Two days after last February's Super Bowl, I met Tim Leiweke for coffee.
In the months since he'd announced his intention to resign as president of Maple Leaf Sports and Entertainment, he'd bounced between moods. At first, anxious to get going; after several weeks, resigned; on this day, re-energized about work still to be done.
"What are you doing?" Leiweke asked as he sat down.
I was doing something stupid – responding in detail to someone who'd ripped my column from the day before. I'd mounted a defence of Seattle Seahawks coach Pete Carroll and the disastrous pass call that briefly made him the most talked about man in the Western Hemisphere.
I apologized, said I'd just be a second and kept typing.
Leiweke's BlackBerry rang. He looked down and turned it around to me. The caller ID read "Pete Carroll," He answered, grinning.
"Hey Pete, I'm sitting here with a writer from Toronto. He said what you did was the right thing and …"
Leiweke stood up and walked away. A few minutes later, he returned.
"Why is Pete Carroll calling you right after the Super Bowl?"
"He called me the day before the Super Bowl," Leiweke said, outrageously pleased with himself.
After 2 1/2 eventful years in Canada, he's returned to Los Angeles. It's hard to believe anyone in this country will ever be better connected. Leiweke, 58, knew everyone who mattered, and wanted to know everyone who didn't. There wasn't a hallway in the world he could walk down without shaking hands with a half-dozen anonymous passersby.
Leiweke had nothing but friends, until he arrived in Toronto.
He came here to push MLSE to another level, and did. But with an expiry date.
He wanted to build something of his own
Leiweke built the bulk of his reputation as the president and public face of Anschutz Entertainment Group. AEG may be the largest sports concern in the world – building and managing arenas around the globe, owning teams such as the Los Angeles Kings.
In the latter stages of his time there, Leiweke became preoccupied with bringing the NFL back to L.A. When that plan went sideways, he parted ways with AEG's mercurial owner, Phil Anschutz, in early 2013.
Leiweke says there was no non-compete clause. He wanted to begin building something of his own. But he was advised he'd face legal problems if he started a business that looked too much like AEG – and AEG has so many facets, it looks a little like everything.
Leiweke's lawyers told him to wait a bit. He began casting about for something to occupy his time.
Leiweke knew MLSE principal Larry Tanenbaum through the NHL and Major League Soccer boards of directors. They were friendly, but not friends. Tanenbaum approached him about taking the top job, which had lain vacant for several months.
"I was intrigued by the idea of Toronto, living in a different country, and all the teams, and saw a lot of upside. It was a good fit," Leiweke said.
In spring of 2013, Leiweke met several times with the Capulets and Montagues of the MLSE board – BCE CEO George Cope and then-Rogers CEO Nadir Mohamed.
Leiweke understood that relationship might be fraught, but he wasn't worried.
"We're not a big piece of their world. At the end of the day – at least until now – they've all been very civil. There's stress, but I work below those levels," Leiweke said at the time.
Cope and Mohamed gave Leiweke the high sign. He signed a deal. There was a gradual unveiling. What was not publicized was that he did not intend to stay long.
"They wanted to know that I would be here for at least two years. I didn't want to make that commitment because I didn't know where this path would take me … This was always my decision."
In the end, it was agreed that Leiweke's bonuses would be clawed back if he left before 24 months had passed. Not everyone on the board was aware of the proviso.
"Some of them were caught off-guard when I said I wanted to go create my own company, but some of them knew it," Leiweke said. "George [Cope] is disappointed I'm leaving because I think he feels like maybe I let him down a little bit."
After Rogers won the national NHL TV rights deal, relations between the telecom companies progressed from hostility to open war. Mohamed was gone, replaced by combative Brit Guy Laurence. (Leiweke describes Laurence's management style by leaning in and sticking both middle fingers in my face – "That's Guy." He says it approvingly.)
Leiweke is well aware that he is incapable of treading lightly. Every idea is the greatest idea ever, and must be shouted at top volume to anyone who will listen. When he is up, Leiweke is an elemental, irresistible force. He has many enthusiasms, and they tend to run into each other.
In his first interviews, he said he'd already walked the parade route for an eventual Leafs Stanley Cup victory. All the scolds in the city – and they are in the majority – lampooned his excitement.
"What I didn't know is that there was a standing joke about the Leafs and planning a parade route," Leiweke shrugged. "Go look at what I said about the parade, which was that I dream about it every day. What executive in his right mind doesn't dream about success?"
Having got used to a string of vanilla executives, Toronto didn't know what to make of this slick visitor. He was instantly a love/hate proposition. That tension flowed up, as well as down.
"I probably should have fit in better to the culture, rather than thinking the culture was going to fit better around me," Leiweke sighed.
"He made one mistake while he was here," former Blue Jays president and friend Paul Beeston said. "He didn't own the company."
Leiweke was in a hurry, and pushed forward an accelerated agenda. He tore down and rebuilt the executive structures of three teams. He renovated BMO Field, and got approval to build a new Raptors training facility nearby. Using Jon Bon Jovi as a front man, he tried to lure the NFL to Toronto. He planned to surround a new stadium with a multibillion-dollar development.
In essence, Leiweke wanted to remake the city.
All this ambition was bound to rub some of his bosses the wrong way.
He claims he was able to significantly increase revenues – though he won't say by how much. He does have the habit of making money easily.
During one conversation, Leiweke paused briefly to tap off a message to a contact in the concert business about booking an extra night for Fleetwood Mac at the Air Canada Centre.
"That's a nice parting gift – $500,000," Leiweke said. "I'd like to see the next guy do this."
Rogers and Bell were happy to see their investment thriving. Executives such as Cope and Laurence have little interest in the day-to-day doings of the Leafs or Raptors.
