What happens if the Phillies re-sign Didi Gregorius?

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The Phillies have two starting jobs for three middle infielders; what happens now?

The Phillies went into 2020 with Didi Gregorius at shortstop, Jean Segura at third base, and Scott Kingery at second base. While there were some question marks — such as whether Segura could handle the hot corner defensively, or if Kingery could finally have a productive season at the plate — there were also reasons to be excited.

Kingery was finally getting a starting job at his best position, and Gregorius was all but certain to be the best Phillies shortstop since prime Jimmy Rollins.

However, Kingery quickly lost his permanent job, as he struggled with injuries and poor performance. It didn’t help Kingery that Alec Bohm came up and quickly earned a job as the starting third baseman — pushing Segura over to second base and leaving Kingery with nothing.

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Gregorius is now a free agent; many Phillies fans, myself included, would like to see the team re-sign him. Not only is Gregorius a fun player both on and off the field, but he was one of the most consistent hitters in the middle of the lineup.

If the Phillies do re-sign Gregorius, however, they would have a problem. What are they going to do with Kingery and Segura? Here are the team’s options.

Option #1: Don’t Sign Didi Gregorius

If the team misses out on Didi Gregorius, they could try to sign another shortstop, like Marcus Semien, or they could sign a new second baseman, like DJ LeMahieu, and move Jean Segura back to short. However, if the Phillies don’t re-sign Didi, the most likely scenario is that they go into 2021 with Segura and Kingery starting in the middle infield.

This seems like the worst option. Simply put, neither Segura nor Kingery is as good a player as Gregorius, and this team needs to improve if they want to make the playoffs next season.

However, it may be the most likely scenario. The Phils’ payroll is reportedly likely to shrink next year. With two capable middle infielders already in the fold, the Phillies’ brass may prefer to spend money in other areas.

Didi Gregorius #18 of the Philadelphia Phillies (Photo by Mitchell Leff/Getty Images) /

Option #2: Sign Didi Gregorius to play SS, and let Jean Segura play 2B

This is the move that a win-now team should make. Gregorius and Segura are both strong hitters, and on a healthy Phillies team, they would likely be hitting in the bottom half of the order. Just typing that sentence makes me excited for the Phillies’ offense next year.

But where does this leave Kingery? The team can trade him, but after a poor 2020 season, his trade value will be extremely low. The Phillies likely won’t want to trade a former top prospect for peanuts.

If the Phillies keep Kingery, he’ll be forced into a super-utility role once again. It’s clear that Kingery does not thrive in this role. He’s struggled offensively for three seasons now, and he believes that one of the main reasons for that is the stress of not having a primary position.

While this may be the best option for the 2021 team, it would essentially mean giving up on Scott Kingery.

Option #3: Sign Didi Gregorius to play SS, and let Scott Kingery play 2B

For this scenario to work, the Phillies would have to trade Segura.

Poor Jean Segura. He’s a good ballplayer and seems like a really nice guy, but he’s already been traded four times in his career.

However, trading Segura is certainly the least likely option. First of all, he has a full no-trade clause in his contract, so he’d have to agree to a trade. Furthermore, it might be hard to find a team willing to take on the $29.5 million remaining on his contract,

If the Phillies can trade Segura, though, it may be the “best of both worlds” option. This way, the Phillies get to keep Didi Gregorius, their best middle infielder from 2020, but they also get to give Kingery a real chance to prove himself.

On the other hand, if Kingery continues to play as badly as he did in 2020, this option could be disastrous for the Phillies. The bottom third of the order could be a real black hole with Kingery, Quinn/Haseley, and an unknown DH.

There are pros and cons to all three options:

Option #1 would give the Phillies more payroll flexibility, which they can use to improve the pitching staff, but it significantly downgrades the middle infield.
Option #2 would give the Phillies a fearsome offense in 2021, but means throwing Scott Kingery to the curb.
Option #3, meanwhile, is the “best of both worlds” scenario, but it’s also extremely unlikely to happen.

Which option do you think is the best? Which do you think is the most likely to happen? Sound off in the comments below!

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