That Didn’t Work: Revisiting All 7 Pirates Trade Deadline Deals

Optimism was high for the Pittsburgh Pirates after they were trade deadline buyers for the first time under Ben Cherington’s watch.

The Pirates were tied for second place in the National League Central at the deadline and were only two games out of a wild card spot, hoping to see the postseason for the first time since 2015.

Instead of gaining ground in the race, the Pirates quickly fell out of contention due to a horrid stretch of play in August that included a 10-game losing streak. Now with three games left on the calendar, the Pirates (74-85) need to sweep their series against the New York Yankees to finish with a better record than last year.

Cherington and the Pirates were active at the deadline with seven trades executed within roughly 24 hours of the deadline. However, the deadline as a whole for the Pirates did not go anywhere near according to plan.

Pirates trade LHP Martín Pérez to the Padres for LHP Ronaldys Jimenez

The lone “sell move” the Pirates made turned out to be a costly one. Pérez’s absence was felt after fellow left-hander Marco Gonzales was sidelined for the year in early August. The Pirates had to mix and match to fill his rotation spot with options such as Jake Woodford and bullpen games.

Pérez, meanwhile, has been great with the playoff-bound Padres. In nine starts since the trade, the left-hander is a spotless 3-0 with a 2.61 ERA.

Jimenez totaled four starts with the DSL Pirates post-trade. He posted a 4.91 ERA and struggled with command, issuing 12 walks and striking out 11 in 7.1 innings.

This looks like one the Pirates wish they didn’t make, even though dumping salary was needed to make other moves.

LHP Josh Walker acquired from Mets for LHP Nicolas Carreno

The Pirates added to their left-handed bullpen depth by adding Walker, who had been designated for assignment by the Mets earlier in the week. Walker never made it up to the Pirates after being designated for assignment a short time later. He remained in the organization on a minor-league deal signed later in August.

Carreno made three starts in the DSL for the Mets after the trade. He went 0-1 with a 3.48 ERA.

INF/OF Nick Yorke acquired from Red Sox for RHP Quinn Priester

Pittsburgh and Boston swapped former first-round picks. Yorke tore up the Triple-A competition and recently made his MLB debut. In eight games since being called up, Yorke has hit .259 with a .670 OPS, one home run, three RBIs and two steals.

Priester has yet to pitch in the big leagues for Boston and struggled with Triple-A Worcester. In nine starts, the right-hander owned a 5.40 ERA.

Given the Pirates’ need for position-player help, this one still seems like a good trade.

INF/OF Billy Cook acquired from Orioles for RHP Patrick Reilly

The Pirates made a similar deal with another team in the American League East in Baltimore. The Bucs dealt from their glut of pitching prospects to once again add a bat and landed on Cook.

Like Yorke, Cook performed at a high level with Indianapolis and was called up by the Pirates in September. The 25-year-old hasn’t done much at the plate with a .211/.211/.395 slash but has already been responsible for six defensive runs saved in 10 games in the outfield.

Reilly, the Pirates’ fifth-round pick in 2023, went 1-1 with a 3.73 and 38 strikeouts in 31.1 innings across eight appearances/six starts with Double-A Bowie.

Given each organization’s need and the upside of both players, this feels like a win-win for now.

LHP Jalen Beeks acquired from the Rockies for LHP Luis Peralta

The lone rental the Pirates added at this year’s deadline was Beeks. The left-hander has pitched pretty well since he was added. In 25 relief appearances, Beeks is 1-0 with a 3.98 ERA and recorded one save. But the price to land him could be costly.

The Rockies expedited Peralta to the big leagues after a terrific minor-league season between both organizations. In 13 appearances since he was called up to the majors, Peralta has yet to allow a run and has 11 strikeouts in 10.1 innings.

While Beeks has been solid, he’ll hit free agency this offseason. The Rockies will have the 23-year-old Peralta for years to come, and if he keeps pitching like this, will be a big piece in their bullpen.

INF/OF Isiah Kiner-Falefa acquired from Blue Jays for INF/OF Charles McAdoo

The Pirates gambled in trading one of their top performing position player prospects for Kiner-Falefa, who was on the injured list at the time of the deal.

Prior to getting hurt with Toronto, Kiner-Falefa was performing well at the plate, but he hasn’t had the same success with the Pirates despite a respectable .251 batting average. But he has provided quality defense at both middle infield spots and third base.

McAdoo also regressed offensively after the trade. He hit just .186 with a .609 OPS with Toronto’s Double-A club.

The Pirates have Kiner-Falefa under club control through next season. His defense is solid and his versatility might be his best attribute. He’s a good clubhouse presence, too. The only box left to check is better offense.

OF Bryan De La Cruz acquired from Marlins for RHP Jun-Seok Shim and INF Garret Forrester

And here’s the big one. The Pirates, unfairly, were expecting De La Cruz to anchor the middle of the lineup. Despite hitting 18 home runs with the Marlins to begin the year De La Cruz had a lowly .289 OBP and an unspectacular 90 wRC+ along with questionable defense.

But De La Cruz’s time with the Pirates had been disastrous. Through 43 games in the black and gold, he’s slashing .204/.220/.299 with nine extra-base hits including only three home runs, the latest of which came in Thursday’s loss to the Brewers. He’s struck out 50 against three walks in 164 plate appearances.

Part of De La Cruz’s appeal was his contractual control. This offseason would be his first time being arbitration-eligible. But that likely won’t even matter as he’s become a clear non-tender candidate this offseason.