Jimmy Devellano certainly did.
"One of the guys that I always tried to make a pitch for late in his career, I tried three or four times, was to acquire Raymond Bourque," Devellano said Monday morning during his Hockey Hall of Fame media availability. "He was getting a little older but I knew he could still play. He'd be terrific under Scotty Bowman for a few more years. I thought we could win a Cup with Raymond Bourque."
The former Detroit GM, set for induction into the Hockey Hall of Fame on Monday, said he kept trying but realized after a while that the Bruins would never trade him to Detroit.
"We had had some squabbles with Boston over the years, mainly because they thought we spent too much money," Devellano said.
Devellano was being polite. What he didn't want to mention, but which is pretty common knowledge elsewhere, is that Bruins owner Jeremy Jacobs and Red Wings owner Mike Ilitch had quite a feud running for a while, which boiled over in a heated argument at a Board of Governors meeting. Trade Bourque to Detroit? Over Jacobs' dead body.
"So what do they do? They trade him to Colorado and they win another Cup with Bourque," Devellano said, laughing. "So we kind of got screwed twice by guys going to Colorado. Patrick Roy first, and then Ray Bourque. But in between we were able to squeeze in a few Cups, so that was good."
Devellano did his fare share of winning with both the Red Wings and New York Islanders dynasties, winning four Stanley Cups with each franchise in various front-office roles.
"In the mid-80s I traded Kelly Kisio to the Rangers for Glen Hanlon," Devellano said. "That really worked out well for us. Glen gave us solid goaltending and we were able to go to the final four in back-to-back years."
But his best one was probably acquiring Brendan Shanahan from Hartford in October 1996.
"We were starting to look like a Stanley Cup team," he said. "Keith Primeau wanted out of Detroit badly, so [we] made quite a big trade. We traded Primeau, Paul Coffey and a first-round pick [Nikos Tselios] for Brendan Shanahan [and Brian Glynn]. And that turned out maybe to be as good as a deal as we ever made."
In 1993, Devellano also made a critical decision that helped crystallize Detroit's modern-day winning ways. The Wings needed a new coach.
"There was a lot of talk that Mike Keenan was headed our way and I went to ownership and really discouraged it," Devellano said. "I was asked by my owner, 'Well, what do you want me to do? I need a coach that can help us win in the playoffs.'
"My answer to Mike Ilitch was, 'Let's hire either Scotty Bowman or Al Arbour.'
"He looked at me and said, 'Go get one of them.'
"I said, 'Which one do you want?'
"He said, 'I don't care. Bring either one of them.' We got Scotty, and the rest is history."
Devellano was clearly humbled by Monday's events. The Toronto native said he used to come to the Hockey Hall of Fame and spend hours reading the plaques of the inductees. Now he's one of them.
His success in Long Island and Detroit made him a no-brainer decision for the Hall of Fame selection committee.
"People say, 'What makes you successful?,'" Devellano said. "I'll tell you what it is: good hockey players. With the Islanders it was Denis Potvin, Bryan Trottier, Mike Bossy, Billy Smith. With the Red Wings, it's been Steve Yzerman, Nick Lidstrom, Brendan Shanahan; I could go on and on ...
"It's been a lot of fun."