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The 2021 version of shortstop Didi Gregorius clearly wasn’t what the Philadelphia Phillies signed up for. All aspects of Gregorius' game took a step back. On top of his on the field struggles, he was once again plagued with an elbow issue. After signing a two-year, $28 million deal to return to Philadelphia in Jan. 2021, the expectation was that Gregorius would bridge the gap at shortstop to Baseball Prospectus' #67 overall prospect Bryson Stott.

Between Gregorius’ struggles and Stott’s success in the minors and Arizona Fall League, that timeline has been pushed up. President of Baseball Operations Dave Dombrowski even went as far to advise Stott to come into camp ready to win the job. If that were to be the case, what then becomes of Gregorius and the $14 million he’s owed this year?

The simple solution in the minds of many fans is to trade Gregorius. Unfortunately, the list of teams looking to trade for declining players with bigger salaries is never long. Therefore, expectations must be lowered for any potential return.

No team is likely to give up valuable prospects for a player in Gregorius’ circumstance. Instead, there seems to be a few options. 

Option #1: Attach a prospect to him in order to sweeten up a deal.

Potentially, the top talent that the Phillies could aim for is Chicago White Sox closer Craig Kimbrel.

Chicago White Sox Closer Craig Kimbrel

Chicago White Sox Closer Craig Kimbrel

With an already deep bullpen and a price tag of $16 million this year, the White Sox will be motivated to move Kimbrel. Gregorius would add a lefty to the high powered, but righty heavy offense while cutting salary as well. Attaching a mid-to-low level prospect should help to get a deal done.

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From Philadelphia’s perspective, adding Kimbrel would allow them to utilize Corey Knebel in other high leverage situations. Effectively, they would have their closer for only $2 million extra. Doing so would greatly bolster the Phillies’ pen and audition both guys for the role moving forward.

Should the club feel content with Knebel as the closer for next year, they still have a gaping hole in center field. While higher quality options were recently discussed in the Inside the Phillies mailbag, dealing Gregorius for a lower caliber player could be a fallback option if they fall flat.

Option #2: Offload some salary for a lower quality player. 

The last few years of Gregorius’ free agency, the Cincinnati Reds were rumored to have interest. Therefore, they make a lot of sense as a trade partner.

Two potential targets emerge here in outfielders Tyler Naquin and Shogo Akiyama. Naquin is owed only $1.5 million this year and played well for the Reds slashing .270/.333/.477 across 127 games. Unfortunately this makes the Reds unlikely to move him in this deal.

Instead, Cincinnati would almost assuredly jump at the opportunity to move on from the final $7 million owed to Akiyama this year. He’s been disappointing since his arrival in the United States two years ago, but was described at the time as a plus defender with a solid hit tool. The bat has certainly not translated to MLB, yet this still represents an opportunity for Philadelphia to cut $7 million from their payroll and take a shot on Akiyama as a defensive-first center fielder.

Option #3: Keep Gregorius and hope he bounces back. 

With the universal designated hitter likely coming, having Didi's left-handed pop could help the team even if his best defensive days are behind him. If the Phillies don’t have someone in mind to allocate the payroll cut from a potential deal, a rebounded Gregorius would be more beneficial. Unless a deal like Kimbrel for Gregorius nearly straight up presents itself, expect Dombrowski to bring him back in some capacity.

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