The Phillies must overpay to keep Didi Gregorius

Didi Gregorius at shortstop for the Phillies
How much will Gregorius command as a free agent? Photo from NBC Sports.

The Philadelphia Phillies are heading into an offseason with a long list of questions to answer once again. The furore over the Bryce Harper pursuit and the J.T. Realmuto trade have not reaped the desired rewards. Didi Gregorius and Realmuto, two of their top five most valuable hitters in 2020, are both heading for free agency.

Realmuto will be an offseason target for a lot of MLB‘s big-market teams, including the Phillies division rivals New York Mets. Gregorius’ market is more complex. There’s an all-time free agent shortstop class coming after the 2021 season – teams who have a need at the position might be waiting to swing big for Trevor Story, Corey Seager, Francisco Lindor, Carlos Correa or Javier Baez.

Gregorius and Marcus Semien are the premier shortstop options in the 2020/21 offseason. Defensive master Andrelton Simmons is on the market, too. Semien had a down year in the shortened 2020 season after getting plenty of MVP support in 2019. Gregorius got MVP votes in 2017 and 2018, was injured in 2019 and massively overperformed his expected numbers in 2020.

Worrying numbers

The former Yankee was in the 29th percentile of expected weighted on-base average at .298 but his wOBA was up at .342. Statcast has never loved Gregorius – he doesn’t hit the ball that hard, and he’s benefited from playing at Yankee Stadium and now Citizens Bank Park.

Concern about Gregorius from an analytics perspective isn’t new. He’s ranked in the bottom eight percentage of the league in exit velocity twice before, but registered a career low of 83.8 mph in 2020, putting him in the bottom 2% of hitters. There has been a marginal drop in sprint speed over the last couple of seasons too, and questions about his defensive ability have been exaggerated rather than answered.

Gregorius’ first step is not what it was, and heading into his age-31 season, that’s unlikely to improve. Baseball Savant’s infield outs above average showed he struggled coming in to balls in 2019 and 2020.

Potential Gregorius contract

A long-term deal, which seemed inevitable when Gregorius was playing so well for the Yankees in 2018, is no longer a guarantee. Heading into a pandemic-impacted offseason, no team should be looking beyond three years for Gregorius. A one-year deal doesn’t work for Gregorius but it might be the best thing for the Phillies.

This is where the future of Realmuto is so important. Committing $20 million or more to Realmuto per season, with Rhys Hoskins‘ contract to come and Harper signed until the end of time, might make a big shortstop free agent signing unlikely. As is so often the case in MLB, Gregorius’ next move could depend on the willingness of Phillies ownership to spend. They were seventh in payroll in 2019 and 10th in 2018.


The Phillies have not made the playoffs since 2011. Penny pinching after signing Harper would seem illogical. How do they see this team? Owners don’t like spending on non-competitive rosters. Do they think a big signing or two can make them contenders? Or have they grown frustrated at consecutive seasons below .500 despite such a hefty payroll?

NBC Sports tabbed Gregorius at a three-year, $45 million contract. Such a deal seems ambitious. One year at a higher AAV or two for $28-32 million is more reasonable. If Phillies ownership is willing to pay Realmuto and pursue one of the superstar shortstops next offseason, they should look to tempt Gregorius with a one-year pact. He will want to avoid being a free agent next winter, but there’s unlikely to be a huge market for him on a multi-year deal. Maybe he’s tempted by $20 million for 2021.

Gregorius landing spots

The Yankees aren’t thought to be too keen on Gregorius, but they could get involved if he’s forced to settle for a one-year deal. The Angels are worth keeping an eye on if Simmons goes elsewhere, too.

Overpaying for Gregorius in free agency can make sense for the Phillies. A multi-year deal is hard to justify – they should pursue Semien if they want to find their long-term shortstop this offseason. Chucking a big number at Gregorius in 2021 gives them a good shortstop next season, and enables ownership to pursue another franchise star in next winter’s free agency.

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About Sam Cox 513 Articles
Sam is a widely published freelance writer, covering basketball, baseball and a range of other sports. He's still trying to decide if he prefers a rundown shot block or a smooth double play.

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