Ben Cherington might have made the best trade of his tenure as Pittsburgh Pirates general manager last offseason. The problem? The Pirates might only get one season out of its biggest prize.
Brandon Lowe's selection as a Louisville Slugger Silver Slugger Award finalist at second base is the latest validation of what was an overwhelmingly successful first season in Pittsburgh. Lowe joins Milwaukee Brewers second baseman Brice Turang as the two finalists for the award after hitting .260 with 35 home runs, 96 RBI and an .824 OPS in 2026.
But while the recognition reinforces just how much value Cherington acquired in last December's three-team trade with the Tampa Bay Rays and Houston Astros, it also highlights an uncomfortable reality. The Pirates finally acquired the kind of impact hitter their lineup desperately needed, only to potentially lose him before they could build a legitimate contender around him.
And that would make one of Cherington's greatest accomplishments feel like an enormous missed opportunity.
We present to you: all 35 of Brandon Lowe's home runs from this season. 💣 pic.twitter.com/QO8zCc0MPK
— Pittsburgh Pirates (@Pirates) November 5, 2026
Brandon Lowe trade could become defining missed opportunity of Ben Cherington's Pirates tenure
When Pittsburgh acquired Lowe alongside Jake Mangum and Mason Montgomery in exchange for sending Mike Burrows to Houston, the move represented an unusually aggressive approach from a front office frequently criticized for its reluctance to sacrifice pitching depth for established offensive production.
The gamble paid off almost immediately. Lowe provided the middle-of-the-order power the Pirates had been missing for years, helping transform an offense that finished last in baseball in 2025 into a considerably more dangerous group. His 35 home runs led Pittsburgh, while his 5.4 bWAR represented the highest single-season total by a Pirates position player since Bryan Reynolds in 2021.
Lowe's contributions extended beyond his bat, too. He also became a Gold Glove finalist after a remarkable defensive turnaround at second base. After recording minus-14 Defensive Runs Saved with Tampa Bay in 2025, he finished his first season in Pittsburgh with 13 DRS and 15 Outs Above Average.
Cherington acquired a player who performed like one of baseball's premier second basemen. That should be an unequivocal success story. Instead, the Pirates are facing the very real possibility that Lowe's first season in Pittsburgh will also be his last.
The organization extended Lowe a $23.15 million qualifying offer earlier this week, but he's widely expected to decline it in pursuit of a multiyear contract. Pittsburgh would receive draft-pick compensation if he signs elsewhere, but that wouldn't come close to replacing his production in the immediate future.
That's where the flaw in Cherington's otherwise brilliant acquisition becomes impossible to ignore. What good is finding the missing piece if the organization isn't prepared to keep it?
The Pirates deserve credit for making the trade regardless of Lowe's ultimate decision. Mangum and Montgomery remain valuable pieces of the roster, and getting a season of elite production from Lowe for an $11.5 million salary was an excellent return on the investment. But the circumstances surrounding his potential departure expose a much larger organizational problem.
The Pirates spent years trying to develop enough offensive talent to complement their promising young pitching staff. When Cherington finally acquired an established difference-maker, Pittsburgh improved to 82-80 to secure its first winning season since 2018.
That should have established a foundation for something bigger. Instead, the organization could enter 2027 needing to replace the player most responsible for its offensive improvement. And given Pittsburgh's history of avoiding expensive multiyear commitments, there's little reason to assume the Pirates will successfully replace Lowe's production on the open market.
The most frustrating part is that this outcome was entirely foreseeable. Lowe arrived in Pittsburgh with just one season remaining on his contract. If he performed poorly, the Pirates could simply move on. But if he delivered exactly what they hoped, retaining him would become considerably more expensive.
Cherington deserves credit for identifying an opportunity and capitalizing on it. But a successful trade doesn't automatically translate into successful roster construction, particularly when the acquired player becomes too expensive for the organization to retain.
Lowe's Silver Slugger recognition should be another reason for Pirates fans to celebrate one of Cherington's smartest moves. Instead, it's becoming another reminder of how quickly Pittsburgh's financial limitations can undermine its baseball decisions.
The Pirates found their impact bat and proved what their lineup could accomplish with him. Now they have to decide whether they're actually willing to pay to keep that success going.
Otherwise, Cherington's best trade might ultimately be remembered as one of the biggest missed opportunities of his tenure.
