PITTSBURGH -- The start of Derek Shelton’s first season as a Major League manager was supposed to play out as if he had written the script himself.

Shelton was going to put on his No. 17 Pirates jersey and take his place in the visitors’ dugout at Tropicana Field, less than 10 miles from his home in Treasure Island, Fla., in front of friends and family. Then he would fly to Wrigley Field in his native Illinois. Then he’d manage his first game at PNC Park, looking out of the home dugout to see a packed house and Pittsburgh’s scenic skyline.

None of it went according to plan. Nothing about this year has. But it almost seems fitting that Shelton’s managerial debut was delayed four months and rescheduled, finally, for Friday night in St. Louis.

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His professional coaching career began 23 years ago. He spent the last 15 years coaching in the Majors. One of Shelton’s mentors once told him that, if he stuck with it long enough, he could be a big league manager. That conversation happened 18 years ago.

“This was the goal,” Shelton said. “Once I started to get into this, I think [Friday] night was what I wanted to do.”

He has waited a long time for it.

The day he was introduced as Pittsburgh’s manager, Shelton described himself as a “very poor Minor League catcher” in the Yankees’ system from 1992-93.

“I’d say he’s a good evaluator of talent,” said former Yankees executive Mark Newman, laughing, “and that doesn’t destroy his reputation.”

Shelton underwent elbow surgery after the 1993 season, ending a playing career that had barely begun. But he made an impression on coaches and executives in the Yankees’ organization. Newman knew Shelton’s father, Ron, who had coached Newman when he was a freshman at Southern Illinois University, where Shelton later played. Newman quickly recognized the characteristics of a coach in Shelton, too.

“He was bright and hard-working, and he had a personality that attracted players to him and coaches -- genuine, authentic, respectful of other people,” Newman said in a phone interview. “His demeanor and temperament as a player were just fantastic. He always did what he was asked to do and really built great relationships throughout the organization.”

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Newman filed away Shelton’s name in the back of his mind, identifying him as a future coach or manager whenever a lower-level position became available. In the meantime, Shelton needed a job.

After his elbow healed, he worked for Dodge Moving and Storage in St. Louis for the better part of two years. He started off loading trucks -- “legit moving,” he said, “which was bad” -- before taking on a role in sales. To this day, he says, one of his rare talents is packing a moving truck with hyper-efficiency.

He returned to baseball after the 1996 season, having weathered the 1994-95 strike and a tough job market the following offseason. He interviewed for a scouting job with the Tigers, but Newman and Gary Denbo called with a better offer to be the hitting coach for the Yankees’ Gulf Coast League team.

“When I was playing, especially when I got into pro ball, I knew I wanted to coach -- just because I realized, talent-wise, that it was not going to work,” he said. “Once I got into coaching in the Minor Leagues, I was like, ‘I want to manage.’”

Shelton quickly worked his way up as a coach for Class A Tampa in 1998 and Double-A Norwich in ’99. He became manager of the Rookie-level GCL Yankees in 2000, led them to a championship in ’01 and won the New York-Penn League title with Class A Staten Island in ’02.

As a young manager, Newman said, Shelton handled the team like he had 10 years of experience.

“He has one of those calming personalities that is at the same time filled with energy, and that’s not an easy combo to pull off,” Newman said. “The Staten Island team was a high-profile deal for us. It was in New York City. Our owner cared a lot about the way those guys did. And he was fabulous.”

One of the pitchers on that 2002 Staten Island team was Justin Meccage, who’s now the Pirates’ bullpen coach. Like Newman, Meccage saw then what many Pittsburgh players have raved about all spring and summer: Shelton’s natural ability to connect with players, no matter their age or ability.

“To this day, I think that's probably still his strength,” Meccage said.

After the 2002 season, Newman told Shelton that he could be a big league manager someday. He showed the appropriate temperament, a desire to continue learning and the right way of dealing with people. He exemplified one of Newman’s favorite phrases in player development: “They don’t care what you know until they know that you care.”

Newman was the first person to predict Shelton’s future. And Shelton didn’t forget it. When he referred to himself as a “very poor Minor League catcher,” he was thanking Newman for always believing in him and putting him on the path to manage in the Majors.

For the next 14 years, Shelton’s ascent was steady and traditional. He went from Minor League player to coach to manager in the Yankees’ system. Then he spent three years as Cleveland’s Minor League hitting coordinator before becoming the Major League team’s assistant hitting coach from 2005-09. His next stop was Tampa Bay, where he served as hitting coach under Joe Maddon and Kevin Cash from 2010-16, an uncommonly long tenure in that position.

