Last year, baseball fans watched something very special in the Pittsburgh Pirates. In came Paul Skenes, throwing lightning bolts from the mound with casual ease. His starts turned into must-see events, a rare ray of hope for a passionate fan base. But within the hype for this generation of arms, there was a familiar storm brewing. Questions remain about whether the team surrounding him is being constructed to actually compete, leading to pointed commentary from big-name voices around the league. And one such voice had recently raised the temperature quite a bit.

The Pittsburgh Pirates managed a good win over the New York Yankees recently. They walked it off 5-4 in extra innings on Sunday, April 6th, with Tommy Pham‘s clutch hit providing a bright spot. Andrew Heaney was superb that day, striking out 10 over seven strong innings. But this win feels like a temporary bandage over larger wounds. The team was struggling out of the gate this season, with a disastrous 3-7 record as of April 7. They took some bruising defeats, including a 7-0 shutout by Tampa Bay and a 9-4 loss in their home opener against the Yankees. These early struggles highlight ongoing issues beyond just one exciting win.

Watching the Pirates’ dismantling live, veteran Yankees broadcaster Michael Kay aimed crisp words at the team’s upper management. “We talked about the Pirates not doing much at all during the offseason,” Kay said flatly. He explicitly targeted the team’s front office and owner, Bob Nutting. Kay believes they are failing to put the right talent around their young ace, Paul Skenes, to win. He thinks there’s no passion from the organization with actual investment in return for the fans.

Kay backed up his criticism with a revealing statistic. “The free-agent contracts they signed were all one-year deals to veterans to kind of flush out the roster,” Kay said. He pointed to additions such as Tommy Pham, Andrew Heaney, and Andrew McCutchen. Then the kicker: “The last multi-year free-agent deal they signed was in November of 2016,” for pitcher Ivan Nova. This long gap highlights a trend of avoiding significant, long-term investments in outside talent, fueling frustration about the team’s ambition.

The Pirates’ opportunity: change or miss out?

The Pirates, meanwhile, have made internal investments, maintaining some core players at home. In 2023, they signed outfielder Bryan Reynolds to a big, eight-year extension. Pitcher Mitch Keller signed a five-year deal in 2024, and Ke’Bryan Hayes‘s eight-year deal in 2022. These moves demonstrate a desire to pay their own players. Kay’s point still stands: The team avoids the competitive free-agent market for multi-year deals. That strategy makes building a complete, contending roster around Skenes much harder.

Last season painted this picture clearly. Paul Skenes was untouchable, finishing with an 11-3 record and dazzling 1.96 ERA. He struck out 170 batters and was named the National League Rookie of the Year. Yet, despite this historic performance, the Pirates finished last in their division. They finished the year with a 76-86 losing record. Skenes was an extraordinary solo act, but the team was unable to win consistently around him. This extreme divergence fuels fears about the present and future.

This fear of wasting supreme talent isn’t mere speculation; baseball history has cautionary tales. Look at the Los Angeles Angels for most of Mike Trout’s years, the best player of his generation. They went on to add the two-way superstar Shohei Ohtani. Even with all of those phenomenal players, the Angels rarely sniffed the postseason.

Unfortunately, the Angels aren’t the only team in recent memory to miss such opportunities. The Washington Nationals had a young Juan Soto, a hitting prodigy who led them to a World Series. But the team was unable to maintain success or keep him long-term. The Chicago White Sox also had the exciting Tim Anderson. Despite his talent, the team around him often struggled mightily. The Pirates risk becoming another chapter in this story.

Beyond avoiding major free-agent signings, other key segments of the team are faltering. The Pirates’ offense has struggled in early 2025. Overall, they’re hitting just .197, which is around the bottom of the league (28th). Scoring runs has also been a challenge, placing them 25th overall. Key relievers like Ryan Borucki have struggled in high-leverage situations, an example of inconsistency. It takes more than the brilliance of Paul Skenes to build a winner. And it requires dependable hitting and pitching depth, day after day.

So the question becomes: Do the Pirates’ front office executives change their approach and actually commit to this opportunity window? Or will Paul Skenes’ best years become another painful “what if” story by the Allegheny River?