On Dec. 5, 2014, the Yankees acquired Didi Gregorius from the D-backs as part of a three-team trade that also involved the Tigers. Derek Jeter had just retired, and a new shortstop was needed for the difficult task of filling those shoes in the Bronx.

Five years later, a successful tenure in pinstripes could be coming to an end. With Gregorius a pending free agent, the Yankees have until five days after the end of the World Series to make him a one-year, $17.8 million qualifying offer. If they don’t, or if Gregorius declines the offer, he would hit the open market.

The events of the past year have complicated his situation significantly. On the heels of a career-best season in 2018, Gregorius sustained a right elbow injury during the American League Division Series that required Tommy John surgery and kept him out of action until June. When Gregorius did return, he was unable to replicate his recent level of performance, casting some doubt on his prospects as a free agent.

With that in mind, here are five pressing questions about Sir Didi’s status.

Will he qualify?
The qualifying offer isn’t a slam-dunk case for the Yankees. Gregorius is a popular presence on the team, and an accomplished player. It would hardly be unreasonable for general manager Brian Cashman and company to prioritize depth -- after a season that saw the club face an overwhelming barrage of injuries -- and make a play to keep Gregorius for another year.

At the same time, the Yankees have no shortage of infield options and could allocate that $17.8 million for other needs. Gleyber Torres took another step forward in 2019 and could inherit the shortstop duties he held temporarily during Gregorius’ recovery. DJ LeMahieu can play second base coming off his resoundingly successful Bronx debut, and the Yankees have both 2019 breakout star Gio Urshela and recovering 2018 rookie standout Miguel Andujar for third base. Luke Voit returns at first base, as could Edwin Encarnacion ($20 million club option) and Mike Ford.

While Gregorius could prioritize landing a multiyear deal this winter, the qualifying offer would be difficult to pass up, giving him a chance to make a hefty salary and re-establish value with a healthy 2020. Whether he gets the opportunity to make that decision is far from certain.

What does Didi bring?
He’s been knighted, his emoji game is strong, he speaks several languages and he’s an artist. That’s all part of the Gregorius experience.

The on-field work has been impressive, too. In his first four seasons with the Yankees, Gregorius combined strong defense with solid baserunning and an above-average bat (104 wRC+), providing production across the board. His 14.7 WAR during that time, per FanGraphs, ranked 33rd among MLB position players and seventh among shortstops.

Gregorius also showed consistent improvement with the bat, raising his home run total, OPS and park-adjusted wRC+ in each of those first four seasons in New York. That culminated in his star-level 2018 campaign, in which he batted .268/.335/.494 (122 wRC+) with 27 homers, 86 RBIs and 4.7 WAR.

If that’s what a healthy Gregorius can offer moving forward, he’s one of the best in the game at his position.

How much should 2019 count against him?
Gregorius, who will turn 30 in February, did not enjoy the ideal platform season heading into free agency. He batted .238/.276/.441, posting the eighth-lowest on-base percentage of anyone with 300-plus plate appearances and generating an 84 wRC+ that was his lowest as a Yankee, also ranking 29th of 36 shortstops (minimum 300 PA). In almost exactly half a season, Gregorius was worth roughly 1 WAR.

The question is whether Gregorius’ injury and lack of a normal offseason and Spring Training had a significant effect on that dropoff. If so, can he reverse course?

The good news for Gregorius is that his power was intact in 2019. He hit 16 homers in 82 games, and Statcast shows that his average exit velocity, hard-hit rate and barrel rate actually increased over ‘18.

The bigger issue was that Gregorius chased more, made contact less, and saw his strikeout rate rise (12.1% to 15.4%) while his walk rate dropped (8.4% to 4.9%). The late start to the season certainly could have played into that, but there is some risk that this was the start of a trend and not a blip.

Is he a Yankee Stadium product?
Looking only at Gregorius’ huge 2018, he produced a .944 OPS and hit 19 home runs at home, compared with .700 and eight on the road. As a left-handed batter who does most of his damage when pulling the ball, Yankee Stadium’s inviting short porch does seem like a good match.

Yet it’s important to remember that there can be a lot of variance in one-season splits. In 2017, Gregorius hit significantly better on the road. The same was true this year, when his road OPS (.840) was higher than his overall mark in ‘18, while his home OPS plunged to .570. Overall since joining the Yankees, Gregorius has batted .255/.302/.441 at home, and .283/.324/.451 on the road. That doesn’t suggest a hitter who can’t succeed outside the Bronx.

Where else could he land?

If the Yankees and Gregorius don’t stay together via the qualifying offer, Gregorius will join a thin group of free-agent shortstops. José Iglesias, Freddy Galvis (if the Reds decline his 2020 club option) and Jordy Mercer would be his most notable competition (though others, including Francisco Lindor, could be available on the trade market).

The flip side is that not many teams have a glaring need at the position. Besides the Yankees, here are five clubs that would make sense for Gregorius, although only a couple have a clear need for a shortstop:

Brewers: They’ll require more offensive depth behind Christian Yelich, especially if Mike Moustakas and/or Yasmani Grandal depart. Shortstop Orlando Arcia is a solid defender but has the third-lowest OPS (.610) of any hitter with at least 750 plate appearances over the past two seasons.

Nationals: Brian Dozier, Howie Kendrick and Asdrúbal Cabrera all will be free agents, so the Nationals will need someone to be Trea Turner’s double-play partner. Depending on what happens with Anthony Rendon and Stephen Strasburg, there could be a lot of money coming off the books.

Padres: It’s time to win in San Diego, and shortstop Fernando Tatis Jr. is a big part of that. Second baseman Luis Urías could be, too, but that isn’t set in stone. Maybe Gregorius fills out a high-profile infield with Manny Machado, Tatis and Eric Hosmer.

Phillies: It’s a team that wants to win and needs to improve. New manager Joe Girardi had Gregorius in New York, and Philly might decide it’s time for a change from César Hernández at second and/or Maikel Franco at third, with Jean Segura installed at short.

Reds: Their offense lagged behind their pitching in 2019, so it could be time for Gregorius to return to his original team. Iglesias will be a free agent, and Galvis might be, too.