Demilio: Pirates Need to Show Post-Holiday Aggressiveness

Christmas has come and gone. For me, that serves as unofficial halftime of the Major League Baseball offseason.

There tends to be a rush of free agent signings and trades before the brief hiatus to celebrate the holidays. After a couple days off, activity begins to pick up again as we get set to welcome in the new year.

By this logic, the Pittsburgh Pirates had a relatively quiet first half of the offseason. The first move the Pirates made was adding some bullpen depth by acquiring Peter Strzelecki from the Cleveland Guardians for cash. The right-hander will likely be battling for a spot in the bullpen this spring.

The Pirates again looked to the Guardians to fill their need at first base. Earlier this month, Pittsburgh acquired Spencer Horwitz from Cleveland after he was dealt by the Toronto Blue Jays earlier in the day. Though he’s struggled in his career against lefties, Horwitz should give the Pirates a primary first baseman in a platoon against right-handed pitching.

A couple days later, the Pirates swung a trade with the Boston Red Sox, landing infielder Enmanuel Valdez for a pitching prospect. Valdez might not crack the Opening Day roster but provides some depth.

Then of course, on the eve of Christmas Eve, the Pirates brought back Andrew McCutchen for another season. At 38 years old, he may not be the player he once was, but McCutchen still provides some value as a designated hitter.

Even with the flurry of activity, the Pirates need to get more aggressive during the second act of the winter and build a playoff-caliber team between now and the start of spring training.

The Pirates still have a lot of work to do and general manager Ben Cherington is undoubtedly on the phone with free agents and other general managers in search of roster upgrades.

But Cherington is behind the eight ball. As redundant as it is to say, the Pirates will not be shopping at the top of the market. Sluggers such as Anthony Santander and Teoscar Hernández and left-handed relief ace Tanner Scott are perfect fits on paper but will not be playing in Pittsburgh next season — barring the biggest of surprises.

But there are other ways for the Pirates to try and build a competent team in hopes of reaching the postseason for the first time since 2015.

There won’t be any nine-figure contracts handed out to a free agent. The Pirates won’t part with a prospect like Bubba Chandler to add an impact bat to the lineup, which is understandable.

But in order to get Horwitz, Cherington shipped out at least a fairly-significant package to the likes he really hadn’t done since taking over the Pittsburgh Pirates’ front office.

It’s a promising development, but the Pirates need to be willing to part with some more young talent in order to help the big-league club. And no, I’m not talking about someone from the MLB roster like Jared Jones.

But Cherington, despite financial restraints from ownership, has to be willing to show more aggressiveness in free agency. Under his watch, the Pirates have yet to give a free agent a multi-year contract. This is his fifth offseason. The Pirates are no longer rebuilding, so that needs to change.

The Pirates need to add at least one more bat, preferably an outfielder. They also need to acquire a left-handed reliever and another arm to sure up their bullpen. If I was in Cherington’s shoes, I’d also think hard about adding an everyday shortstop and a veteran starting pitcher to provide more depth to the rotation.

Despite a last place finish in 2024, the Pirates window to compete is open. I’ve said it before and I’ll say it again — it will remain open as long as Paul Skenes is in a Pittsburgh Pirates’ uniform. Given the microscopic salary he will command compared to his talent, now is the time to actually spend before he sees significant raises through arbitration.