MLB Free Agent Profile: Didi Gregorius

MLB Free Agent Profile: Didi Gregorius

by November 14, 2020 2 comments

After the New York Yankees let him walk, Sir Didi Gregorius signed a one-year, $14 million contract with the Philadelphia Phillies last offseason. The deal reunited Gregorius with former Yankees’ manager Joe Girardi who had signed on to be the Phillies’ new manager. The shortstop will turn 31 prior to the 2021 season. He could be putting on the fifth new threads of his career.

In the abbreviated 2020 season, Gregorius was fairly productive; he returned to more of his pre-Tommy John surgery self. With that in mind, let’s take a look at what we can expect his market to look like this offseason.


Defecting to the states

Gregorius signed with the Cincinnati Reds at the age of 17 in 2007. He was discovered by a Reds scout while he was playing in an under-18 tournament in the Netherlands. His professional debut came in 2008 with the Gulf Coast Reds of the Rookie-level Gulf Coast League.

After moving up the minor league system, Gregorius was added to the 40 man roster in 2011 so the Reds could protect him from the Rule 5 draft. He started 2012 with the Pensacola Blue Wahoos, the Reds’ Southern League affiliate. He was then promoted to the Louisville Bats of the AAA International League, where he played in 48 games.

Moving Around

Sir Didi earned a September call-up that season and he made his debut on September 5. He played in eight games that September before being traded as part of a three-team trade with the Arizona Diamondbacks and Cleveland Indians. The Reds sent Gregorius to Cleveland along with Drew Stubbs for Shin-Soo Choo and Jason Donald. The Indians then flipped Gregorius to Arizona along with reliever Tony Sipp and infielder Lars Anderson for pitchers Trevor Bauer, Bryan Shaw, and Matt Albers. Gregorius began the 2013 season in the Diamondbacks’ farm system, before being promoted to Arizona on April 18.

Replacing The Captain

Following the 2014 season, the Yankees were in need of a shortstop after Hall of Famer Derek Jeter retired. In turn, they acquired Gregorius in a three-team involving the Detroit Tigers. New York sent Shane Greene to the Tigers, while the Tigers sent Robbie Ray and Domingo Leyba to the Diamondbacks. In 2017, Gregorius suffered the first major injury of his major league career after he injured his shoulder during the World Baseball Classic. He missed nearly the first month of the season and he made his season debut on April 28. In 2018, he injured his elbow during the ALDS and required Tommy John surgery in the offseason. Since he underwent the surgery in October, he missed the first two months of the 2019 season recovering.


In the 2020 season, Gregorius played in all 60 games and slashed .284/.339/.488 with 10 home runs and 40 RBI. His strikeout rate was among the top three percent of the league at just 11.8%.

Over his five years with the Yankees, Gregorius had a number of iconic moments under the bright lights. That didn’t come with some adjustments, however, as he struggled to fill the giant shoes of Jeter off the bat. He started out hitting .222 within the first two months while committing six errors. After getting an earful from the Yankee faithful, he started to turn things around. He wound up finishing that season with a .265 average and 89 wRC+, along with a 7.5 Ultimate Zone Rating (UZR). In 2016, he had career-highs in hits (155), doubles (32), home runs (20), and RBI (70).

His first really big moment with the Yankees came in the 2017 American League Wild Card Game. With the Yankees already down 3-0 against the Minnesota Twins after the first inning, he hit a huge game-tying three-run homer that erupted Yankee Stadium. In the Yankees 14-12 victory over the Twins on July 23, 2019, Gregorius went 5-for-5 with seven RBI. He hit his 100th career homer in the same game. Then, as if this weren’t poetic enough, he had another huge moment in Game 2 of the American League Division Series against who else, the Twins. With the Yankees already up 3-0 in the third inning, Gregorius came up and whacked a grand slam – the first ever by a Yankees shortstop in the postseason – which sent Yankee Stadium into oblivion.

Ideal Contract

Gregorius could fit with a number of teams in need of a shortstop. A return to Philadelphia isn’t out of the question and a Reds’ reunion could also be in the cards. The ideal situation for Gregorius would be to sign somewhere for a multi-year contract and lock down the starting shortstop role for them. A likely contract could be around two or three-year range, worth about $15 million per year.

Top Landing Spots

Philadelphia Phillies

The Phillies moved Jean Segura off shortstop after signing Gregorius and he played the majority of games at third and second base. They decided not to give Didi the $18.9 million qualifying offer which means it is likely he will go elsewhere. Unless, of course, they can work out a deal and win the bidding war. He was their most consistent hitter in 2020, giving them a reason to offer him a multi-year deal. But if they don’t, they could move Segura back to short.

Cincinnati Reds

The Reds have a notable opening at shortstop for 2021. Freddy Galvis is a free agent, while Jose Garcia still needs some seasoning down in the minor leagues. He would fill a huge need and give them a solid bat in the middle of their lineup. He would also give great leadership to the young Reds squad.

Los Angeles Angels

With Andrelton Simmons headed to free agency, the Angels will need to fill that need. Gregorius would add balance to a predominantly right-handed lineup. He would also be an offensive upgrade over the defensive wizard Simmons, while they would be making a trade-off on defense. Gregorius is solid on defense but is definitely no Simmons. Either way, he would be a great bat to add to a lineup led by Mike Trout and Anthony Rendon.

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Main Credit Image: Embed from Getty Images

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