Ranking the 5 best Chicago Cubs free agent signings of the last decade

Los Angeles Dodgers v Chicago Cubs
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David Ross
World Series - Chicago Cubs v Cleveland Indians - Game Seven / Ezra Shaw/GettyImages

3. David Ross

I like to think of David Ross as the glue that held together the 2015-2016 Cubs. When the Cubs signed Jon Lester prior to 2015, his personal catcher David Ross was part of the deal, as he decided to spend his last two seasons with his former Red Sox battery mate. But Ross became much more than Lester's catcher, as the 38-year-old soon went by the affectionate moniker Grandpa Rossy. He brought honest accountability to the dugout and helped a roster of veterans and young players realize their potential. These leadership qualities were enough for the Cubs front office to position Ross as their next manager after Joe Maddon's contract expired in 2019.

Ross did some amazing things in a Cubs uniform, including catching a no-hitter and hitting a home run in Game 7 of the World Series at 39 years old. He continues to lead the club as he heads into his fourth season as manager, where he will hopefully have the tools to bring them back to the playoffs for the first time since 2020.