Perrotto: Derek Shelton Could Never Find a Better Mentor

It is easy to understand why Jim Leyland and Derek Shelton have become kindred spirits.

Both men got their first major-league manager jobs with the Pittsburgh Pirates after never playing in the big leagues. Both joined the franchise at low points in its history. Both were relatively unknown to the fans when they were hired.

Leyland helped pull the Pirates out of the abyss more than three decades ago, leading them to three straight National League East titles from 1990-92. Shelton is trying to do the same as he gets set to enter his fifth season.

No wonder they have developed a close friendship since Shelton was hired following the 2019 season to replace Clint Hurdle. Shelton even designed a T-shirt last season that depicted Leyland with a cigarette in his mouth and many members of the Pirates’ coaching staff as well as players often wore them in the clubhouse.

“He’s a great guy and he’s a really good manager,” Leyland said. “The Pirates have a good one.”

That is quite an endorsement considering that Leyland will be inducted into the National Baseball Hall of Fame in July after gaining election last month. Shelton was at the Winter Meetings in Nashville last month when Leyland had a press conference a day after learning he was going to be immortalized in Cooperstown.

“So unbelievably excited to be in the room, to watch him talk about it was emotional just because of the fact that he’s meant a ton to me,” Shelton said.

That is not just hyperbole on Shelton’s part.

Leyland and Shelton frequently meet for lunch during the season at Chartiers Country Club. Sometimes they are joined by Pirates bench coach Don Kelly – who played for Leyland with the Detroit Tigers – and third base coach Mike Rabelo. Leyland’s son Patrick, a manager in the Chicago White Sox’s farm system also shows up occasionally.

“There’s no better sounding board,” Shelton said. “If you’re the manager of the Pittsburgh Pirates, to be able to call Jim Leyland at a moment’s notice, to be able to have breakfast and talk through different things that are going on and how to do it, for him to tell me what he thinks I’m doing well and what I’m not doing well. He’s very transparent with me, which I really appreciate.”

Leyland last managed in 2013, retiring after leading the Tigers to the American League Championship. He is now a special adviser to Tigers president of baseball operations Scott Harris.

What strikes Shelton about Leyland is that the 79-year-old remains forward-thinking.

“He’s not old school because he understands what’s going on,” Shelton said. “He has thoughts and will ask questions about why things happen, but he’s always learning, and he’ll ask me questions of like why did you do this or why did you not do that, and then he’ll tell me what he thinks I did wrong, which is beautiful.

“I think he means a ton to me personally because he’s someone that is you know filtered in terms of the feedback that he gives me.

The paths of Shelton and Leyland crossed on the baseball trail over the years. However, they were more acquaintances than friends when Leyland reached out to Shelton in 2019.

Like many stories involving Leyland, there is humor involved.

“When I first got the job, there were four or five days between when I got the job and when we had the press conference,” Shelton said. “It kind of broke that I got the job. I kept getting this call from a Detroit number and didn’t answer it. Finally, I was at dinner one night and sitting with my wife and some friends, and I may have had a glass of bourbon or two, and I said I’m going to answer this damn call.

“And I answered it, it was like this gruff, ‘This is Jim Leyland.’ Oh, wow. I stood up. He invited me to breakfast the first morning I got to Pittsburgh. Just told me about the city and told me about what the expectations and told me about basically talking to (the media) guys in the city and how it was.”

The two baseball lifers immediately hit it off and have now developed a strong bond, which — in Shelton’s words — is a pretty cool story.