Pirates
Demilio: Nutting, Pirates Need to Take Advantage of Window Starting This Winter

You can feel the frustration growing even more than usual among fans of the Pittsburgh Pirates.
They certainly aren’t at fault. Even the most loyal fans can only take so much losing, and the better part of the last three decades would strain even the biggest of diehards.
The Pirates’ 76-86 showing this season did nothing to change the perception. It marked the identical record the team had in 2023, only this time, came with another last place finish.
Despite the same win total as the year prior, the team’s window to compete is open, and it’s primarily because of one man.
Paul Skenes wrapped up his first season in the big leagues and was every bit as advertised — and then some. The big right-hander came out of the gate firing and started for the National League in the All-Star Game.
He finished his stellar rookie campaign at 11-3 with a sparkling 1.96 ERA. Skenes also set the Pirates’ rookie single-season strikeout record with 170, all while featuring impressive control and holding opponents to a .198 batting average.
Skenes is part of a two-horse race to take home Rookie of the Year honors with San Diego Padres center fielder Jackson Merrill also in contention. A case could be made for either player. I’d still give the edge to Skenes.
Regardless of whether he wins or not, Skenes will get a full year of service time by placing in the top two. Because of that, Skenes will be eligible for free agency following the 2029 season as opposed to 2030.
The Pirates’ theoretical window will remain open as long as Skenes is in a black and gold uniform, but getting to free agency a year earlier that normally means the window won’t remain open as long as it could have.
Unless, of course, owner Bob Nutting gives Skenes a check to extend his team control further into his career. It would take a guarantee larger than any other contract in team history, a figure that would far eclipse Bryan Reynolds $106.75Â million extension from 2023.
But regardless of whether or not the Pirates’ extend Skenes, they need to do everything they can to go for their first World Series since 1979 while they still have him atop their rotation.
It’s going to take Nutting allowing general manager Ben Cherington to increase the payroll significantly, well more than what we’ve been accustomed to seeing — though that’s not a high bar to clear.
But the Pirates, despite Skenes and a strong starting rotation, aren’t necessarily close to the playoff picture. Only three teams in the National League finished with a worse record than the Pirates in 2024; the Colorado Rockies, Miami Marlins and Washington Nationals.
In order to get into the top six of the league — whether by winning the division or securing one of the three Wild Card spots — the Pirates will need to make impactful additions this offseason and spend wisely.
The holes on the roster are clear. The Pirates need to boost an underwhelming lineup. They need at least two bats — one at first base and one in the outfield — to help lengthen their lineup. The bullpen, which was a major disappointment this season, is also in need of a facelift.
The offseason won’t officially begin until free agency opens five days after either the New York Yankees or Los Angeles Dodgers win the 2024 World Series. When it does, the Pirates need to look to shop in a different aisle than the ones they usually browse this time of year.
Skenes is quite simply too good to stick to the status quo. He gives the Pirates an advantage they haven’t had in forever.
It’s on Cherington to find the right players to build the Pirates into a winner. It’s on Nutting to allow that to happen, and it needs to start happening now.