The Top 5 Free Agent Signings In Cubs History

After the Cubs big series win over the LA Dodgers yesterday, I was doing my usual check in on Twitter.com to get my daily entertainment reading ignorant tweets from Cubs fans finding anything to complain about. However, since the Cubs won, I knew there wouldn’t be very many Cubs fans bitching so I chose to focus on the tweets which had a positive spin to them.

• One focused on how great Jason Heyward has been this season.
• Another broke down Kyle Schwarber’s swing.
• And the best one I saw set the Cubs recent walk-off win to Pat Benetar’s “We Belong.”

We added Pat Benetar's "We Belong" to the Cubs walk-off celebration last night. This feels necessary. pic.twitter.com/1MeO3OrHzt

— Cubs Insider (@realcubsinsider) June 20, 2018

Although not nearly as entertaining as Pat Benetar, one tweet caught my eye. The tweet stated that yesterday’s winning pitcher, Jon Lester, would go down as the best free agent signing in Cubs history. Now, anytime you say someone will the best to do anything in history, I immediately hesitate because history goes so far back. However, since we were discussing free agency (which has only been around since 1976), my wheels began to turn.

At first I thought, “As great as he’s been, there’s no way Jon Lester could be the greatest Cubs free agent signing in history right?” I mean, the Cubs have signed some pretty great ballplayers in the past forty years that there has to be at least one player better than Lester.

To get some perspective, I jumped in a group text with some of my fellow Cubs brethren and posed the question. Immediately, names began to get thrown out: Derrek Lee, Sammy Sosa, Jake Arrieta, and so on…and so on….and so on. As much as I love those players, I had to remind the squad that we were talking about free agent signings and not trades which drew the response of, “Well shit, I can’t remember who the Cubs signed as free agents.”

So I popped an Old Style and put together my list of who I think are the best free agent signings in Cubs history.

Feel free to fight me if you disagree.

5. Ben Zobrist

On December 9th, 2015, the Cubs signed utility infielder Ben Zobrist to a 4-year, $56 million dollar deal. Zobrist won the World Series in 2015 with the Kansas City Royals and was about as consistent of a baseball player as you would find. The 13-year vet would be brought into Chicago not only for his rock-solid approach to the game, but he’d also serve as a very important presence in a VERY young Cubs clubhouse. His vet moves were front and center early on when he brought his Royals World Series ring into the Cubs clubhouse to give the team a taste of what they would eventually accomplish later on that season.

Zobrist will never receive praise for his offensive numbers (even though they’re pretty damn solid) but he will forever be cemented in Cubs history as the guy who drove in the game winning run in Game 7 of the 2016 World Series. Add to that, he was named MVP of the 2016 World Series and it’s just simply impossible to leave him off this list.

4. Ryan Dempster

I’ll admit, I wanted to leave Dempster off this list simply for the fact that he does one of the worst Harry Caray impersonations ever. Like, it’s literally the worst thing I’ve ever heard. However, as a free agent signing, Dempster put together quite the career on the North Side of Chicago.

The Reds released Dempster after the 2003 season when he had Tommy John surgery. He got knocked around pretty good during his two years in Cincinnati going 8-12 with an ERA north of six but he Cubs took a shot on him the next season when they signed him to a one-year contract. That risky one-year contract turned into nine years as a Cub. Dempster eventually took over the closer job, and in three seasons, he totaled 87 saves. 2008 was the peak of his Cubs career when he returned to the rotation and won 17 games on a team that won back-to-back division titles.

I’d also be remiss if I didn’t mention that I may or may not have added him to this list because he was partially responsible for the Cubs landing Kyle Hendricks as well.

At least I’m honest.

3. Moises Alou

If you can erase the memory of Alou screaming like a baby after the notorious Bartman incident, he was actually a pretty solid free-agent signing. Alou came to the Cubs in December 2001 after helping the Marlins win the World Series four years earlier. The 35-year-old left fielder signed a three-year, $27 million dollar contract with the Cubs and immediately gave all-time Cubs great, Sammy Sosa, some much needed protection in the lineup.

