DALLAS — The Phillies left these Winter Meetings with a surge; no team selected more players (six) in the minor-league phase of Wednesday’s Rule 5 draft than they did. Someone has to play at Double A in 2025. As the large conference room at the Hilton Anatole emptied, president of baseball operations Dave Dombrowski surveyed the landscape.
He’s left wanting something.
“I wish we would have maybe done a little more, but it’s not done either,” Dombrowski said. “The meetings are done. But the conversations we had, it doesn’t mean they’re over. We had a couple of conversations going that were quite heavy and (the potential deals) didn’t happen. And then all of a sudden it’s, ‘Well, what about this one?’ Hold on. Let’s just take a step back. We don’t have to force anything. Let’s just wait and let’s see what happens.”
Dombrowski is not famous for his restraint, but the veteran executive has practiced it while running the Phillies. It was Dombrowski who eight years ago at the Winter Meetings traded Boston Red Sox four prospects to acquire an ace pitcher from the Chicago White Sox. He’s carried a reputation — fair or not — for decimating farm systems to feed a big-league winner. He had a chance to do it again this offseason for Garrett Crochet.
The Phillies resisted. On Wednesday, the White Sox traded Crochet to Boston, the exclamation point to an active week across the sport.
“I’m not sure it was the right time for us to do that right now,” Dombrowski said.
There was a time. Multiple major-league sources portrayed the Phillies and White Sox as near trade partners in July. At one point, sometime close to the July 30 trade deadline, the Phillies upped their offer to acquire Crochet by including Aidan Miller along with Justin Crawford and other lower-level prospects, according to the sources.
Those talks never culminated in an agreement. The Phillies believed they had satisfied Chicago’s stipulation for two top-100 prospects. The White Sox, who had insisted on top pitching prospect Andrew Painter’s inclusion, pushed back. There was no deal. The Phillies, who envisioned the 25-year-old Crochet as a powerful top-of-the-rotation presence for years to come, were disappointed.
But they never offered Miller and Crawford together this offseason when discussing scenarios with the White Sox, according to league sources. Had the Phillies acquired Crochet in July, they would have had him under contract for at least three postseason runs. Crochet has signaled he is open to a contract extension, but the trade was not conditional on a window to negotiate one.
So, for Dombrowski and the Phillies, the calculus changed this offseason.
Painter, considered the lone untouchable in the organization, was never on the table despite Chicago’s continued interest. Some within the Phillies organization ultimately believed they were not close to a Crochet deal without Painter; White Sox officials continued to scout Painter during Arizona Fall League action in October.
But the Red Sox engineered a deal without surrendering their very best prospects and, still, in landing the four-prospect package from Boston, Chicago arguably did better than it would have with the Phillies.
“They got a nice bunch of players,” Dombrowski said.
He listed his reasons for not going all-in.
“We have four quality starting pitchers,” Dombrowski said. “And we have a young pitcher coming right behind them that we really like a whole bundle. So to give up that type of talent …
“One thing we’ve done is we really rode out the development of our farm system over the last few years. And we’re just getting to the point of having the impact that those guys (provide). It’s not quite here, but we’re on the verge of having some really good young players. This is where I disagree with people. ‘The Phillies are in a position where, maybe, their time is ending.’ And I don’t agree with that. I always say it might be that the time for this present roster (is almost ending) because some guys are free agents. But we have some really good young players coming.”
So the Phillies are back to their quest for open-mindedness. Dombrowski acknowledged the No. 5 starter could come from within; the Phillies will bring Taijuan Walker, Mick Abel, Seth Johnson, Moisés Chace, Jean Cabrera, Tyler Phillips, Alan Rangel, Kyle Tyler and others to spring training for a competition. One pitcher who could have factored into that mix, Eiberson Castellano, went to the Minnesota Twins in the Rule 5 draft. The Phillies decided not to protect Castellano by adding him to the 40-man roster. They took a risk.
“We think somebody might have a hard time keeping him,” Dombrowski said. “So that’s what it really came down to.”
The Phillies will continue to explore trades, but even so, Dombrowski has altered his tone. They have not received the level of interest they expected in their available players. They’ll wait to see if that changes once other pieces come off the board. But, by the time the Phillies can make a deal, they have to be able to backfill whomever they flip from their projected roster.
It’s a tricky dance.
Maybe they could have had Crochet. They chose restraint instead.
“Andrew Painter’s pretty good,” Dombrowski said. “We could get a lot of players for Andrew Painter. But I think I’ll wait it out the next few months to get him with us.”
(Photo: Quinn Harris / Getty Images)
