There were times, too many of them to remember, when all this seemed too far-fetched even to be imaginable.
Like when, as a scrawny kid from the wrong part of East L.A., he was too embarrassed by his 98-pound-weaklingness to lift weights with his teammates.
Or when, as a 21-year-old first-year pro owed money by a bankrupt football team that inauspiciously held its inaugural training camp on a Las Vegas parking lot, his best option was to wait tables.
So Anthony Calvillo did, for six months, at a now-defunct eatery in Hawaii called Rodeo Cantina. If you're going to be a waiter it might as well be on a pier in Honolulu.
The memories of hard graft stayed with him.
"After that, I became the best tipper in the world," Calvillo said.
It's a fortunate soul who at age 40 can claim never to have held a workaday job.
Other than his brief interlude at the sweatier end of the restaurant business, Calvillo reckons he is that guy.
While the Alouettes (4-3) prepare for Thursday's tilt against division rival Hamilton (3-4), Calvillo is thinking about football, but also about a milestone birthday that will see him join a select club of 20 or so men who were pro quarterbacks into their fifth decade.
"I may be 40, but I'm still playing football, the same sport I've been playing since I was five years old, so I don't feel like a 40-year-old whatsoever," he said.
Part of that has to do with Calvillo's off-field regimen – his cluttered locker in the Als' dressing room looks like a cross between a health-food store and dietician's lab.
There are plastic tubs of organic preworkout powders, postworkout powders, during-workout powders, protein powders, amino acids, coconut oil, organic oatmeal pouches ("my breakfast every day").
There's a jar of cashews and a package of puffed-corn cakes.
"The other guys say they taste like cardboard," he laughed. "The good thing is they won't come in and take my food."
Calvillo's teammates have gently ribbed him about his age this week – this is not a man who is the butt of many jokes – but there is clearly wonder in their eyes as well.
"It's pretty amazing, man, being able to keep yourself in shape that long, but it shows other guys what you have to do," said injured wide receiver Jamel Richardson, who is a decade younger than Calvillo (Richardson burst out laughing when asked if he thought he could play until 40).
Diet has become an essential component to Calvillo's longevity. And there have been happy by-products off the field, such as early diagnosis in 2010 of a cancerous thyroid.
Calvillo's underrated competitive drive and his zealous attention to detail – he works famously long hours dissecting game film – are also defining characteristics.
It wasn't always thus.
"I was lazy, very lazy, didn't work out much at all ... I wasn't very disciplined. In terms of lifting weights, I was always embarrassed to lift weights because I could not lift anything," he said. "Whenever the guys went in there I would somehow manage to avoid it, and they allowed me to do it."
Somehow, he is now 19 years into a career in which he has set the pro football record for yardage and a CFL record for completions.
It's probably safe to assume he won't stick around as long as George Blanda, who finally retired from the NFL at 48 – but Brett Favre's touchdown record 508 might not be out of reach. Calvillo enters the game with the Tiger-Cats tied for second on the career list at 435 with Warren Moon.
Calvillo has said semi-seriously that he would like to end his career at .500 in Grey Cup games (he is 3-5), and anyone who watched him pass for four touchdowns last week won't bet against it happening.
Should Calvillo top 300 yards passing against his one-time employer on Thursday, it will be the seventh successive time he has done so this season.
Alouettes head coach Marc Trestman, a well-established quarterback guru whom Calvillo credits with extending his career, said the mere fact that his pivot is still around after so many years is a towering achievement.
"[A quarterback's] is a very, very difficult life in terms of what has to be done on and off the field, and to do it for so many years at such a consistent level, it's almost incomprehensible," he said. "I think the most important thing to do with Anthony Calvillo is stop and appreciate what we all have ... we should just enjoy the moment."