Chicago Cubs: Key free agent moves since 2016

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Free agency has gone from fun and exciting to frustrating and uneventful for Chicago Cubs fans since the franchise opened a new era five years ago.

After the unexpected run to the NLCS in 2015, the Chicago Cubs were ready to go for all the marbles in 2016. Before 2015 the team had landed Jon Lester on a six-year deal, a key move in their rise to success. Going into 2016 the Cubs put themselves back and the map and looked to attract some of the big names on the free agent board.

After winning it all in 2016 the Cubs attempted to continue to plug some holes on the roster with more signings in 2017-2018. The past two offseasons had a few smaller signings, but to the frustration of fans, no big names. This article is going to look back and evaluate the key free agent signings the Cubs have made since the 2015-2016 offseason.

Criteria for this article: Key MLB-deal free agent signings only. No minor league deals, trades, Rule 5, etc. These signings being evaluated were meant to make an immediate impact with the big league club in some form. It would be hard to look through every signing so we are sticking to the biggest ones possible. Each signing will get a “current” grade if they are still on the team or “final” grade if they have since moved on or retired.

Chicago Cubs: They spent big bucks to land the guys they wanted in Free Agency before the World Series season.

John Lackey

Expectation: A durable veteran starter with solid command that could anchor the middle of the rotation who was coming off a fantastic year in St. Louis (2.77 ERA, 1.2 WHIP in 33 starts). Lackey had a reputation for being a force in the postseason.

Reality: In the 2016 regular season, he lived up to expectations. He pitched to a 3.35 ERA and 1.1 WHIP in 29 starts. His postseason was not great, but it did not hurt them in the end. His final season in 2017 was not very good, pitching to a 4.59 ERA (5.30 FIP) in 31 games. His final moments as a Cub included Justin Turner hitting a walk-off homer off him in the NLCS that year. In the end he did not get a haircut, but got jewelry and that was enough.

Final Grade: C+

Ben Zobrist

Expectation: A super-utility man who is both a professional teammate and hitter. Zobrist played many years for Joe Maddon in Tampa, was an All-Star twice (2009, 2013) and a World Series champion with the Royals in 2015. The Cubs won the Zobrist sweepstakes over the Mets and got him on a four-year deal.

Reality: Everything and more. Hit .269/.362/.411 as a Cub, made his third All-Star team in 2016 and was the 2016 World Series MVP. What more can you say?

Final Grade: A

Jason Heyward

Expectation: The once highly-touted Atlanta Braves prospect had a fantastic year in 2015 with the Cardinals, hitting .293/.359/.439 and winning his third Gold Glove at age 25. Cubs gave Heyward a massive $184 million deal hoping to get the very best of him as he was hitting his prime age.

Reality: Not quite what the fans had hoped, though not as awful as some might try to make it out to be. No question his 2016 regular season was awful, hitting just .230/.306/.325 in 142 games, but he won another Gold Glove and made the great “rain delay speech” in the World Series.

Since 2017 he has continued to be a Gold Glove-caliber defender and has hit .260/.335/.406 with 40 homers in 400 games. Not $20+ million a year good, but those numbers are slightly above average. He is a solid ballplayer who has done some good things for the team even if being a bit overpaid.

Current Grade: B-

Dexter Fowler

Expectation: The guy who had a .346 OBP and hit 17 homers for the Cubs in 2015 was heading to Baltimore.

Reality: SURPRISE! He came back on a one-year deal, had a career-high .393 OBP in the regular season, made the All-Star team and hit a leadoff homer in Game 7 of the World Series. You go, we go…to the World Series victory parade!

Final Grade: A

Chicago Cubs: Not nearly as much money spent, but still a few smaller moves to fill some holes on the defending champs.

Jon Jay

Expectation: A veteran slap-hitting platoon/bench bat that can play solid defense in the outfield and can put up a nice batting average. Chicago Cubs fans were very familiar with him in his six years with the Cardinals.

Reality: Jay gave the Cubs exactly what was expected of him. He hit .296/.374/.375 in 141 games and switched between left and center. That .374 OBP was a career-high for him. His leadoff double to start Game 5 of the NLDS helped get the Cubs their first run, and they needed every one they got in that game.

Final Grade: B+

Koji Uehara

Expectation: A reliable piece that could pitch in the back end of the bullpen and miss bats. Uehara had a tremendous run in the majors since coming over from Japan. He was an All Star in Boston and recorded 79 saves in four years as a member of the Red Sox. After trading for stud closer Wade Davis, the Cubs further improved their bullpen.

Reality: At age 42 he overall did fine. Despite some rocky moments he still put up a 3.98 ERA, 3.79 FIP, and 10.5 K/9 in 43 innings. Not like his prime years in Boston where he accumulated a 2.19 ERA, but for a 42-year-old? Not bad.

Final Grade: B

Brett Anderson

Expectation: If healthy and all going well, a fifth starter who could fill in the hole at the bottom of the rotation. His career had seen stretches of potential, mainly with Oakland, but often derailed by numerous injuries. Still, he had shown enough promise in his career to merit a try.

Reality: An 8.18 ERA and 2.1 WHIP in six starts leading to a very short tenure in Chicago. The Cubs took a gamble and it just did not work.

Final Grade: F

(Photo by Victor Decolongon/Getty Images) /

Chicago Cubs: They opened the pocket books again for the 2018 season and it got mixed results.

