Notable Cleveland Indians Winter Meeting moves since 2010

The Indians have made three trades during the Winter Meetings over the course of the last decade, all of which wound up significant.
2014
During the 2014 meetings, the Indians traded for a veteran bat as they added Brandon Moss from the Oakland Athletics in exchange for infield prospect Joey Wendle.
Moss was coming off a 2014 season that saw him earn All-Star honors as he slugged 25 home runs and picked up 81 RBI’s for the A’s. He was unable to replicate that success in Cleveland as he hit just .217 with 15 home runs in 94 games for the Tribe before being traded at the 2015 July Trade Deadline to the St. Louis Cardinals.
Wendle spent short stints with the A’s in both 2016 and 2017 before landing with the Tampa Bay Rays, where in 2018, he finished as an AL Rookie of the Year finalist after slashing .300/.354/.435 with 61 RBI’s.
He helped guide Tampa to the World Series in 2020 after hitting .286 in 50 games for the AL champion Rays.
2017
In 2017, the Indians made a seemingly small move when they dealt right-handed reliever Shawn Armstrong to the Seattle Mariners for International Bonus Slot Money.
Armstrong pitched to a 4.38 ERA in 21 relief appearances to the Indians in 2016 and was clearly simply a depth piece in the pen.
Since leaving Cleveland, however, Armstrong has found success. In 2017 he posted a 1.23 ERA in 14 appearances for Seattle and in 2020, he posted a 1.80 ERA in 14 relief outings for the Baltimore Orioles.
2018
Perhaps the most memorable Winter Meetings trade made by the Indians in the past 10-years was a three-team deal with the Mariners and Rays in 2018.
The Indians sent slugger Edwin Encarnacion to Seattle and both infielder Yandy Diaz and right-handed pitcher Cole Sulser to the Rays in exchange for first basemen Carlos Santana bringing him back to Cleveland after one-year away and young first basemen Jake Bauers from Cleveland.
Encarnacion spent just two full months in Seattle before being traded to the New York Yankees; Diaz emerged as a key contributor to the Rays 2019 AL Wild Card Game-winning team hitting two solo home runs for Tampa in their win over Oakland and then helped the team reach the World Series in 2020 and Sulser wound up landing in Baltimore where he became the Orioles closer in 2020.
As for Cleveland’s addition, Santana put together an All-Star 2019 season that saw him hit .281 with 34 home runs and 93 RBI’s but struggled in 2020 and is now a free agent while Bauers slumped through the 2019 season and spent all of 2020 at the Indians alternate site in Lake County.