What happens if the Phillies re-sign Didi Gregorius?

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!