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

The Chicago Cubs have made some shrewd business decisions in the last 10 years, and those efforts helped secure four straight playoff appearances and a World Series from 2015-2018. They couldn't have accomplished these feats without bringing in talented players via free agency to supplement their wealth of homegrown stars. These are five of the best free-agent signings by the Cubs in the last ten years.

1. Ben Zobrist

Prior to the 2016 season, the Chicago Cubs inked utility man Ben Zobrist to a four-year contract when he was fresh off winning the World Series with the Kansas City Royals. The deal brought the Cubs a switch-hitting, on-base specialist, while also reuniting Zobrist with his former Tampa Bay Rays manager Joe Maddon. Zobrist primarily started at second base for the Cubs, where he also played in the 2016 All-Star game alongside the rest of the Cubs infield. Down the stretch, Javier Baez began to emerge as a defensive wizard, pushing Zobrist to the outfield. Since Kyle Schwarber was injured the entire year, and there was no DH, Zobrist also saw a lot of time in Left Field in 2016 and the rest of his Cubs tenure.

Although the Illinois native provided good value in 2018 as well, 2016 was the best of his time in Chicago, as he hit 18 bombs and drove in 76 while getting on base at an impressive .386 clip. However, the postseason is where Zobrist shined and he came up with some big hits against the Giants and Indians. The most notable of them was the go-ahead hit in Game 7 of the World Series, where Zobrist shot an opposite-field double to left field to score Albert Almora. That hit not only notched Zobrist the World Series MVP trophy, but a permanent place in Cubs history.

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.

4. Dexter Fowler

This is a double entry, as the Cubs signed Fowler to two one-year deals in 2015 and 2016 respectively. Those wound up being two of the best seasons of Fowler's career, not only from a personal standpoint but for his contributions to the success of the team. The endearing moniker from manager Joe Maddon "You go we go" perfectly summed up the ability for Fowler to set the table while hitting in the 1 spot in the Cubs lineup.

He was instrumental in getting the Cubs on the board early, and this skill showed itself in Game 7 of the World Series with a solo homer off of Cleveland ace Corey Kluber.

5. Jon Lester

The Chicago Cubs decided to employ the services of the 6'4 left-handed workhorse Jon Lester prior to the 2015 season. This 6-year deal worth $155 million was well worth the investment, as Lester made 171 starts and tossed more than 1000 innings in a Cubs uniform. His physical durability and mental determination made Lester a reliable starter for years.

His pitching prowess also came up when it mattered the most, as Lester holds a postseason cumulative ERA of 2.51, and 10 of those starts were for the Cubs. Let's just not talk about his appearance out of the bullpen in Game 7 of the World Series.