Two of the best players in baseball are set to reach free agency for the first time this winter as New York Yankees outfielder Aaron Judge and Los Angeles Dodgers shortstop Trea Turner will take their tremendous talent to the open market.

Whether those two major market teams are able to retain their stars will be one of the biggest storylines of the upcoming offseason, but they are not the only teams with important free-agency decisions to make this winter.

Ahead we've highlighted each team's most important free agent, based on his production and the void his potential departure would create on the roster. Player options and contract opt-outs were also included in this conversation since those decisions are precursors to a player potentially reaching free agency.

Let's get to it!


American League East

Baltimore Orioles: RHP Jordan Lyles (club option)

The Orioles don't have any major free-agency decisions with veteran Rougned Odor and Robinson Chirinos likely to be cut loose, but they do have a tough call to make on an $11 million club option for Lyles. The 31-year-old has worked a team-leading 156 innings and has a 4.62 ERA and 4.37 FIP on the year. Is his veteran workhorse presence preferable to a $1 million buyout?


Boston Red Sox: SS Xander Bogaerts (opt-out)

The writing is on the wall that Bogaerts is going to exercise the opt-out in his contract and leave the remaining four years and $80 million of his deal on the table. The question now is how aggressively the Red Sox are going to be in trying to keep him around. Nathan Eovaldi and Michael Wacha are also big free-agency calls.


New York Yankees: OF Aaron Judge

There is no question the Yankees would love to keep Judge around, but how far beyond the seven-year, $213.5 million offer he rejected this offseason are they willing to go? He is on his way to a historically good contract year, but his injury history prior to the last two seasons will still be in the back of everyone's mind at the bargaining table.


Tampa Bay Rays: C Mike Zunino

After exploding for a 136 OPS+ and 33 home runs last season, Zunino has battled through a tough contract year. The 31-year-old played in only 36 games before undergoing thoracic outlet surgery, and he was hitting only .148/.195/.304 in 123 plate appearances prior to the injury. Will the tight-fisted Rays be willing to take a buy-low flier on the 2021 All-Star?


Toronto Blue Jays: RHP Ross Stripling

Stripling has been an invaluable swingman for the Blue Jays this season, logging a 3.03 ERA and 1.01 WHIP in 113 innings over 20 starts and eight relief appearances. The 32-year-old is going to get a healthy raise over the $3.8 million he's making this season, and the Blue Jays might have a tough time keeping him around without guaranteeing him a rotation spot.