Leyland's boss, Tigers owner Mike Ilitch, also owns the Red Wings. They're in the finals for the first time since 2002. Leyland has frequently expressed his gratitude and appreciation for Ilitch and the way he allowed the Tigers to make the moves they felt they needed.
On the other hand, Leyland is a Pittsburgh resident who attended some Penguins games over the offseason with former Tigers first baseman Sean Casey, who is a Penguins season ticket holder. They're in the finals for the first time since 1992.
It's an exciting matchup for fans around the league, but not the best matchup for Leyland. So when a reporter asked him about it, Leyland tried to be diplomatic.
"That's obviously a no-win situation for me," Leyland said. "I have no comment. May the best team win."
Later, though, he allowed some appreciation for the situation his organization is in.
"The political answer," Leyland said, "is I'm rooting for the guy who signs the checks."
Casey talked earlier this year about attending a hockey game with Leyland, and how intense he gets about the games.
"He was so nervous that he was chewing his fingernails," Casey said of Leyland last month to Booth Newspapers. "I said to him, 'You want some nachos with those fingernails?'"
Given Casey's enthusiastic nature, though, Leyland could say some of the same things about him.
"Casey gets a little excited," Leyland said.
The fact that the Red Wings have gotten this far has taken some of the attention off of the Tigers. Considering the Tigers' struggles so far, even Leyland admits that's a good thing.
"I would say right now," Leyland said, "that [Red Wings] coach [Mike] Babock is doing a pretty good job of saving our tails over here."
Jason Beck is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.