Pittsburgh Pirates manager Derek Shelton is failing his first big test

The Pittsburgh Pirates made some big changes after the 2019 season. One of those overhauls involved letting go of long-time manager Clint Hurdle and bringing in Derek Shelton. Shelton had long been a coach, working as a hitting coach for the Cleveland Indians from 2005 through 2009, then joining the Tampa Bay Rays’ coaching staff in the same role from 2006 through 2016. He was then a quality control coach with the Toronto Blue Jays in 2017 before he was hired as the Minnesota Twins’ bench coach from 2018 to 2019.

Shelton was brought in at a difficult time. The Pirates were just starting their rebuild, and rebuilding the coaching staff was one of the many things they had to take care of early. Based on the team's timeline and ascent, 2024 represents the first big test of Shelton’s career as a MLB manager, where his on-field performance should hold actual stakes. The Pirates are finally starting to look like a potentially competitive team, but Shelton is failing. 

This past homestand may have been the biggest one in the Pirates’ recent history. The Pirates were heading into two series against the Arizona Diamondbacks and San Diego Padres, two teams barely ahead of Pittsburgh in the Wild Card standings. What could have been a season-defining six games ended up being one of the most heartbreaking weeks of recent Pirates history.

The Pirates went 1-5, and a lot of the blame can be pinned to Shelton. The management of the bullpen during this homestand was horrendous. For example, in Game 1 of the series, the Pirates entered the eighth inning tied up at 8-8. Shelton turned to the struggling Colin Holderman. Holderman had nearly blown one of the games in Arizona the previous week, and blew the previous game against the Houston Astros. But instead of giving Holderman a breather, the Pirates opted to use him in a close game, and Holderman promptly let the D-Backs take the lead.

Derek Shelton helped bungle massive homestand for Pirates

Although Dennis Santana allowing a home run would be the nail in the coffin, the question still remains why Shelton would turn to a clearly gassed Holderman in this situation? That same question came up again in the final game of the series. The Pirates went into the top of the seventh with a 4-2 lead. Once again, Shelton turned to Holderman. 

Holderman allowed two base runners to reach, but recorded two outs, with Joc Pederson, a known right-handed killer, looming. With left-handed reliever Jalen Beeks warming up and the three-batter minimum already accounted for, the Pirates opted to keep Holderman in for another batter. He promptly allowed a three-run home run, which almost wasn’t enough for the D-Backs to hold onto for the series win. That’s because the Pirates were on the verge of rallying back.

The Pirates led off the bottom of the ninth with a walk and single. In came Isiah Kiner-Falefa, one of the team’s acquisitions intended to improve the offense. Instead of having the guy who was batting around .290 and had both a double and triple earlier in the day swing the bat, Shelton opted to have IKF bunt. He wasn’t able to get the bunt down and popped out. The Pirates fell one run shy of at least tying the game.

Then the Padres came to town. After dropping the first game of the series, the Pirates were in a great position to win Game 2. Heading into the ninth inning, the Pirates had a one-run lead. In came David Bednar to try and close things out, but he allowed a home run to Jackson Merrill to tie the game up. Although the Pirates loaded the bases in the bottom of the inning with only one out, they did not score.

That offensive deficiency paved the way for Shelton to make two managerial blunders in one inning. Shelton, against all logic and reason, turned to Colin Holderman once again. On cue, he allowed three runs to score. Now sure, Yasmani Grandal didn’t do Holderman any favors, and only one of the runs was earned, but why, after blowing his last three games, would you turn to Holderman again?

The Pirates came very close to winning this game as well. They scored two in the bottom of the tenth inning. With two in scoring position and two outs, Grandal came to the dish. Grandal has struggled most of the year, and with the game on the line, the Pirates certainly had options. They had Bryan De La Cruz, another trade acquisition they hoped would help improve the offense. But, more importantly, they had Joey Bart on the bench.

Bart has destroyed left-handed pitching this year, and with lefty Adrian Morejon in, you would think the Pirates would turn to their hottest hitter. Instead, the Pirates stuck with Grandal, who promptly grounded out, ending what was a once-promising game.

But the reasoning behind why he left Grandal in to hit might be worse than the decision itself. According to Shelton, he let Grandal hit because he’s had some good ABs over the last month -- and plus, Bart is 0-for-3 against Morejon throughout his career. Not only is three at-bats way too small of a sample size to avoid Bart there, this is also a different Bart and a different Morejon than we’ve seen in the past. At the time of writing this, Bart has the highest OPS of any catcher with at least 150 plate appearances this season, and Morejon has a 1.90 ERA, 2.87 FIP, and 1.25 WHIP. Both are in the midst of breakout seasons.

Shelton is right. Grandal has been putting together better ABs recently. He is batting .316 with a 1.014 OPS over his last seven games. But do you know who's been just as good? Joey Bart, who entered the day batting .346 with a .994 OPS over his past seven games. On top of that, Bart had been putting together better ABs all year, while Grandal hasn't, and Bart was batting over .400 with an OPS over 1.100 against lefties.

The final game of this homestand was yet another nightmare. The Pirates went into the top of the ninth with a one-run lead. In came David Bednar, who allowed one earned run in each of his last three outings. The Renegade has certainly not been his normal self this year, and he allowed three earned runs in this difficult-to-swallow contest. Some scored after the Pirates put in Kyle Nicolas, who, despite being one of the Pirates’ hottest relievers, was only used three times this homestand. The Pirates once again tried to rally back, but came just one run short.

Throughout this homestand, the Pirates had the lead or were tied heading into the seventh inning or later in five of the six games. In four of those games, the Pirates would go on to score at least one more run following that line of demarcation, scoring a total of seven runs in the seventh or later during the six games. The fact they came away with one win despite all of that is a sad sight for Pirates fans.

If the Pirates take two of three from both the D-Backs and Padres (possibly even a sweep of the D-Backs), something that was very doable, and something the team gave Derek Shelton a very good chance at doing, they would have slingshotted themselves into a very good spot. Instead, they’re once again on the backfoot and will have to claw themselves back into contention.

It's impossible to expect any manager to be perfect, and it’s hard to manage around two of your best relievers imploding at the same time. But this isn’t 2021 or 2022 anymore, when Shelton's best late-game options were Anthony Banda, Chris Stratton, or Chase DeJong. Shelton has options. The Pirates are a good team with a ton of potential, but bad decisions by Shelton have held back a lot of that potential. He could have given Holderman or Bednar a breather and given Kyle Nicolas or Dennis Santana a crack at a hold or save opportunity. He could have pinch hit for Grandal by turning to one of the right-handed bats Ben Cherington brought in. He could have let Isiah Kiner-Falefa swing the bat when he's been red hot lately. 

In the end, bad decisions on the part of Derek Shelton during this most recent homestand might end up costing the Pirates gravely. Ultimatley, these decisions could cost the Pirates a chance at the Postseason this year. These are the kind of games fans are going to look back at and think “what if” if the Pirates end up failing to reach October by a few games, which looks very possible. This season, and especially this homestand, was Shelton’s first big crack as an MLB manager to lead a team to the Postseason. Right now, he is failing to do so. His days as the Pirates’ manager might be numbered if things don’t start turning around, and especially if he doesn’t start pushing the right buttons.