Tyler Chatwood

Expectation: Finding a solidified arm to fill the bottom of the rotation with the ability to get plenty of groundballs with the movement on his pitches. Cubs hoped that getting Chatwood away form Coors Field would help him reach the potential with the stuff he has, and they paid him $38 million.

Reality: Season one was an absolute disaster. The stuff he threw had good velocity and all sorts of wicked movement…but the pitchers were never close the zone. Chatwood pitched to a 5.30 ERA and an abysmal 8.2 BB/9. He was the leader in all of baseball in walks (95) in just 103 2/3 innings. In year two as a long reliever/spot starter, to his credit, he improved a bit as he put up a 3.76 ERA in 38 appearances. If he can throw strikes, he can be effective.

Current Grade: D

Brandon Morrow

Expectations: The veteran pitcher signed a two-year, $21 million to fill the role as Cubs closer. With the Los Angeles Dodgers in 2017, he pitched to a 2.06 ERA, 0.92 WHIP and 1.55 FIP in 45 games.

Reality: He was dang good when he pitched in the first half of 2018, putting up a 1.47 ERA, 2.96 FIP and recording 22 saves in 30 2/3 innings. Then he got hurt and has not pitched since. The Cubs bought out his contract and brought him back on a minor league deal, so while technically still a Cub, it is doubtful he pitches here again.

Hate to give him a harsh grade because his pitching was very good and injuries are freak accidents, the signing itself did not work in the long run with all the unfortunate setbacks.

Current/Final? Grade: D

Yu Darvish

Expectations: The big move. A man who since coming over from Japan in 2012 was a four-time All-Star and all-time leader in K/9 was brought in on a $126 million deal to be the next ace of the staff. In his first 131 starts he had over 1,000 strikeouts before joining the Chicago Cubs.

Reality: The grade overall looks meh now, but there is plenty of reason to believe it will improve. His first season was a disaster as he pitched in only eight games, posting to a 4.95 ERA, before getting hurt and missing the rest of the year. In 2019 he started off rocky again but then got his confidence and mojo back.

From July-September we saw the Darvish that we had been waiting for as he put up a 2.95 ERA and 124 strikeouts vs. seven walks in 14 starts. After an awful start to his Cubs tenure, things are looking to keep going up for him. We know how talented his.

Current Grade: C

Steve Cishek

Expectations: A reliable back-end bullpen piece that can either come in the seventh, eighth or ninth inning. Another experienced reliever, Cishek was a guy who entered 2018 with a career 2.73 ERA and 121 saves when he inked a two-year deal with the Cubs.

Reality: In his two years, he did the job he was supposed to. Over 2018-2019 he pitched to a 2.55 ERA, 1.12 WHIP and 3.97 FIP in 150 games. He was worked like a dog and did struggle toward the end of both seasons with, but he came up big on a number of occasion out of the pen and helped put out some fires.

Final Grade: B

Craik Kimbrel / Chicago Cubs (Photo by Rich Schultz/Getty Images) /

Chicago Cubs: The biggest free agent signing was in the regular season, and there was not much around that.

Daniel Descalso

Expectations: To be a veteran utility/depth guy to play reliable defense and come off the bench. The fans wanted another lefty bat in Bryce Harper, but that did not happen. Another familiar face to Cubs fans as he spent many years in St. Louis.

Reality: Woof. After a solid first few weeks, Descalso suffered an ankle injury and his season was derailed completely. He finished the 2019 season hitting a career low .173 in 82 games with only eight extra-base hits. Descalso was never Ted Williams as a hitter, but no doubt 2019 was far and away his worst season as an MLB player.

Current Grade: F

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Brad Brach

Expectations: An experienced bullpen arm that can miss bats and be relied on to appear in 60+ games. Brach came to Chicago with a career 3.08 ERA and 9.5 K/9 in 456 innings. An All Star in 2016 with the Orioles, Brach had an overall good resume outside some command issues.

Reality: In 43 appearances as a Cub he walked 31 batters and pitched to a 6.13 ERA before being released. The Mets picked him up and he in 16 games pitched more effectively (3.68 ERA and 2.67 FIP). Just did not work out for the Cubs.

Final Grade: F

Craig Kimbrel

Expectations: The Cubs got a closer, a real closer…the best closer the past decade. Obviously this move was made mid-season when Kimbrel waited out the offseason to be signed. In July, 2019 the two sides agreed to a 3-year, $43 million deal. Kimbrel is a seven-time All Star and is the save-leader among active relievers.

Reality: His first stint as a Cub was an utter mess. Blowing three of 13 saves does not seem all that bad, but the numbers are ugly. 6.53 ERA, 1.597 WHIP and 8.00 FIP in 23 games. In just that span he gave up a career-high nine home runs. Kimbrel’s struggles can likely be attributed to not only having to come in mid-season but also injury issues he had as well. Still giving him the benefit of the doubt moving forward having such an incredible resume, but so far it has been not good at all.

Final Grade: D-

Next. World Baseball Classic Postponed. dark

The last few years have been pretty brutal for the Chicago Cubs in free agency. Not only making few big moves, but seeing them mostly not work out for various reasons. There is potential for some of them who are still on the team to rebound but some of the ones that did not work are already gone. Curious to see what happens this coming winter.

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Chicago Cubs: Key free agent moves since 2016 – expectation vs. reality