Could the Philadelphia Phillies “luck” into re-signing Didi Gregorius?

Didi Gregorius market could be back on for the Philadelphia Phillies.

The 2021 MLB season is right around the corner…and Didi Gregorius is still a free agent. For the Philadelphia Phillies, this can only be viewed as a favorable situation. It appears no team is itching to sign the veteran shortstop, which could mean a return to Philadelphia isn’t 100% out of the picture just quite yet.

According to Jim Salisbury of NBC Sports Philadelphia, a good market just hasn’t really shaped up for the former Phillie:

“But, as we said, it’s now mid-January. The markets for a number of quality free agents, including Realmuto and Gregorius, have not developed the way they had hoped back in November. Realmuto saw a potential landing spot dry up when the Mets signed James McCann to be their catcher. Gregorius remains a free agent in a market that still includes Marcus Semien and Andrelton Simmons — and the shortstop market will be even more crowded next winter.”

When the Phillies declined to extend a qualifying offer to Gregorius back at the start of the offseason, many felt it was a sign of the organization committing to moving on from the fan-favorite shortstop. While that may have been the plan initially, things do change. The Phillies have a completely new front office, headlined by a President who likes to spend money, and Didi remains a free agent in mid January.

With all of this in mind, Salisbury also noted that the Phillies remain “engaged” with Gregorius (along with catcher J.T. Realmuto):

“The Phillies continue to be engaged with both Realmuto and Gregorius…Early in the offseason, there was pessimism that the Phils would sign either of these guys. Now, we wonder if there’s a way they could end with both.”

The qualifying offer that the Philadelphia Phillies declined to offer Didi a few months ago was roughly $18 million. Considering the fact that the market for Didi hasn’t really shaped up the way we all envisioned, there’s a pretty solid chance that Didi will end up taking less than $18 million this winter. If that number comes back down to around $14-15 million, it wouldn’t surprise me if Dombrowski pushed to bring him back for the 2021 season (and beyond). Shortstop is still a major position of need for the Phillies at the moment, and Gregorius was a near perfect fit last year.

Like all things, a potential Didi/Philadelphia reunion will ultimately come down to the money. While the free agent market seems fairly dry this offseason, Didi is coming off a fantastic 2020 campaign – a team will sign him eventually. However, as far as things go with the Phillies, it’s hard not to feel like things are progressing towards a favorable outcome. A few weeks ago and re-signing Gregorius felt impossible, now we at least know the two sides are still communicating.