Not so for Tanenbaum. He is a regular presence around the clubs, taking a keen interest in the players' lives. One of Leiweke's first acts was finessing Tanenbaum away from making post-game appearances in the locker rooms.
However much he wanted to separate church and state at court level, Leiweke was incapable of keeping himself out of the news. He was one of the first public figures to pick a fight with then-mayor Rob Ford. In a speech, he called Ford "Tommy Boy," after the goofy Chris Farley character. When Leiweke eventually met the Ford brothers, they referred to him derisively as "Timmy Boy."
He was attracting attention, and upending many corporate apple carts.
"This was tough on Larry. I went through a lot of changes," Leiweke said. "I did some damage to that relationship."
There were moments of high, and possibly even reasonable, paranoia. Leiweke did not speak loosely in vehicles provided by MLSE's car service, for fear that what he said was being funnelled back to Tanenbaum.
He was also a beneficiary of that eavesdropping. It was one of the drivers who told him soccer star Jermain Defoe wanted to leave Toronto. Defoe's mother, Sandra St. Helen, had been yelling about it on the phone.
Despite being the third of MLSE's big-three clubs, Toronto FC created the most tension in the executive suites.
Leiweke persuaded the board to commit to a $100-million odyssey to sign Defoe and American star Michael Bradley. By the time he got off the plane, Defoe already wanted to go home. Midway through his first year, he 'injured' himself and flew back to London.
Leiweke realized he'd orchestrated a disaster, and wanted to tie off the wound by selling Defoe. Tanenbaum went directly to the player. Defoe flinched, insisting he wanted to stay.
Leiweke and Tanenbaum began to argue about whether to sell Defoe during the 2013-14 Christmas transfer window.
"We got a very, very good offer. We should have sold him," Leiweke said. "I got overruled. They made a huge mistake."
Tanenbaum won the argument, but Defoe would still be sold a year later.
As things got uglier, Tanenbaum took the remarkable decision of stripping Leiweke of his corporate seats behind the Maple Leafs bench. Leiweke said he preferred to sit with the hockey execs in the gondola in any case. Rogers's heir and MLSE board member Edward Rogers got wind of the pissing contest and intervened. Tanenbaum cooled.
At the 2014 home opener, Leiweke was in his familiar spot, sitting beside daughter Francesca.
This had all been exacerbated by the manner in which it was decided Leiweke would leave. News leaked in August, 2014. Leiweke played a semantic game, denying he was going, but failing to mention that he intended to at some point. The board called an emergency meeting. It was decided Leiweke would announce that he would depart the following year. He'd been hanging on ever since.
"Was there friction and tension? Yeah. I've only been here two years. I made a lot of changes. I caused a fair amount of havoc," Leiweke said. "Obviously, everyone's feeling that on my way out and I understand that."
After the Defoe spat, Leiweke and Tanenbaum resumed an amicable business relationship. Both were preoccupied with bringing the Toronto Argonauts into the MLSE/BMO Field nexus – that helped things.
Through an MLSE spokesperson, Tanenbaum declined comment for this story.
"I am preoccupied with leaving this well," Leiweke said in the midst of his lame-duck phase. As he was getting set to go, Leiweke was trying to figure out what he wanted to do. Primarily, he wanted to own something.
"I can't work for anyone ever again," he said.
At one point, he flirted with a group of Qatari investors, in a plan to begin acquiring sports clubs worldwide. That fizzled.
When the deadline for his departure passed in June, 2015, he continued to run MLSE. However, he was no longer an employee of the corporation. Instead, MLSE became the first client of his new venture, Oak View Group. For months, the biggest sports concern in Canada has been run day-to-day by a functional consultant.
With Oak View, Leiweke has partnered with Madison Square Garden and New York Knicks owner James Dolan and talent manager Irving Azoff. MLSE is still a client. Leiweke's first major venture is helping retired soccer star David Beckham build a stadium in downtown Miami to house his MLS franchise. Leiweke is an investor in that team as well.
Speaking from Florida on Thursday, Leiweke was back in a ruminative frame of mind.
"I actually miss the city [of Toronto]," he said. "That's something that surprised me a little bit. I miss living there."
He continues to speak fondly, if distantly, of the company he pushed so hard.
"[New MLSE CEO] Michael [Friisdahl] will have a different style than me. He's less of a bull, which I think is a good thing," Leiweke said. "We made some tough decisions. We made some bold pronouncements. They got me in trouble, but we had to learn to not be afraid to win."
It's hard to say yet what his true legacy is – it will continue spinning out under the lieutenants he put in place to run the Leafs, Raptors and Toronto FC.
What he did was create an intoxicating sense of possibility in a country unused to this sort of loud American vigour.
At heart, Leiweke is a salesman. A few in Toronto may not have bought into his vision for the city. But you could not turn away from the pitch.
Successful or not, Tim Leiweke's time as president and CEO of MLSE was anything but stale. Here's a rundown of the legacy he left behind.
May, 2013: Masai Ujiri is hired the new general manager of the Toronto Raptors.
September, 2013: Drake joins the Raptors as a global ambassador.
September, 2013: Tim Bezbatchenko joins Toronto FC as general manager, replacing Kevin Payne.
January, 2014: Toronto FC acquires Michael Bradley from A.S. Roma and signs superstar striker Jermain Defoe from Tottenham, laying the groundwork for the "Bloody Big Deal" marketing campaign.
February, 2014: Leiweke outlines a plan for renovations at BMO field and the desire to attract an NFL team to Toronto.
April, 2014: Brendan Shanahan is appointed president of the Toronto Maple Leafs before facilitating an organizational tear-down conceived by Leiweke.