While there’s plenty of speculation as to what (if anything) the Pittsburgh Pirates will do at the upcoming trade deadline, general manager Ben Cherington is facing the prospect of his best chance yet to snap the postseason drought in Pittsburgh slip through his fingers.

After salvaging the third game of the team’s Yinzerpalooza series at PNC Park, the Pirates are now 54-52 with just one week before the trade deadline. Having constructed one of the best offenses in baseball (save for a few maddening performances here and there), his attention must turn to an abysmal bullpen who threatens night in and night out to hand away the game, and eventually, the season.

Only one other time in his tenure as general manager, which began after the house in the wake of the 2019 season, has Cherington “bought” at the trade deadline. And with the Pirates in the exact same spot they were in two years ago, 54-52 and with a chance at the playoffs, now’s a good time to re-visit the buyer version of Cherington.

Unlike this year’s team, who has pretty clearly defined strengths and weaknesses, the 2024 team needed a little more help in several areas.

Cherington had begun to tinker with the organizational rosters in the days leading up to the deadline, including signing utility minor league-leaguer Jose Rojas to a deal, trading Triple-A outfielder Gilberto Celestino to the Chicago Cubs for cash, and parting ways with lefty Josh Fleming.

But his first major move came on deadline eve, when the Pirates traded lefty prospect Luis Peralta to Colorado in exchange for major-league left-hander Jalen Beeks.

At the time of the trade, Peralta was a high-rising prospect who had started the season in High-A, but was quickly rocketing through the minor league circuit. But he was the price required to bolster the Pirate bullpen and give them an established lefty who had put up a 4.74 ERA and 1.358 WHIP through 49.1 innings in Colorado.

Cherington was hoping that, rather than promote an unknown arm (whether it was Peralta or someone else), having someone there who had been there and done that would help secure the back end. It didn’t really work.

In 20.2 innings for the Pirates, Beeks posted an average 3.92 ERA, but a dangerously high 1.790 WHIP and a low 1.89 strikeout-to-walk ratio. He wasn’t awful, but he also wasn’t the shutdown arm the Pirates envisioned him as. Some of his struggles were only amplified as Peralta made his major league debut for the Rockies late in the season, and allowed just one run during his first 12.1 innings in the bigs.

It should be noted that Peralta’s early success hasn’t lasted. The following season, Peralta posted a 9.47 ERA, 2.316 WHIP, and 0.89 strikeout-to-walk ratio in 19 innings. Now 25, he has spent this season in Triple-A. But the Beeks deal was as good as it got for Cherington.

During his rather muted spending spree, the general manager swung two trades on deadline day to address the batting department.

In from Toronto was infielder Isiah Kiner-Falefa, who was acquired at the cost of power-hitting prospect Charles McAdoo. At the time, McAdoo was recently promoted to Double-A Altoona and was slugging .490 with the Curve as a 22-year-old. But for Cherington, it was worth it to bring in Kiner-Falefa, who was on track for a career year after slashing .292/.338/.420 (.758 OPS) with the Blue Jays.

Upon arrival in Pittsburgh, the Pirates stripped him of his position flexibility and hoped that his Gold Glove résumé as a third baseman in 2020 would translate to a role at shortstop.

Unfortunately for the Pirates, Kiner-Falefa’s defense was largely average at best. Much worse, his bat had plummeted down to a .240 average, and he finished the season with a .587 OPS for the Pirates. Just for reference, Pirate batters with higher OPS figures included Jack Suwinski, Edward Olivares, and Yasmani Grandal.

It was a swing and a miss, but far from the disaster that Cherington’s acquisition from Miami was. That same day, the Pirates traded minor-league infielder Garret Forrester and righty relief prospect Jun-Seok Shim to the Marlins in exchange for outfielder Bryan De La Cruz.

Unlike McAdoo, neither Forrester nor Shim have played major league games (although the former has gotten some Triple-A time this season), but De La Cruz performed so abysmally the trade might be a loss even if neither prospect ever pans out.

The Pirates knew at the time that De La Cruz was a liability in the outfield, but Cherington hoped that the batter who slashed .245/.289/.417 (.707 OPS) with 18 home runs in just over 100 games could make up for his errors with the pop in his bat.

He was wrong. Falling even harder off the cliff than Kiner-Falefa did, De La Cruz slashed .200/.220/.294 (.514 OPS) in 44 games. Even worse, De La Druz was indeed the nightmare defensively that fans feared. By season’s end, he finished with -7 defensive runs saved and -8 outs above average, per Baseball Savant, both among the worst in baseball.

Smaller moves made by Cherington included trading starter Quinn Priester to Boston for utility fielder Nick Yorke, and sending righty Patrick Reilly to Baltimore for another utility man in Billy Cook. Both of those players got runs at the end of the 2024 season, and ironically, are the only two of this five-player group to still be with the organization.

As soon as the trio of Beeks, Kiner-Falefa, and De La Cruz arrived in Pittsburgh, the season cratered. Starting on August 4th, the Pirates lost ten games in a row, plummeting them back below .500 and wiping out any chance at the playoffs.

Those none of the acquired players did much to help down the stretch, it probably didn’t matter all that much. That losing streak had cost them everything.

Now, two years later and in the third year of the Paul Skenes era, the Pirates desperately hope not to have a repeat of that season. We don’t have a ton of history to go off of when judging how Cherington handles a trade deadline in Pittsburgh as a buyer.

What we do have, however, is rather uninspiring. None of these players are still a member of the Pirates less than two years later, despite only one them acquired as a pure rental.

Cherington also does not have any assets or success to show for these purchases. His team cratered immediately, and by season’s end Beeks had walked and De La Cruz was left unsigned. Kiner-Falefa, the only player to start the next season with the Pirates, was cut late in the year, though Cherington opted not to trade Kiner-Falefa and instead waived him at the end of August.

So, here’s the general manager’s big chance to help change the narrative not just around him, but how around his team is constructed and whether they can go the distance in August, September, and October.