Gary Sanchez - Gary Sanchez hit under .200 this season, and played just 89 games. He underwent shoulder surgery in the offseason, hoping this can get that average up next season. Sanchez is expected back before Spring Training, but if any setbacks occur, Sanchez could be looking at more missed time. This would be a big deal despite last season’s subpar play.
Jordan Montgomery - Jordan Montgomery is going to miss most, if not all of the 2019 season, and while New York has the money to go out and land another pitcher, Montgomery is still someone that could be of use as a long reliever or 5th starter in this rotation. He will look to get back on track, as the lefty has shown a lot of promise as an above average starter.
Didi Gregorius - This might throw a wrench into the Yankees plans for next season, as Didi Gregorius is going to miss half the season. This is a big lefty bat out of the middle of the order, and a quality defensive player as well. While we don’t expect anything drastic to happen in the offseason, a major move for Manny Machado would make it interesting when Gregorius does return.
Winning 20+ championships is going to bring some good luck on the injury front, as a lot of their stars had lengthy careers with minimal DL stints. In 2006, Gary Sheffield had torn a ligament in his wrist, and also dislocated it. This was basically the end for Sheffield in New York. In the 2008 season, the Yankees backstop, Jorge Posada had a torn labrum, which caused him to miss the last few months. Posada started to develop more injuries, with a fractured foot later on in 2010.
While Phil Hughes has gone on to pitch elsewhere, his time in New York was filled with injuries, mainly due to his arm. He dealt with fatigue a lot, and eventually had surgery. Rafael Soriano was in the same boat out of the bullpen, but didn’t go on to pitch much later in his career after New York. One of the toughest injuries to see was Mariano Rivera later in his career, as he tore his ACL in May of the 2012 season. Just one day later, starter, Michael Pineda had torn his labrum in his shoulder.
In 2013, Derek Jeter needed ankle surgery, which caused him to miss the first half of the 2013 season. This was also where Mark Teixeira had to have wrist surgery, and Kevin Youkilis had back surgery. The older Yankees were starting to show their durability that season. Jeter would eventually go back on the DL with an injury to the same ankle later that season.