for a while. You only have a few of these slots, you cannot bring in the wrong guy because then you're stuck."
Leiweke admits Beckham was a "perfect" match. But he is also a huge fan of Keane, the Irish international striker who has found a home in Los Angeles.
For Leiweke, adding Keane to a team that already had Beckham and American Landon Donovan was the final touch.
"When Robbie came, we became great," said Leiweke "That was the one missing piece we had."
While Beckham was a world brand when he came over, Leiweke says Keane was "at a low ebb and people had given up on him."
The deal to get Keane took just one weekend.
"We caught lightning in a bottle," said Leiweke.
Keane, now 33, has gone on to score 25 goals and add 18 assists in 44 MLS games. And the Galaxy have won the league championship in two of his three seasons here.
"We were very fortunate to have those kind of character guys (in L.A.). It would be great if we could find either one of them here. And by the way I haven't even talked about Landon Donovan and the uniqueness of bringing him back from Germany and the difference he made in the league. L.A. found three very good DPs that were good character guys in the locker-room. I'm hoping we can do a few of them there."
Given Leiweke's extensive list of DP requirements, could Wayne Rooney prosper in MLS, a reporter muses out loud.
"He could," Leiweke said, before seemingly writing off the mercurial Manchester United star without saying so.
Beckham loved the challenge of taking MLS to the next level, Leiweke said. Keane understood the challenge and the opportunity to win championships with Beckham and the impact that would make.
Henry came because he loved the challenge of New York and putting the Red Bulls on the map.
"There is a common thread with each one of these guys that we've talked to," Leiweke said. "Which is they absolutely want to come and make a difference. And there's a character about them and a personality about them where they love the challenge of Major League Soccer.
"Not every player is going to have that maturity and that understanding of the role they have to play here. I don't know Wayne Rooney so I can't tell you whether or not he fits that role and it would probably be inappropriate of us to make that judgment on a guy we've never met."
Former designated player Torsten Frings relished his time in Toronto in part because of the anonymity he enjoyed away from the pitch, compared to the tabloid fever in his native Germany.
Leiweke tried to bring Frank Lampard to Los Angeles and says one of the attractions for the veteran Chelsea midfielder was getting his life back in North America after enduring the spotlight in London.
Much to Leiweke's disappointment, Lampard elected to stay in England.
But the MLSE president says successful DPs cannot stay in the shadows.
"There has to be a unique personality here, they have to have a little charisma. They've got to be a star and they have to want at least attention and ultimately the ability to make a difference. And that means they can't go into the quiet of the night, they're going to have to be a star."
Uruguayan World Cup star Diego Forlan has been linked to Toronto. Leiweke made no mention of the charismatic forward, currently playing for Internacional in Brazil, other than to briefly comment when told Forlan ranked 99th on the Guardian newspaper's 2012 list of the top 100 players in the world.
"Thank God, he made it," he said dryly.
Asked if he will get his man, whoever it is, by the end of the current transfer window, Leiweke talked of keeping the door open.
"It may be this window, it may be the next window. We have to find the right person. We are committed to spending the money, the owners have committed to that.
"That's the good news. There's no lack of resources here. That said, 1) we've got to find the right player and 2) he has want to come and then 3) we've got to make a deal.
"And those three are tough. All three of them combined, I truly believe there's only 10 to 12 people you're talking about here. Take your list of 100 and the problem is 90 of them are under contract and they're not going anywhere. So that leaves 10. And of those 10, they've got to fit those three qualities: the character, the desire and the financial ability to get them out of their current deal."
"We're not the only ones fishing," he added.
Toronto had three designated players last year in Frings and strikers Eric Hassli and Danny Koevermans.
Only Koevermans remains with the team. Frings retired and Hassli was traded away.
The 34-year-old Dutch forward, who has 17 goals in 30 games in an injury-plagued MLS career, makes US$1.663 million this season. Under MLS rules, only $368,750 of that counts against the $2.95- million salary cap.
Argentine midfielder Matias Laba, a newcomer this year, is termed young designated player for TFC. Only $200,000 of his salary counts against the cap.