Pirates fans jealous of White Sox for first time ever after latest bombshell

As Pittsburgh Pirates fans are forced to endure yet another season of losing baseball under penny-pinching owner Bob Nutting, one look at the moves happening on the South Side of Chicago is enough to make them turn green with envy.

Jerry Reinsdorf, principal owner of the Chicago White Sox, announced Thursday that he has reached a long-term investment agreement with billionaire investor Justin Ishbia to potentially sell his majority stake in the club in five years' time.

According to the press release, the agreement gives Reinsdorf the "option" to sell his controlling stake to Ishbia between 2029 and 2033. Ishbia currently holds a minority stake in the team.

No transaction will take place before 2029, but this agreement allows Ishbia to potentially obtain controlling interest in the team. Given that Reinsdorf is currently 89 years old, the agreement could presumably go into effect sooner rather than later.

The White Sox have struggled mightily under Reinsdorf's leadership over the past several years. Since winning the World Series in 2005, Chicago has made the playoffs just three times and has had only five winning seasons in that 20-year span. Last season, the White Sox set a new MLB record – and not the good kind – with 121 losses.

As Pirates fans began to learn of Reinsdorf's agreement to sell, one by one, they all began to ask the same question: Will Nutting be next?

Pirates fans jealous of White Sox for first time ever after latest ownership bombshell. Will Bob Nutting be next?

When you look at the Pirates over nearly the last two decades under Nutting's ownership, they look alarmingly similar to the White Sox under Reinsdorf (except the latter franchise actually has a World Series title in this century). The Pirates have finished with a winning record in just four of the 18 seasons that Nutting has owned the team, with their last winning season coming in 2018.

The Pirates went 76-86 in 2024 en route to their fourth last-place finish in the past six seasons. They haven't reached the postseason since 2015 and have just three postseason appearances since 1992. With a 23-39 record so far in 2025, Pittsburgh currently occupies the basement of the National League Central division and appears destined to stay there as long as Nutting is in charge.

Reinsdorf has been owner of the White Sox for nearly four decades, and the franchise at least had some good years under his leadership before things began to go south and he agreed to a potential sale. Pirates fans are hoping they won't have to wait another 40 years for Nutting to do the same.

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