The notion we might talk again seems so far-fetched, at the start Leaf admitting to being "very apprehensive," but saying, "I was a phony person for so long, it's so freeing now to tell the truth."
The recovering addict -- 33 now, repentant, trying to make amends and yet eager to still make a difference with the rest of his life -- is a few days removed from being sentenced to 10 years of probation on eight felony drug charges.
It's also only days now before the next NFL draft when his name will be bandied about again as the all-time flop.
"If I'm going to be the biggest bust, I have to own up to it," Leaf says. "I used to go to bed at night hoping somebody else like Heath Shuler might magically leapfrog me on those all-time bust lists.
"It never happened. Why? Because I am No. 1. I can't even think of anyone else in the ballpark that might be close to my combination of disappointment and failed expectations."
He laughs, and I don't recall hearing that before, certainly not as a prelude to something even more unexpected, self-deprecating humor.
"I dodged a bullet," he says. "A strong case can be made that Peyton Manning is the greatest quarterback since Unitas. It's bad enough as it is, but just imagine if I had been picked ahead of Peyton."
The Chargers made Leaf the second choice in the 1998 draft, the move hailed locally because fans finally had a worthy replacement for Dan Fouts.
When Leaf is referred to as a "punk" following a preseason interview that also details a drinking binge, advances on another quarterback's wife and nasty comments about Manning, it's the columnist who hears the criticism.
Later, though, he becomes a lifetime sound bite, yelling "knock it off" to a reporter, his immaturity becoming a headline. The incidents and losses then mount.
"It's all on me and no one else," he says. "I take full responsibility for not succeeding.
"It was total self-destruction. My mom has old tapes. I listened to one recently and cringed. That kid was a punk. That's my fault for leaving college early and not having someone around me to help. And if I did, as stubborn and bullheaded as I was, I probably would not have listened. I was 22, but I was 16 probably as far as maturity goes."
He began to find himself alone in a crowded locker room, his teammates as put off by him as the media. He spent his free time in Las Vegas to escape, hiding later becoming a way of life.
Four years after arriving in San Diego, stops in Tampa, Dallas and Seattle; wrist, shoulder and knee injuries; a total of 25 games, 14 touchdown passes and 36 interceptions; Leaf quit.
"I was tired of being beat up by the media," he says. "I was just so exhausted. I thought I could just walk away, not talk about it and it would all go away, but that's the not the way the world works."
Poor performances, injuries and along the way his marriage of two years to a Chargers cheerleader ends.
"For so many years I just wanted to pretend none of it happened," he says. "I had such a bad feeling about myself, telling no one, and here it was piling up for 10 years. I was in pain, and I knew when I took prescription drugs I didn't feel anything. If you don't feel anything, then you don't have those bad feelings."
He took drugs for a sore wrist in the NFL, hurting it again as an assistant football coach at West Texas A&M.
"I realized one night I was taking drugs for emotional and not physical pain," he says, "but it had such a hold on me. I couldn't ask for help -- I didn't want to appear weak."
When he couldn't get drugs, he tried stealing them, lost his job, faced arrest and became a national embarrassment again.
"If I didn't have such notoriety, maybe it would have been shuffled under the carpet, and I would have continued on the wrong path until I killed myself," he says. "But I'm such a public person, so it got thrown to the media right away. I resented notoriety for so long, but it may have saved my life."
He checked into rehab, spent 42 days in Canada receiving treatment, staying longer to work on anger management.
"It's been 17 months," he says of his sober run. "It's an ongoing struggle, but a positive one."
He now organizes fishing trips for a Canadian resort, and has reconnected with his family as well as with Cougars alumni, who gave him a standing ovation recently at a football dinner.
"Brought tears to my eyes," he says. "I thought I had let them down, but all they want to do is help."
And so it goes, he says, "a lifetime ahead and my name is not going to go away, so why not use it to benefit others?
"I don't know what could be more powerful than me standing in front of young athletes telling my story. I'm no role model, just someone with a story of struggle. And maybe triumph."