If Not Now, When? Pirates Must Fix Their Biggest Weakness

For the Pittsburgh Pirates' most recent run of playoff success from 2013-15, the formula was simple: get six good innings from the starter and let the bullpen take over.

Opposing teams knew what was coming. Tony Watson in the seventh. Mark Melancon in the eighth. Jason Grilli in the ninth. Game over.

Former general manager Neal Huntington mastered the art of constructing bullpens. In fact, Pirates fans became spoiled. Closers seemed to grow on trees. Somebody always emerged.

That has not been the case under current general manager Ben Cherington.

After trading fan favorite David Bednar, the Pirates turned to Dennis Santana, who dazzled early in the closer role before Gregory Soto took over. Even now, there is little certainty in the ninth inning. And "toss-up" is not just a figure of speech.

Entering the second game of the series against the Athletics in West Sacramento, the Pirates had converted just 15 of their 30 save opportunities. Fifteen wins. Fifteen blown chances.

Another alarming number? Pittsburgh has lost an MLB-high 10 games when scoring six runs or more.

All of it leads to one question: What if?

At 36-37 and nine games behind the first-place Milwaukee Brewers, it is hard for Pirates fans not to wonder where this team would be with merely an average bullpen. After all, this is arguably the best offensive lineup Pittsburgh has fielded since the 2015 season.

If the Pirates are serious about contending, Cherington needs to act quickly.

One intriguing option is a familiar face.

Former Pirates closer Aroldis Chapman re-signed with the Boston Red Sox before the 2026 season, reportedly with the understanding that he would once again play under manager Alex Cora. However, Cora's departure early in the season changed the equation.

Chapman has been dominant, posting a 0.44 ERA and recording 14 saves in Boston's 29 victories. The future Hall of Famer knows Pittsburgh and would instantly provide stability to the back end of the bullpen.

If this team is truly in win-now mode, then now is the time to prove it.

Paul Skenes is pitching like an ace. Brandon Lowe and Ryan O'Hearn have transformed the lineup. Oneil Cruz and Spencer Horwitz are enjoying career years. If not now, when?

Adding Chapman and perhaps another veteran arm, such as left-hander Jalen Beeks, could completely transform the bullpen. What is currently the Pirates' biggest weakness could become a strength with just a couple of moves.

I have spent plenty of time criticizing Cherington in recent columns. After entering the year on one of baseball's hottest seats, he deserves credit for bringing in impact bats and handing out the organization's first multi-year free-agent contract in nearly a decade.

But that alone is not enough.

Build a winner.

Build something that Pittsburgh fans will remember.

Do it, Ben.