Having managed the Pirates to three division championships in his 11 years in Pittsburgh, Leyland was also at the helm for the first four losing seasons of this streak. He left after the 1996 season and went on to manage the Marlins to a World Series title the following season.
Leyland, a Perrysburg, Ohio, native, still makes his home in Pittsburgh in the offseason but admitted that the Pirates' recent history has forced him to create some distance from the organization.
"No question about it, it breaks your heart," Leyland told Detroit reporters on Saturday. "I was there for the tough times when I got there, then I was there for the good times, then I was there for the tough times again when they just tore it all apart. So I've seen both sides of it.
"But we drew 2.6 million [fans] in Pittsburgh. A lot of people don't know that. You put a good baseball team in Pittsburgh, they'll come out. It's a Steeler town, but they'll come out. And I think they do have some good-looking young players now. You keep saying, 'Finally,' but it's just, I don't know. I don't stay close to it. I try to stay away from it. But it breaks your heart."
The Pirates' downswing began after Leyland's team lost Game 7 of the 1992 National League Championship Series to Atlanta in dramatic fashion. That offseason, Barry Bonds and Doug Drabek left to follow free-agency dollars and Pittsburgh finished 75-87 the next year.
Leyland still sees the Pirates a couple of times each Spring Training, and he got a few regular-season looks this year, too, with Pittsburgh traveling to Detroit for a June Interleague series. Leyland said he has felt encouraged by some of what he has seen recently.
"They have one of the best young players in baseball now, [Andrew] McCutchen," Leyland said. "He's good. He's really good. And they've got that [Pedro] Alvarez kid. So they've got something, but you don't know. Their track record has been they get good [players] and they don't sign them. They let them go. They either trade them or they let them go.
"Now, is that going to continue? I don't know. I think they are stocking their farm system a little better. I just saw they signed their No. 1 pick. They've got arguably the best stadium in the country."