The Rays still express nothing but praise for Shelton, with Cash lauding his attention to detail and saying he’s “going to be a star” as a manager. But when Tampa Bay dismissed him on Sept. 6, 2016, Shelton had a hard time seeing himself as a future manager.

That offseason, Shelton interviewed for two jobs. Twins chief baseball officer Derek Falvey wanted him to be Minnesota’s hitting coach. Blue Jays general manager Ross Atkins offered him the role of quality control coach.

Shelton’s wife, Alison, made the most convincing argument to take the job in Toronto.

“When we sat down, she’s like, ‘Do you want to manage?’ I said, ‘Yeah, I think I do,’” Shelton said. “She’s like, ‘If you want to manage, you’ve got to separate yourself from the hitting space and get out of your comfort zone.’ I don’t think, without that push, I would have done it.”

Coming from the forward-thinking Rays organization, he helped the Blue Jays utilize the front office’s scouting reports and analytics and relayed that information to players and coaches in the clubhouse. Essentially, he was charged with helping Toronto get the most out of its players -- something Pittsburgh has struggled to do since its successful run from 2013-15.

“I've just always thought of him as a baseball leader that was very passionate about hitting,” Atkins said. “Derek is very dynamic with players and uses a great wit and his intelligence to connect and relate. He’s going to break down barriers quickly.”

In that role, Shelton was exposed to new ideas and put in a new position. Sharing information with an entire clubhouse of players and staff required trust that could only exist in comfortable, established relationships. Fortunately, that played to Shelton’s strengths.

“He has a way of commanding respect that doesn't require you to keep your head down and stay quiet,” said catcher Luke Maile, who has played for Shelton in Tampa Bay, Toronto and Pittsburgh. “He commands respect because he's a genuinely good dude and he cares. And he cares about each of us, and I think people are starting to understand that.”

Falvey met Shelton in 2007, when he was a first-year baseball operations staffer in Cleveland. They connected over their shared first name while standing around the front office photocopier. A decade later, Falvey asked Atkins for permission to interview Shelton to be Paul Molitor’s bench coach.

“He came in and really impressed everybody,” Falvey said. “I feel like that year for him was incredibly helpful as he prepared for that next role as a bench coach, and that’s ultimately how we ended up down the path with him here.”

The Twins fired Molitor after the 2018 season. Shelton interviewed for the job and emerged as a finalist, having gained the kind of experience teams look for in a modern manager during his year in Toronto and his first season in Minnesota. But the Twins hired Rocco Baldelli, who played for Shelton in Tampa Bay. As happy as the Twins were with their decision, it made for a difficult conversation for Falvey.

“I knew how much he wanted that job and how much he wanted to manage,” Falvey said, “and this was going to be a good opportunity for a lot of reasons.”

Initially frustrated, Shelton thought it over and agreed to return as Baldelli’s bench coach. Driven by the idea that good ideas can come from anywhere, Falvey said he doesn’t care much for titles and hierarchy. So the Baldelli-Shelton relationship, with cooperative leadership coming from a shared office, resembled the collaborative partnership between Falvey and general manager Thad Levine.

The Twins went on to win 101 games and the American League Central crown. Baldelli was named AL Manager of the Year. Shelton became a prime managerial candidate.

“I thought it was only a matter of time,” Falvey said. “I also talked to him about something that was really important, and I believe this: I told him, ‘There’s the next job and there’s the right job.’”

Once again, Shelton had to wait for it.

He nailed his first interview with general manager Neal Huntington, a friend dating back to their time in Cleveland. But Pirates chairman Bob Nutting dismissed Huntington in late October and replaced him with Ben Cherington three weeks later. So Huntington’s managerial search process amounted to laying groundwork.

During the Pirates’ transition, Shelton was wrapped up in the Mets’ search that led them to Carlos Beltrán and eventually Luis Rojas. When that fell through, he awaited the Pirates’ next move.

“It was probably more difficult for my wife and kids because I probably was not a fun person to be around in the gap while they hired Ben,” he said in December. “I will say that I have the cleanest garage of any garage in Florida because I’ve cleaned it about 15 times.”

Shelton interviewed again with Cherington, who hired Shelton on Nov. 27 as the 41st manager in Pirates history.

