The July 30 trade deadline came and went without a Garrett Crochet deal, even though several teams reportedly had interest in the White Sox southpaw.  The Dodgers and Phillies were two of the clubs involved in Crochet’s market, and while The Athletic’s Ken Rosenthal reports that the two NL contenders made “attractive” offers to the Sox, the bidding only went so far.

Beginning with the Phillies, they weren’t willing to include Andrew Painter, who remains a top-34 prospect in the view of both Baseball America (20th) and MLB Pipeline (34th) even though he hasn’t pitched since September 2022.  A UCL sprain sidelined Painter during Spring Training 2023 and he underwent a Tommy John surgery in July 2023, putting the highly-touted righty on pace to be ready for the start of the 2025 campaign.

The 13th overall pick of the 2021 draft Painter has only pitched 109 2/3 pro innings, including 28 1/3 innings at the Double-A level.  He could start 2025 back at Double-A if the Phillies want to relatively ease him back into action after his long layoff, though if all goes well, Painter could move up the ladder pretty quickly and become an option for Philadelphia’s big league staff before the end of next season.  Since Painter is still just 21 years old, it is understandable why even a win-now team with a pretty crowded pitching staff would be wary about moving a top prospect with front-of-the-rotation potential.

Rather than make a big splash of a Crochet trade, Philadelphia instead made a more modest set of moves prior to the deadline.  The Phillies’ discussions with the White Sox about Crochet might’ve spun off into the trade that brought Tanner Banks to Philadelphia, and the Fightins’ deadline adds also includes the likes of Carlos Estevez and Austin Hays.

Chicago’s talks with Los Angeles were still ongoing in the last hour before the deadline, before the Dodgers apparently pivoted and instead landed Jack Flaherty from the Tigers.  Since Flaherty is a free agent after the season and his trade market may have been impacted by some injury concerns, naturally the Tigers’ ask for the right-hander was much lower than what the White Sox were seeking for Crochet, who is arbitration-controlled through the 2026 season.

Top catching prospect Dalton Rushing wasn’t included in the Dodgers’ offers for Crochet, but River Ryan was, though Rosenthal notes that “the White Sox had concerns about [Ryan’s] health.”  Chicago’s focus was on the shoulder problem that cost Ryan the first two months of the minor league season, but Ryan has since been sidelined by a Tommy John surgery that will likely keep him out of action for the entirety of the 2025 campaign.

The Dodgers had such a need for pitching that Ryan got a bit of a fast track to the majors following his shoulder injury, as Ryan amassed only 24 1/3 innings in the minors (16 1/3 at the Triple-A level) this season before he was called up for his MLB debut.  To this end, moving a big league-ready starter for Crochet probably wasn’t an ideal scenario for an L.A. team that basically needs all the arms it can get at this point, yet the Dodgers were obviously going to have to give up a lot to pry Crochet away from the White Sox.

Rushing’s name has been involved in trade speculation even before Will Smith signed his big contract extension with Los Angeles in March.  Smith’s status as the Dodgers’ catcher of the foreseeable future could make either Rushing or fellow catching prospect Diego Cartaya expendable, yet it could be that L.A. didn’t want to move Rushing before experimenting with him at another position.  Rushing has been playing only left field since his promotion to Triple-A earlier this month, and he has kept up the hot hitting even while adapting to a new position and facing a higher caliber of pitching, so it isn’t out of the question that Rushing could make his Major League debut before 2024 is over.

In another note about the Crochet trade talks, Rosenthal writes that “the White Sox also entertained offers in which they would have received lesser [prospect] packages but gained salary relief.”  These particular discussions reportedly involved Andrew Benintendi, so in this scenario, an unknown team would’ve eaten all or most of Benintendi’s remaining contract as a sweetener to obtain Crochet.  Rosenthal didn’t specify which teams made such offers, though the Dodgers and Phillies both seem less likely candidates, as adding Benintendi’s contract would’ve come at an even heftier cost for two teams deep into luxury tax territory.

On the one hand, Benintendi’s five-year, $75MM contract is already looking like a misfire less than two seasons in, so packaging him along with Crochet might be Chicago’s only reasonable method of getting Benintendi off the books.  That being said, Crochet is also the team’s best trade asset, and moving him for a prospect package of maximum value is a clear way for the Sox to bring more talent into the organization.  Diluting that return just to save some money wouldn’t seem all that prudent, especially since the White Sox reduced payroll in other deadline deals.  Benintendi is owed $47.5MM over the 2025-27 seasons, but the Sox have just under $41MM committed to their entire 2025 payroll, as per RosterResource.