Pirates’ Slim Playoff Hopes Take Massive Hit On Monday Night

Pirates Don Kelly
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CHICAGO, ILLINOIS - APRIL 10: Manager Don Kelly #12 of the Pittsburgh Pirates looks on against the Chicago Cubs during the sixth inning at Wrigley Field on April 10, 2026 in Chicago, Illinois. (Photo by Michael Reaves/Getty Images)

The Pittsburgh Pirates were aggressive — by their standards — in the offseason. Free-agent contracts were signed, trades were executed, and Don Kelly was set to start his professional managerial career off on the right foot. Everything seemed to be going accordingly to plan until August. A 12-15 record in the final full month of summer hurt. Now, the group is hanging on by a thread with the NL playoff picture taking shape. It would truly be a miracle if the organization slipped into the postseason. It doesn’t help that the Arizona Diamondbacks and San Diego Padres are standing in the way, either.

The Pirates were off on Monday and started the day 6.5 games out of the final Wild Card spot. With only 12 matchups left on the schedule, it almost feels liking winning out is necessary. That reality became even more evident after the Diamondbacks and Padres played.

San Diego, which now leads Arizona by 2.5 games — and Pittsburgh by 7, escaped with an 8-7 victory over the Colorado Rockies.

The Miami Marlins had the Diamondbacks under control until a fierce comeback occurred. Arizona ended up scoring four runs in the final two innings to claim victory, also by a score of 8-7.

With every game mattering, being six games back instead of seven could have made a difference for the Pirates. It is unlikely that the team will find a way to go 12-0, or anything close to that, but there was hope.

What fans were rooting for on Monday evening went in the complete opposite direction. On top of that, the Padres and Diamondbacks play one another in the final series of the season. One of the teams has to win at least two of those games.

Pirates Set To Fall Short Of Postseason For 11th Straight Season

Pittsburgh had a great stretch from 2013-15, but the franchise has come back down to earth since. This season has been the closest to playoff relevancy for the first time in over a decade. Unfortunately, a pair of teams out West are taking October baseball away from the Buccos. Never say never, but it sure feels like any hope would be irresponsible at this point.

Kelly will plan to enter an offseason that will have plenty of uncertainty. There could be a lockout due to the ongoing Collective Bargaining Agreement negotiations, so a lot of planning will revolve around that.

Pittsburgh Has A Big Decision To Make In The Coming Weeks

Ben Cherington was hired to be the Pirates’ general manager back in 2019. More has gone wrong than right since that move. Despite this, Pittsburgh is right on the bubble of having a winning season. The goal should be to accomplish more than that, but it could save the executive at the end of the day.

Chairman and Owner Bob Nutting needs to quickly make a decision on Cherington and if he should still be the guy in charge of personnel movements. If someone were to ask the average fan, the response would overwhelmingly be that a change of course is needed. A playoff appearance could have kept his seat lukewarm, but now it might be getting extremely hot.

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Pirates’ Slim Playoff Hopes Take Massive Hit On Monday Night

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