No. 6: Phillies sign Trea Turner to an 11-year deal on Dec 5 , 2022
The Phillies' most recent big Winter Meetings signing was only a year ago. Although for Trea Turner, his first season in Philadelphia might have felt more like a decade with the ups and downs he went through.
Fresh off their World Series defeat at the hands of the Houston Astros, the Phillies landed one of the biggest free agents on the market when they inked Turner to an 11-year, $300 million contract. It's a deal that will see him in red pinstripes through the 2033 season, in theory.
At the time, the move was deemed a massive success for Dombrowski and Fuld. About halfway through the 2023 season, however, the tide had turned as the two-time All-Star shortstop struggled through the worst season of his illustrious career with a paltry .247 batting average and .687 OPS at the All-Star break.
As it turned out, once Turner locked in, he helped catapult the Phillies to a 90-win season and the top Wild Card spot before helping guide them to within a couple of victories of the World Series. It wasn't the outcome many had hoped for (or assumed) when he was first signed, as a second consecutive trip to the Fall Classic was on everyone's minds.
There's still plenty of time for Turner to prove his Winter Meetings signing to be an even bigger franchise move, with the team's core poised for another few years of deep playoff runs. If he helps capture the Phillies' next title, the signing may be higher up the next iteration of this list.
NEXT: Another recent Winter Meetings signing added a top-end starter to the rotation.