As the top shortstop on the free agent market, Didi Gregorius had been widely tabbed as a candidate for a multi-year deal, even in the wake of his injury-shortened 2019 season. While multiple teams have indeed shown interest in Gregorius this offseason, he and his agents are also considering the possibility of accepting a one-year offer, The Athletic’s Ken Rosenthal reports (subscription required).

There would certainly be risk in such a maneuver, though Rosenthal notes it would be a “bet on himself” move from Gregorius in the hopes of guaranteeing himself a larger multi-year deal next winter than he would this offseason. Even in the short term, it could lock in more money for Gregorius over two seasons than he would over a hypothetical three-year contract.

For example, let’s take the three-year, $42MM that MLB Trade Rumors projected Gregorius would receive on the open market. That works out to $14MM in average annual value, and there’s surely enough interest in Gregorius (especially on a one-year pact) that he would easily surpass $14MM for 2020, and likely get more than the $17.8MM value of this winter’s qualifying offers. So let’s say Gregorius signs for $18MM in 2020, and then delivers a performance akin to his 2017 (4.1 fWAR) or 2018 (4.7 fWAR) seasons with the Yankees. Such a year would surely put Gregorius in line for a qualifying offer from his new team next winter, which would land in the ballpark of $17.8MM. In a worst-case scenario, Gregorius could just accept the QO if he still didn’t like his chances in free agency, giving him roughly $35.8MM over the 2020-21 seasons — a hefty bump up from the $28MM he’d have in the same span if he accepted our predicted three-year pact.

As Rosenthal notes, the 2021-22 offseason could be heavy with star shortstops available in free agency, as Francisco Lindor, Javier Baez, Carlos Correa, and Corey Seager are all scheduled to hit the open market. That would seemingly make it unlikely that Gregorius takes a two-year deal this winter, as he would be a 32-year-old shortstop competing for free agent dollars against all those younger stars. A contract offer of four or more years, meanwhile, doesn’t seem to be too realistic, as even the teams most interested in Gregorius would probably balk at guaranteeing four years to a player coming off such a lackluster platform season.

The counter to accepting a one-year deal, of course, is that Gregorius might desire long-term security after facing such a serious injury like the Tommy John surgery that sidelined him for a large chunk of 2019. Given that we’ve already seen some rather surprisingly high figures on the free agent market thus far, Gregorius could also benefit beyond our $42MM projection. The Phillies, Brewers, and Reds have already been linked to Gregorius, and it’s possible more teams could enter the fray depending on other trades, signings, or injuries.