Grading Phillies' 2024 Winter Meetings: One huge loss overshadows Romano signing

The Phillies began the week in Dallas on a high note with a low-risk, high-reward signing but finished with a sputter after losing their big trade target.

Philadelphia Phillies president of baseball operations Dave Dombrowski
Philadelphia Phillies president of baseball operations Dave Dombrowski | Bob Levey/GettyImages

The 2024 Winter Meetings have come and gone for another year. It was a hectic few days in Dallas, Texas, with signings, trades and rumors (some true, some not quite as true) abounding day and night.

The Philadelphia Phillies went into the annual gathering of Major League Baseball front offices with a clear to-do list for the offseason. It feels like they just scratched the surface. Not that we thought they'd get everything checked off their list this week, but there's a feeling among fans that the outcome of the Phillies' trip to Dallas could have turned out better.

Phillies president of baseball operations Dave Dombrowski and general manager Preston Mattingly have three areas to focus on to improve the team this winter: the bullpen, the outfield and the starting rotation depth.

Jordan Romano signing began Phillies' 2024 Winter Meetings on a high note

On Monday, they got one thing checked off with the signing of veteran reliever Jordan Romano. It may not be the big splashy signing fans were hoping for (ahem, Tanner Scott). Still, the former Toronto Blue Jays closer agreeing to a one-year, $8.5 million contract to prove himself for a bigger payday next season is a low-risk, high-reward venture.

That is unless the right-hander doesn't work out as the Phillies envision and that's the only high-leverage addition they make before next season. There's still room for another arm at the back end of the bullpen. Whether the payroll constraints allow that to happen remains to be seen.

As sneaky good as bringing in Romano could turn out to be, the move was overshadowed by a lack of subsequent moves and one huge loss.

Missing out on Garrett Crochet was a tough loss to take at the Winter Meetings

On Wednesday, the big news dropped that the Chicago White Sox and Boston Red Sox agreed to a blockbuster trade for one of the Phillies' top trade targets, left-hander Garrett Crochet. It was a dagger for Phillies fans who had been hoping to see the strikeout machine playing his home games at Citizens Bank Park in 2025.

After heavily pursuing Crochet at the trade deadline, the Phillies renewed talks with the White Sox but to no avail after refusing to offer as much as they did in the summer. Chicago was adamant about wanting stud pitching prospect Andrew Painter in the deal. Dombrowski, who has been more than happy to trade top prospects in the past, was adamant about keeping Painter in Philadelphia. It's not like they didn't put an enticing offer out there.

According to The Athletic's Matt Gelb, the Phillies offered their No. 1 and No. 3 prospects Aidan Miller and Justin Crawford at the trade deadline (subscription required), plus some other lower-level prospects. This time around, they weren't willing to pony up Miller again. In the end, it seems they just didn't want Crochet that badly.

Phillies' 2024 Winter Meetings grade

All the Phillies can do is move on to the next target. There's still plenty of work to be done before the team gathers in Clearwater in February. We'll all have our fingers crossed that more moves are coming. From Dombrowski's comments, it sounds like there will be.

“I wish we would have maybe done a little more,” Dombrowski said on Wednesday from the Winter Meetings, per MLB.com's Todd Zolecki. “We just didn’t feel comfortable. But it’s not done either. The Meetings are done, but the conversations aren’t over. You have to be careful. We had a couple conversations that were going yesterday that were quite heavy. They didn’t happen. Then all of a sudden, it’s, 'What about this? What about that?' I said, 'Hold on, let’s take a step back. We don’t have to force anything.'"

As for this week at the Winter Meetings, That Ball's Outta Here officially grades the Phillies' performance as a C. Even though they tried to make a huge splash, they couldn't get the job done. At the end of the day, you either do or you don't.

Phillies' 2024 Winter Meetings grade: C

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