This story was excerpted from Alex Stumpf's Pirates Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.
PITTSBURGH -- Shortly after Derek Shelton was hired as the Pirates' manager in 2019, he started getting phone calls from an unknown Detroit number. He ignored the first couple of calls, but about the fourth time, he decided to answer.
“Hey, this is Jim Leyland,” the voice on the phone said.
“I kind of sat up like my dad had called me,” Shelton said.
Leyland had two reasons for the call. The first was to offer his congratulations to Shelton on his first managerial gig.
“I wanted to let him know how much he was going to enjoy it, what the city meant to the Pirates and vice versa,” Leyland said. “I told him it was going to be a good gig for him. I think he's found that out. He's become a Pittsburgher real quick.”
The second was to ask if Shelton wanted to grab breakfast before he was formally introduced by the club. Of course, he accepted. That breakfast wasn’t a one-time offer, either. About every three weeks, the two go to the Chartiers Country Club to talk ball. Sometimes other coaches -- like Mike Rabelo and Don Kelly, who played for Leyland when he managed the Tigers -- will come, but plenty of times, it’s just the Pirates managers of past and present.
The conversations aren’t so much about strategies or Xs and Os; Leyland feels Shelton has that covered. Instead, it usually revolves around subjects like dealing with players, the media and the responsibilities of the job.
"I know what he's going through on a daily basis,” Leyland said. “The manager's chair can get a little lonely when things aren't going too well. He handles it very well."
Leyland handled the pressures of the chair better than almost anyone in his 11 years as Pirates manager from 1986-96. He then moved on to manage the Marlins, Rockies and Tigers, winning three pennants along the way, as well as a World Series ring with the Marlins in 1997. He’s one of the most memorable characters of his era, and in July, he’ll be inducted into Cooperstown as part of the National Baseball Hall of Fame and Museum.
When Leyland was a young manager, he didn’t have many mentors he could look up to outside of Tony La Russa, who he coached under with the White Sox. He wanted to give Shelton a feel for Pittsburgh and how passionate the fans can be about their ballclub when he took the job. Four years later, they still have breakfasts because they’ve developed a friendship.
Those morning meetups also let Leyland stay better connected with the game. He is a special assistant with the Tigers now, but having that relationship with a big league manager allows him to get a better feel for new analytics and coaching techniques. As Leyland puts it, he’s old, not old school.
“He is a curious learner,” Shelton said. “At [79 years old], he still asks me questions about why we’re doing things and how we’re doing things. He’s notorious for, ‘I don’t care if you want my opinion. I’m going to give it to you,’ and he gives it back to me. It’s beautiful because the way he looks at the game is why he’s in the Hall of Fame.”
"It's changed a little bit, but it hasn't changed for the better or the worse,” Leyland said. “It's still baseball. It's still about catch it, throw it, hit it and come here every day to beat the other team. A lot of things have changed, but a lot of things haven't changed."
One thing that likely won’t change in the coming years are those morning trips to Chartiers.
“I've really enjoyed it,” Leyland said. “We've become friends. I pull hard for him."