A self-proclaimed hockey nut, Boudreau grew up a die hard Maple Leafs fan. He played for the Marlies and the Leafs and knows about as much about the history of the club as anyone.
He recently took interest in a list published by The Hockey News, which put out a special issue with its Top 50 Players for every franchise in the NHL.
While back in Toronto, Boudreau took a trip down memory lane, analyzing the list of Maple Leafs that made the cut, even mentioning a few that missed it.
As expected, many in the top 10 of The Hockey News' list are from the Leafs' early years, even pre-dating Boudreau.
The No. 1 player on the list, Syl Apps, played from 1936-48 and was a five-time All-Star who played nine seasons, as his tenure was interrupted by service in World War II.
"He was before my time, but from all accounts, he was a great Maple Leaf," Boudreau said.
No. 2 on the list, Charlie Conacher, was also before Boudreau's time but Tim Horton, the No. 3 man, played more than two decades in Toronto, including during Boudreau's childhood.
"Tremendous defenseman, but I don't know if I would have thrown him up there as high as that," Boudreau said, pointing further over on the same page to the No. 6 player on the list, Borje Salming. "I played with Borje and he was as good a player as there ever was."
Of the top 10 players on the list, six came from the era of the 1960s or earlier, a time when the Maple Leafs were hockey royalty. Toronto won 13 Stanley Cups between 1918 and 1967, but hasn't won one since.
Boudreau was 12 the last time the Maple Leafs won a Stanley Cup more than 50 years ago.
"I think this [list], they're really looking at the 40s, 50s, and 60s and trying to take the Stanley Cups that the Leafs had then and say they were great players, even though there were only six teams in the League," Boudreau said.
Turning the page, Boudreau's eyes light up as some of the players of his era begin to make appearances.
Darryl Sittler, a 12-year Maple Leafs veteran from 1970-82 was a teammate of Boudreau's at No. 11 on the list.
"In today's world, he'd be making $10 million a year," Boudreau said. "He was a great offensive player, very dedicated and could fight. He was tough. He was the total package."
One spot below him is George Armstrong, who began his career with the Maple Leafs in 1949 and retired in 1971, having played in four different decades. He then coached the Toronto Marlboros three separate times during the 1970s, two of those years with Boudreau as a player.
"Greatest captain I ever met," Boudreau said. "When he was my coach, he was a person you'd go through a wall for."
Armstrong was just one of several players on the list who would go onto coaching careers in Toronto. The No. 18 player, Bob Pulford, and No. 25, Red Kelly, each coached Boudreau at one point during his career.
"I take a lot of pride in being able to say I played with these guys or I knew who they were," Boudreau said.
As the list moves further, some of the more modern Leafs start to make an appearance. At No. 19, former Leafs captain Doug Gilmour, who owns the franchise record for points-per-game, makes an appearance.
"When he came in the 90s, he was a consummate work-a-holic," Boudreau said. "I wore No. 19, he was small like I was but his attention to the defensive part of the same and his work ethic was second-to-none and something I wish I had."
The first modern player on the list is Mats Sundin, who at No. 10, is the only player among the top-25 Leafs to have played a bulk of his career in the 2000s.
Boudreau had the unique experience of coaching against him at the tail end of his career, but followed him closely as a coach in the AHL.
"In coaching against him, what bothered me was, anytime the Leafs needed a goal late in the game, he got it. He got it all the time," Boudreau lamented. "It was tough."
Scanning the final 25 players on the list, Boudreau ran into a few more familiar names.
"Ron Ellis (No. 31) was my linemate. No. 32, Rick Vaive, he was the only Maple Leaf to score 50 goals twice and he's No. 32. He's never gotten the respect he deserved. I don't know why the Toronto people didn't like him. He was a great player.
"I don't think Tomas Kaberle (No. 35) should be on that list.
"Lanny McDonald (No. 39) would be higher on that list but he wasn't here long enough I don't think. He was a victim of [former Maple Leafs General Manager] Punch Imlach trying to show everybody who was boss, and it didn't work.
"Ian Turnbull (No. 47) was an unbelievable talent but was a little too free spirited, but a great player that I played with.
The first name snub of the list, at least in Boudreau's mind, is his good friend and current Wild assistant coach John Anderson, who played 534 games for the Maple Leafs from 1977-85, scoring 189 goals and 393 points in those games.
"I can't believe he's not on here," Boudreau said. When I'm looking at some of these guys and you're looking at John Anderson and Bill Derlago (another omission from the list), these guys were great Leafs."
