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Is a multi-year deal in Didi's future?

November 19, 2019

After playing his way through a 2019 campaign limited by his return from Tommy John surgery, Didi Gregorius could very well be swapping uniforms in the coming months. Below is a list of the latest news and rumors surrounding the 29-year-old shortstop, who is now a free agent.

After playing his way through a 2019 campaign limited by his return from Tommy John surgery, Didi Gregorius could very well be swapping uniforms in the coming months.

Below is a list of the latest news and rumors surrounding the 29-year-old shortstop, who is now a free agent.

A three-year contract for Didi?

Nov. 19: Gregorius' free-agent walk year couldn't have gone much worse. After back-to-back seasons with 4-plus Wins Above Replacement, per FanGraphs, Gregorius underwent Tommy John surgery and missed the first two months of the 2019 campaign. When he returned, he hit .238/.276/.441 and recorded 0.9 fWAR over 82 games.

The 29-year-old is seemingly a candidate to sign a one-year "pillow contract," which would give him the opportunity to rebuild his value before testing the free-agent market again next offseason. However, George A. King III of the New York Post reports that some teams think Gregorius has done enough to land a multi-year deal. One talent evaluator went as far as predicting a three-year contract for the shortstop, according to King.

“When he came back, there was enough there to believe he could return to the player he was before he was injured,’’ a scout told King.

Gregorius is by far the most accomplished free-agent shortstop on the market, which also includes José Iglesias, Adeiny Hechavarría and Jordy Mercer. That factor could help him in negotiations. However, it's important to note that Marcus Semien, Andrelton Simmons and Jonathan Villar can become free agents in a year, and that Francisco Lindor might be available in a trade.

Is a return to Yankees still a possibility for Gregorius?

Nov. 15: When the Yankees chose not to present Didi Gregorius with the one-year, $17.8 million qualifying offer in early November, it seemed like a sign that the club was ready to move on from the shortstop who so deftly replaced Derek Jeter.

But perhaps that's not the case?

While Yankees GM Brian Cashman has indicated that the team is comfortable with its in-house infield options -- namely, shifting Gleyber Torres to short full time and putting DJ LeMahieu, who played all over the infield in 2019, at second base -- there's at least the possibility that Gregorius could return. More >

Yankees not expected to pursue Didi 'very aggressively'

Nov. 13: The Yankees opted not to extend a one-year, $17.8 million qualifying offer to Gregorius last week, and it doesn't appear as though re-signing the shortstop is high on the team's list of priorities. Citing talks with industry people, SNY's Andy Martino reports that New York is not expected to pursue Gregorius "very aggressively."

Martino was previously told by a source that it was "a very close call" whether Gregorius would be back in the Bronx because the 29-year-old's camp does not think he needs to sign a one-year "pillow contract" to re-establish his value.

The Yankees are keeping a close eye on the $208 million Competitive Balance Tax threshold, and choosing to move on from Gregorius would give the team more flexibility to pursue upgrades elsewhere.

If Gregorius walks, the club has the option of moving Gleyber Torres to short and using DJ LeMahieu at second base on a permanent basis after he filled a utility role in 2019. The Yanks would still have Gio Urshela and the returning Miguel Andújar at third base and Luke Voit at first.

Williams: 'I loved having' Didi

Nov. 12: Reds president of baseball operations Dick Williams only stoked the rumors linking Gregorius to Cincinnati on Tuesday at the GM Meetings.

"I loved having him there," Williams said of Gregorius' time in the Reds organization prior to his trade to the D-backs after his first MLB season in 2012. Williams said Gregorius was "incredibly popular," a "great teammate" and a "great communicator."

MLB Network insider Jon Heyman previously reported the Reds' interest in a reunion with the free-agent shortstop. Gregorius signed his first professional contract with the Reds back in 2007.

Didi reportedly receiving interest from Reds; NY return 'a very close call'

Nov. 8: At the end of the 2018 season, it seemed like a sure thing that Gregorius would be a long-term fixture in the Bronx. But after undergoing Tommy John surgery last October and then struggling in 2019, the shortstop did not receive a one-year, $17.8 million qualifying offer from the Yankees.

An industry source told SNY's Andy Martino that it is "a very close call" whether Gregorius will be back with the team. According to Martino, Gregorius' camp does not think he needs to sign a one-year "pillow contract" to re-establish his value.

The 30-year-old, who produced 8.8 FanGraphs Wins Above Replacement over 2017-18, is easily the top option in a weak class of free-agent shortstops. Not having the QO should help his market, as teams won't need to forfeit a Draft pick to sign him.

According to MLB Network insider Jon Heyman, the Reds, Gregorius' original team, have interest in a reunion.

MLB Trade Rumors previously predicted the shortstop would land with the Reds on a three-year, $42 million deal, and's Mark Sheldon on Friday broke down the reasons why it would make sense for Gregorius to return to Cincinnati.

Would Tribe tab Didi to fill Lindor's shoes?

Nov. 7: Gregorius already has experience replacing one beloved shortstop in Derek Jeter. Could he be asked to do so a second time?

ESPN's Buster Olney writes (subscription required) that it's not a matter of "if" Cleveland will trade Lindor, but when, considering that he would in all likelihood depart for a substantial free-agent deal after the 2021 season. And if the Indians move forward with a deal this offseason, former Mets general manager Steve Phillips believes Gregorius could fill that big shortstop hole in Cleveland. Speaking on MLB Network radio Thursday, Phillips said the free agent could be an ideal safety option if Lindor is indeed dealt.

"I look at Francisco Lindor being traded and Didi Gregorius being the replacement at shortstop in Cleveland,” said Phillips. “[They could sign him to a] five-year deal, for $60 million, and you’ve got cost containment for the next five years. Lindor is going to be a $20 million guy, so why not lock in Didi, and let him be your guy for the next five years? To me, that’s the fallback if Lindor gets dealt.”

