Former Whitecaps Manager and major league pitcher Phil Regan is no stranger to this area.
The Grand Rapids Sports Hall of Famer has ties to both teams, but is only rooting for just one in this year's World Series.
Phil Regan never though he'd see the day.
"No," he laughed. "If you had a crystal ball, I don't think you could see that. The Cubs, you kind of figured the way they played all year that they had a pretty good chance of getting in there, but Cleveland who would have thought that?"
Regan, now a New York Mets minor league staffer, spent some of his best pitching years with a team some know as the most celebrated second-place team in the history of baseball, the 1969 Cubs.
"The fans were so taken with that club and it was so exciting and it looked like finally we were going to win something," Regan remembered. "By August we were leading the league by 8 1/2 games, we were beating the Mets.
"Then the Mets caught us and went on and of course won the World Series."
Once retiring from playing, Regan spent some time in Cleveland as a pitching coach in 1994 before the players went on strike. Three years later, he found himself back at Wrigley.
"I went back there in 1997 and the Cubs didn't really have much of a lineup at that time the first year, but the second year, we got into the playoffs that year, we were a wild card," Regan said.
Though they never made it past that wild card game: love, passion, and the league's longest drought has Regan rooting for the North Siders.
"I got to go with the Cubs," he said. "I spent more time there and I think it would be great for the fans there to win a world championship. I guess because you can say its been so long and finally you can say its over."
Regan got his start with the Detroit Tigers. He was then traded to the L.A. Dodgers, where he got the nickname the "The Vulture" for his ability to close games.