Alan May’s HockeyDB profile looks like the departures board at the Greyhound Station. He was that kid who left his Edmonton high school to play Jr. A hockey for the Estevan Bruins, and even his buddies back home (full disclosure: I was one of them) could barely believe that someone had duped Al into thinking he should pursue a career in hockey. And he proved us all wrong.

Years later, through 393 National Hockey League games—and another 359 in the minors with teams like the Atlantic Coast League’s Carolina Thunder, the New Haven Nighthawks and, finally, the Abilene Aviators—Al May has accomplished one thing in hockey career that no other man could. From Gordie Howe to Wayne Gretzky, from Gary “Suitcase” Smith to Brent Ashton and Mike Sillinger, nobody was ever traded more times at the National Hockey League trade deadline than May’s four.

“Every year, even after I’d finally made it and was playing full seasons in the NHL,” the undrafted native of Barrhead, Alta., says, “that deadline would come, and it would be, ‘Oh no. Oh no…'”

So how does one become, ahead of more than 5,500 players in the history of the league, the one player who was dealt at the deadline more than anyone else? Well, for May it began with the Maine Mariners and a hot streak back in 1988. Edmonton had sent goalie Andy Moog to Boston in return for Bill Ranford and Geoff Courtnall earlier that March 8 deadline day. May for Moe Lemay was basically an addendum to that trade, and the Oilers thought they were getting a steal.

“(Maine head coach) Mike Milbury had told me a couple of weeks before, ‘Slow it down,'” May says. “I’d found a groove in the AHL. (Edmonton scout) Ace Baily had been following us around. One day, we’re in Newmarket and Milbury comes pounding on my hotel room door. He starts yelling at me for not listening to him. I had four games in row with a goal, I’m fighting every game, and Ace had been following us. ‘You mother f—-r, you’ve been traded,’ Milbury says to me. ‘You didn’t slow down.'”

The problem was, the dearly departed Ace Bailey had given his GM, Glen Sather, some bad info. “Slats thought I was 6-foot-4, 240 lb.,” May says. “I got on the phone with him, and he says, ‘How much do you weigh?’ I said, ‘185 lb. on a good day.’ At the start of the phone call I was on my way to Edmonton. By the end, they were having problems getting me there. I was starting in Halifax.”

May couldn’t play for the 1988 Oilers and he knew it. By the ’89 deadline he was sitting on the farm in Cape Breton with his bags packed. “When (coach) Ron Low called to say I was traded, I was at the airport and ready to go in a half hour,” he remembers.

The Oil dealt May at the ’89 deadline to Los Angeles along with Jim Wiemer for two nobodies—John English and Brian Wilks. But by 1994, after another trade to Washington for a fifth round pick, May had established himself as a scrappy NHL fourth-liner. His new coach in Washington, John Schoenfeld, didn’t agree however, and as the ’94 deadline loomed, Caps GM David Poile called May into his office. “David was such a decent guy,” May says. “He said to me, ‘Ownership wants me to re-sign the coach, and I see you two aren’t exactly getting along. Is there anywhere in particular you’d like to go?'”

May was off to Dallas at the ’94 deadline along with a seventh-rounder for Jim Johnson. That lasted a solid year. “One day we’re in Anaheim at a morning skate—just the scrubs,” May says. “We get back to the hotel and someone says, ‘(GM) Bob Gainey wants to talk to you right now.'”

It was April 7, 1995. The dreaded Deadline Day.

“Bob opens the door of his hotel room, doesn’t even invite me in,” Mays says, “and he says, ‘You’ve been traded to Calgary. Thank you.’ End of conversation.”

It was May for an eighth round pick.

The returns were diminishing. May would not spend another NHL trade deadline in the NHL. A career in which he squeezed every drop from the lemon would soon conclude. “You know, every draft pick I got traded for was a draft pick that was never spent on me,” May says. “That’s how I looked at it. When I got to Calgary they had four or five guys who played just like me: Sandy McCarthy, Ron Stern, Paul Kruse… A bunch of guys who took bad penalties. Every game I got to play I’d stand in front of the mirror and look at myself, thinking, ‘This could be the last game I spend in an NHL jersey.’ I was 30 years old. I felt like the end was near.”

Today May, 49, works as an analyst on Capitals games for Comcast SportsNet Washington. And he’s a lot less stressed out by the trade deadline.