“When Ben called and wanted to interview him, and I was talking to Ben about it,” Falvey said, “I was like, ‘This is the type of environment that would really suit him.’”

During his introductory press conference, Shelton promised the Pirates would create “a culture where we have fun.” That’s easier said than done, especially this year and particularly with a team that lost 93 games last season. But you won’t hear him complain.

When the Pirates’ first Summer Camp intrasquad game was rained out, Shelton couldn’t help but laugh. Is it this difficult for anyone else in baseball to manage a game?

“His energy, his positivity and his focus on the task at hand, which is to put our players and staff in the best position to succeed, has never wavered,” Cherington said. “His positivity through that, his sense of humor through that, it's been helpful probably for me even at times.”

Hitting coach Rick Eckstein called Shelton “super positive.” Cherington says Shelton quickly learned to delegate and empower others, something Cherington admittedly struggled with during his early days as the GM in Boston. Bench coach Don Kelly says he finds ways to get his point across and get work done while still keeping the mood light and maintaining a good attitude.

Shelton had a text thread and regular Zoom meetings with coaches and staff while the sport was shut down, including one call on March 26: the originally scheduled Opening Day.

“We live in an age where data and analytics and newer approaches to player development and scouting are good. There is, and always will be, a place for experience,” Newman said. “When you’re in a relationship business, like when you’re managing people, the ability to make connections and the ability to help move people in the right direction, in terms of culture and commitment are still critical.”

Shelton’s amiable nature is evident in his dealings with the media, even with press conferences held on Zoom amid the coronavirus pandemic. He’ll point out when one reporter gets a haircut, check in on a TV reporter who’s in post-vacation quarantine and poke fun at a beat writer for making him relive a night his team was on the wrong end of a no-hitter.

He’s even more personable with players behind the scenes. He regularly checked in after Spring Training was suspended, calling to ask about their workouts, wives and kids and what they had going on at home.

Reliever Chris Stratton said Shelton is “just one of the guys” and, with his sarcastic sense of humor, quick to make a joke. Third baseman Colin Moran said the skipper is relaxed and laid-back, but he instills confidence in his players. Catcher John Ryan Murphy praised Shelton’s fierce competitiveness and direct communication.

"I’m glad I’m here with him,” veteran center fielder Jarrod Dyson said. “With Shelton, it's different. I can crack a joke here and there, he’s laughing. Then he’ll crack one on me, and you're laughing. Sometimes the whole team’s laughing because he don’t mind putting me on blast in front of everybody.”

Other traits stand out to players: Shelton’s authenticity, his comfort with being himself and his approachability. Everyone noticed last Sunday afternoon when he ran the bases, with a smile on his face, during rundown drills. He’s directly involved, not looming above the fray.

“There's a respect level of, 'This is your manager, and you're a player,’ but when it comes to communication, you feel like you're on the same level with him,” Opening Day starter Joe Musgrove said. “He'll always let you speak -- not always agree with you, might not always give you what you want. But you're always welcome to come in and talk. He puts the players first.”

To that end, Shelton -- with input from Alison and help from PNC Park operations officials Dennis DePra and Chris Hunter -- completely redesigned the office that belonged to Clint Hurdle the last nine years. They installed a window facing the clubhouse, a reminder of his accessibility to players.

As you walk in, there’s a picture of Jason Grilli and Russell Martin celebrating at Wrigley Field on Sept. 23, 2013, the night the Pirates clinched their return to the postseason after 20 consecutive losing seasons -- “a moment that we have to embrace and I want our players to embrace,” Shelton said.

On one wall, newly painted dark gray, he hung a sign that says “Shooter’s Lounge” in white neon, a gift from a friend who said it had to be in his office if he ever managed in the Majors. He has framed jerseys from Rod Carew and Bill Mazeroski along with a photo of himself, Carew, Mazeroski and Tony Oliva.

There’s a photo of Pittsburgh taken by local photographer Dave DiCello and another of the Roberto Clemente Bridge. There’s the famous picture of Dave Parker, in his “me and the boys boppin’” T-shirt. And there’s a signed photo of former Pirate Bill Robinson, an influential figure in Shelton’s career.

At the end of a detailed, 2-minute, 44-second verbal tour of his new surroundings, Shelton sheepishly apologized for his understandable enthusiasm.

He waited a long time to make that room his own.

“It’s my first manager’s office,” he said, “so I’m pretty excited about it.”