Jun 5, 2024; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates general manager Ben Cherington speaks on the phone in the dugout. Charles LeClaire-Imagn Images

Yankees Broadcaster Blasts Pirates Leadership for Embarrassing Offseason

Originally posted on New York Yankees on SI
By Tyler Maher | Last updated Apr 7, 2025 8:00 AM ET

New York Yankees fans love to criticize Hal Steinbrenner and Brian Cashman for not spending more and doing more to help their team win. The Yankees haven't won the World Series since 2009, which feels like a lifetime for some of their supporters.

However, things could be much worse. Just ask Pittsburgh Pirates fans.

The Pirates haven't won a World Series since 1979, nor have they come particularly close. They've been largely inept over the last 45 years, making just six playoff appearances during that time.

The last decade has been especially rough for Pittsburgh. The franchise has endured nine straight losing season since its last postseason appearance in 2015, and seems well on its way to another moribund campaign after starting the year 3-7.

New York, on the other hand, hasn't had a losing season since 1992 and makes the playoffs almost every year.

While the Yankees are always near the top of the league in payroll, the Pirates usually rank near the bottom. According to Spotrac, New York has the third-highest payroll in baseball at $289 million — over $200 higher than Pittsburgh's $88 million figure (26th in MLB).

The Pirates have kept their payroll low by limiting their free-agent spending, which Yankees TV broadcaster Michael Kay called out on air during Sunday's game.

Yankees broadcaster Michael Kay talks about the state of the Pirates and the potential they could have but don’t have. Take a watch. pic.twitter.com/aLIKhG7LsB
— Greg Finley (@_GregFinley) April 6, 2025

Kay noted that Pittsburgh only signed one-year deals in free agency last winter, which has been the organization's strategy for years. According to Kay's research, the Pirates haven't signed a free agent to a multi-year deal since December 2016, when they inked former starting pitcher Ivan Nova to a modest three-year, $26 million contract.

While Pittsburgh's lack of spending could be justified during its recent rebuild, that's no longer the case. The franchise has a generational talent in Paul Skenes, but still failed to build a competitive team around him last winter.

If owner Bob Nutting doesn't start investing more in the roster and allow general manager Ben Cherington to spend more aggressively, the Pirates risk squandering Skenes' prime, similar to how the Los Angeles Angels wasted some of the best years of Mike Trout and Shohei Ohtani's careers.

Skenes is arguably the best pitcher in baseball, but he only plays every fifth day. Pittsburgh needs to give him a strong supporting cast if it wants to be a playoff contender.

The Pirates have a beautiful ballpark, a passionate fanbase and a bona fide ace. Now they just need an owner who cares.

This article first appeared on New York Yankees on SI and was syndicated with permission.

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