Could Didi return to Bronx even without qualifying offer?

Nov. 4: The Yankees' decision to not extend a qualifying offer to Gregorius could help open up the market for the free-agent shortstop. That said, Gregorius could also return to New York on a new deal.

Gregorius, who turns 30 in February, is coming off an injury-shortened 2019 season in which he hit .238/.276/.441 with 16 homers and 61 RBIs in 82 games. Though he has said he hopes to remain with the Yankees, Gregorius will be testing free agency for the first time in his career -- and can now do so without being attached to a compensatory Draft pick for potential suitors.

While it's certainly possible that Gregorius could work out a new contract with the Yankees, the club could also decide to simply shift Gleyber Torres to shortstop and have DJ LeMahieu -- a three-time Gold Glove winner at second base -- return to his natural position.

Without a qualifying offer attached to Gregorius, however, he figures to garner plenty of interest from teams looking for a veteran presence up the middle. For starters,'s Mark Feinsand suggests the Brewers, Phillies and Reds could all make a play for Gregorius this winter. The Marlins could also be among the clubs that reach out to Gregorius in the coming weeks, according to's Joe Frisaro.

CBT concerns could affect Yanks' plans for Didi

Nov. 3: Would the Yankees let Gregorius leave via free agency -- and choose not to extend him the one-year, $17.8 million qualifying offer -- in order to go after the top free-agent starting pitchers?

The answer could come down to payroll math. Aroldis Chapman's reworked contract keeps the Yankees' payroll situation relatively neutral in comparison to his former deal, but New York's competitive balance tax (CBT) considerations could still affect their ability to go after Gerrit Cole or Stephen Strasburg this offseason.

Writing for the New York Post on Sunday, MLB Network insider Joel Sherman estimates that Chapman's $48 million salary over the next three seasons will cost the Yanks roughly $17.5 million annually toward the CBT payroll. Adding that figure to the Yankees' signed players, arbitration-eligible players and handful of non-arbitration-eligible players that the club needs to sign to fill out the roster, Sherman estimates that New York will be right up against the $208 million threshold for the first CBT penalty (20% tax on all overages for first-time offenders). That means the Yankees would have roughly $20 million to spend before triggering the second CBT penalty (additional 12% surtax), and roughly $40 million before triggering the third and final penalty (42.5% tax).

The Yankees have been hesitant to cross the CBT threshold in past years (the Red Sox notably did so while assembling their 2018 World Series champion roster), but the pressure to spend might be heightened in the Bronx after New York finished the 2010s without a single American League pennant. Extending the qualifying offer to Gregorius could, therefore, limit their ability or desire to spend even more money in the free-agent market and thus run the risk of incurring further CBT penalties. The deadline for teams to extend qualifying offers to their impending free agents is Monday at 5 p.m. ET.

Would Yanks move Andújar, keep Didi?

Nov. 2: The Yankees' constant injury woes this year were well documented, but the pinstripes seem to have plenty of infield depth. Does that automatically mean they should let Gregorius walk away in free agency?

FanGraphs' Dan Szymborski argues instead that the Yankees should not only extend Gregorius the qualifying offer, but also consider trading third baseman Miguel Andújar to clear up New York's infield logjam and leave room for Gregorius. Andújar finished runner-up to Angels star Shohei Ohtani in the 2018 American League Rookie of the Year Award vote, but he appeared in just 12 games this season before tearing the labrum in his right shoulder and undergoing surgery in May. He was an excellent hitter in '18, but continuing questions about his defense precludes him from being a no-doubt starting candidate for the Yankees in 2020.

Gregorius, Szymborski points out, was worth nearly 5 fWAR as recently as 2018, and the Yankees might be wiser to bank on him returning to form. At the very least, Szymborski argues that New York should extend the qualifying offer to him to receive some form of compensation, should he ultimately sign elsewhere.

Yanks mum on Didi, but indicate he could be back

Nov. 1: According to SNY's Andy Martino, the Yankees are keeping their intentions regarding free agent shortstop Didi Gregorius quiet, but do "like him as a person and see him as a bounce-back candidate as a player."

Gregorius was hurt for much of last season, and over 82 games, struggled to a .238/.276/.441 slash line, though he did hit 16 home runs. But he's still 29, and a season removed from career highs in homers (27) and OPS (.829).

With Gregorius a free agent, New York does have an infielder who can play shortstop in Gleyber Torres, who filled in for him at the position while he was sidelined last season.

Reds pick up Galvis' option; does Didi still fit?

Nov. 1: After making his Major League debut and playing eight games for the Reds in 2012, Gregorius was sent to the D-backs as part of a three-team, eight-player trade that also included the Indians. Seven years later, could the veteran find himself back in Cincinnati?'s Mark Sheldon suggested earlier this week that the Reds could take a look at the free-agent shortstop this offseason. Cincinnati has an opening at that position, with José Iglesias also hitting the open market. The Reds exercised Freddy Galvis' $5.5 million club option for 2020 on Friday, but Sheldon doesn't think that will prevent the team from pursuing another shortstop.

Galvis does have extensive experience at short, but he doesn't really solve the team's need for an offensive upgrade, as he's a lifetime .248/.291/.384 hitter, albeit one who produced personal bests in homers (23) and OPS (.734) last season.

Gregorius is coming off a poor season with the Yankees, missing April and May while recovering from Tommy John surgery and then hitting just .238 with a .276 on-base percentage in 82 games. But prior to 2019, Gregorius produced back-to-back seasons with a FanGraphs Wins Above Replacement total above 4.0, slashing .277/.326/.486 in that span, and he could be more affordable after his down year.