If you erase the 2002 season where he was pretty much hurt the entire year, Alou shined as a Cub. The 2003 team won the NL Central and Alou flourished hitting behind Sosa (.280 with 22 homers, 35 doubles and 91 RBIs.)

He finished 14th in MVP voting in 2004, which usually tends to happen when you smack 39 home runs and collect 106 RBIs. The notorious hand-pisser is definitely an all-time great who unfortunately will only be remembered for flipping out on Steve Bartman.

2. Andre Dawson

I’ll be honest. When I first heard the best free agent in history question, Andre Dawson was the first one to come to mind and I could have sworn up and down that he was the answer to the question. In addition to being one of my top three favorite Cubs in history, he had one of the coolest free agent signing stories in history.

After the 1986 season, the three-time All-Star and 1977 Rookie of the year was desperate to get out of Montreal because the articifial surface was destroying his knees. So Dawson and his agent showed up unannounced at the Cubs’ spring training facility in search of a contract.

The Cubs had already spent a good chunk of change going into the 1987 season but that didn’t stop Dawson’s agent. In a ballsy move, the agent offered the Cubs a blank contract to fill in for what they thought Dawson was worth (or at least what they could afford.)

The Cubs GM filled in $500,000 and got every pennies worth. In 1987, Dawson hit 49 home runs with 137 RBIs and was named the NL Most Valuable Player despite playing on a last-place Cubs team. The future Hall of Famer had one of the greatest melt downs in Cubs history finished his career slashing .285/.327/.507 and to this day is still one of the Cubs all-time greats.

(He also deserves his number to be retired, I’m just saying.)

1. Jon Lester

So as it turns out, the tweet saying that Jon Lester would go down as the greatest free agent signing was correct. When you look at the impact that Lester has had during his time with the Cubs and the role he has played in the clubhouse, there is not another free agent in Cubs history that comes close to what Lester has accomplished.

Lester joined the Cubs on December 10, 2014 when he signed a 6-year, $155 million dollar deal. At that point, the Cubs were on a streak of five straight losing seasons and were in desperate need of an ace for their staff. What became known as the “Jon Lester sweepstakes” turned out to be the biggest free agent signing in Cubs history.

Lester was a dominant left-handed pitcher who had a track record of success. In Boston, he had been lights out in the World Series, where he was  3-0 with a 0.43 ERA in three starts, helping the Red Sox win two championships.

Lester’s first year with the Cubs was up and down but since he became a Cub, he has been the ace everyone thought he would be.

Most starts with 5+ innings and 1 or fewer runs allowed
(2015-present)

48 Jon Lester
48 Jake Arrieta
45 Max Scherzer
44 Zack Greinke
43 Clayton Kershaw
43 Jacob deGrom

— Christopher Kamka (@ckamka) June 20, 2018

Everyone knows the role he played in Game 7 of the World Series when he came in as a relief pitcher to help the Cubs win their first championship in over a century but like Zobrist, who I’ve mentioned earlier, people underestimate the role he played in changing the entire culture of the Chicago Cubs.

Yes, Theo Epstein was a huge part of the culture shift away from the “lovable losers” but you have to have your key guys buy into that philosophy as well. Lester just signed a $155 million dollar contract, he didn’t have to buy into shit if he didn’t want to because the man would be getting paid regardless but that’s not the type of guy Lester is. He is a true blue-collar workhorse who shows up to work each day, doesn’t complain, and is the leader by example that every team needs.

Now that he’s officially halfway through his contract, Lester is still dealing. As of today, he’s 9-2 with a measly 2.10 ERA and is all but confirmed to land a spot on this year’s All-Star team. He currently ranks in the top five in the NL in wins, WAR, WHIP, and ERA and is poised to put up his best season as a Chicago Cub.

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All five of these free agents changed the history of the Chicago Cubs but when you look at the impact left on the organization, Jon Lester takes the cake. He will undoubtedly go down in Cubs history as one of the greatest left handed pitchers in team history and I hope his resurgence this year will result in another Cubs run at a World Series championship.