José Caballero and 3 more trade deadline steals that look like genius in hindsight

Third-year shortstop José Caballero can officially say he’s the reason that the New York Yankees reached the 2025 MLB postseason.

Less than two months after the Yankees acquired him from the Tampa Bay Rays, Caballero clinched the Yankees’ latest postseason berth with a two-out, walk-off single against the Chicago White Sox earlier this week. 

“I go out there and try to win,” Caballero said in a jubilant Yankees’ clubhouse, “and I don’t pay attention to anything else.”

The Yankees landed Caballero in a trade involving outfield prospect Everson Pereira and a player to be named later. It may not have been the flashiest move, especially during a deadline when the Yankees added All-Star relievers David Bednar and Camilo Doval, but we’re sure that Yankees general manager Brian Cashman has no regrets.

Caballero is one of several players leaguewide involved in July trades that likely went under the radar. All of those players are either on playoff-bound teams or organizations that are still in the postseason mix with four days left.

José Caballero, SS, New York Yankees

Caballero may have exceeded whatever expectations the Yankees had when they snagged him from the Rays. Not only does he have an above-average .666 OPPS, but his 14 steals in 17 attempts have been a massive boost to a Yankees team with, shall we say, severe baserunning issues.

By no means will we go so far as to suggest Caballero is the Yankees’ long-term shortstop answer. His 19.3% strikeout rate and 13.6% walk rate are considerably better than his respective 26.3% and 8.9% averages, though Caballero is also only in his third seasons. However, he also just turned 29 in August, so it’s not unfair to predict that his 2026 numbers will be more in line with his production in Tampa Bay.

Regardless, Caballero is a pivotal reason why the Yankees still have an opportunity to win the AL East for the third time in four years. That alone warrants him a spot on this list. 

Ramón Laureano, LF, San Diego Padres

Unfortunately for the Padres, they’ll be without Laureano through at least the NL Wild Card Round. The veteran left fielder fractured his right index finger against the Milwaukee Brewers earlier this week, a crushing blow to a Padres team seeking its first NL East title since 2006. 

“He’s a winning player,” Padres manager Mike Shildt said after the injury. “It hurts. But we’ve got to figure out a way to move forward, which we will.”

Shildt did not commit to Laureano potentially returning for the NLDS if the Padres advance that far. San Diego entered Thursday as the NL’s No. 5 seed, setting them up for a Wild Card Round date with the Chicago Cubs.

Laureano has been excellent with the Padres, batting .269 with nine home runs, 30 RBIs, and an .812 OPS in 198 plate appearances. We certainly won’t be surprised to see the Padres pick up his $6.5 million club option for 2026 and ensure he remains a dependable right-handed bat in a lefty-heavy lineup.

Miguel Andujar, DH, Cincinnati Reds

Cincinnati entered Thursday only one game behind the New York Mets for the NL’s third and final Wild Card spot, and it’s hard to imagine where the Reds would be without Andujar. Acquired from the Athletics for minor-league pitcher Kenya Huggins, Andujar has crushed opposing pitching to the tune of a .349 average, four home runs, 16 RBIs, and a .956 OPS in 93 plate appearances.

It’s been a frustrating few years for Andujar, the 2018 AL Rookie of the Year runner-up who eventually flamed out with the Yankees. After flashing with the A’s last year, the 30-year-old Andujar has spent the season reviving his career and proving that he’s not done just yet. We’ll see whether the Reds intend to re-sign Andujar, a pending free agent on a one-year, $3 million deal.

For now, the Reds need Andujar to pick it up in the season’s final days and try to leave a lingering quad injury in the rearview mirror as best he can.

Shane Bieber, SP, Toronto Blue Jays

We acknowledge that comparing Bieber, the 2020 AL Cy Young winner and a two-time All-Star, to the likes of Caballero or Andujar is unfair at first glance. However, Bieber has been his typical efficient self since returning from Tommy John surgery, posting a 3.57 ERA and a 34-5 K-BB ratio in 35 1/3 innings for the AL East-leading Blue Jays.

It’d be unfair to omit Bieber from a list like this solely because of his resume. Bieber has allowed two or fewer runs in four of his starts, and his 3.6% walk rate is well below his career 5.4% average. With José Berríos likely headed to the bullpen and Chris Bassitt bothered by a back injury, we expect to see Bieber draw a postseason start — and we’ll see if he can replicate the 2.03 ERA and 15-4 K-BB ratio he recorded in 13 1/3 postseason innings for Cleveland three years ago.

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