The Athletic's Jayson Stark reported the Yankees are doing an "extensive" background check on Machado, arguably the crowned jewel of this free-agent class.
Machado, 26, has drawn criticism for his attitude on the field. He was fined for running into Milwaukee Brewers first baseman Jesus Aguilar during Game 4 of the National League Championship Series while running out a grounder. Multiple members of the Brewers called Machado out for being a dirty player.
"I was trying to get over him and hit his foot," Machado told reporters at the time. "If that's dirty, that's dirty. I don't know. Call it what you want."
Machado has also dismissed criticism from those who say he doesn't hustle.
“Obviously I'm not going to change; I'm not the type of player that's going to be 'Johnny Hustle' and run down the line and slide to first base and...you know, whatever can happen. That's just not my personality, that's not my cup of tea, that's not who I am," Machado told The Athletic's Ken Rosenthal.
Didi Gregorius has served as the Yankees shortstop for the last four seasons. He will be a free agent in 2020.
Should the Yankees sign Machado, they would likely look to trade Gregorius. The team has Miguel Andujar at third base and will probably keep him there for the foreseeable future.
Former teammates have gone out of their way to compliment Machado despite his shaky reputation.
"I really like him," a former Orioles teammates told Rosenthal. "He was always a good teammate. Good guy, too—he was great with my kids. Now he did some dumb stuff on the field, but that never truly reflected the guy I know off the field."
Machado had a .297/.367/.538 triple-slash line with 37 home runs and 107 runs batted in last season, splitting time with the Orioles and Dodgers. He and Bryce Harper are expected to sign record-setting contracts this offseason.