Leading up to baseball’s winter meetings, we will take a daily look at some of the game’s top free agents and how they could potentially impact the Phillies.

Our Phillies free-agent targets series continues today with Didi Gregorius, who has been connected to the Phils in recent days.

The vitals

Gregorius is a solid defensive shortstop who can hit for power and for average. From 2016-18 with the Yankees, he averaged 24 homers per season and hit .277 with an OPS eight percent above the league average. 

He did benefit from the short porch at Yankee Stadium, but that short porch can work both ways, also playing tricks on homer-happy hitters. It stands to reason that in another park, Gregorius' batting average and doubles would increase while the homer total would decrease slightly.

Gregorius will play the 2020 season at age 30. He underwent Tommy John surgery in October 2018 and missed half the season in 2019. He hit just .207 with a .250 on-base percentage after Aug. 1, but he did go 4 for 10 with a homer and six RBI in the ALDS win over the Twins.

Why he fits

The Phillies need a better defensive shortstop with more range. Jean Segura committed 20 errors last season, but beyond that, his waistline grew throughout the summer and it wasn't a defensive season that could have inspired much confidence from the Phillies as he ages.

Gregorius is the best shortstop on the market. He could push Segura over to second base, thereby creating an everyday spot for Scott Kingery at either third base or center field. For all the hand-wringing the last two years at the Phillies' use of Kingery all over the diamond, Kingery's flexibility has created flexibility for the Phillies, who are not boxed in to upgrading a specific position.


Signing Gregorius could also make Segura a trade candidate, but how much value would the Phillies get for him? Segura has approximately $43 million remaining over the final three years of his contract and is coming off his worst season in five years. In this scenario, it probably would make more sense for the Phillies to hold on to Segura in hopes that he rebounds to hit over .300 as he did each season from 2016-18.

Gregorius' left-handed bat would help balance out a Phillies lineup that has Bryce Harper but no other lefty power threat currently projected to start.

Why he doesn't fit

Do the Phillies really need to sign a shortstop? Even if they're skeptical Segura can handle the position moving forward, they could simply move Kingery to shortstop and find another starter to play third base or center field. 

Josh Donaldson, for example, is a better hitter than Gregorius. Offensively, the Phillies would probably be better off (at least in 2020) with Donaldson at third and Kingery at short than with Gregorius at short and Kingery at third.

Mike Moustakas? The Moustakas vs. Didi comparison is pretty close, with Moustakas providing more power and less of an injury history and Didi holding the advantage in speed and athleticism. 

There aren't many worthwhile free-agent options in center field, the Phillies' other position of need. Thus, you'd figure the position player upgrade will come at either third base or shortstop.

Scout's take

"He's a leader on and off the field and a quality player offensively and defensively. He looked more and more healthy as the season went on and his arm was almost back to full strength."

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