When the Chicago Cubs captured their first World Series title in 108 years in 2016, it seemed as though they were on the precipice of a potential dynasty.
With young players like Kris Bryant, Javier Baez, Anthony Rizzo and Willson Contreras in place, as well as one of the best starting rotations in baseball, the Cubs were primed for a run of unprecedented success.
However, the last three years have been increasingly frustrating for the North Siders.
The Cubs reached the NLCS in 2017, but they were dominated by the Los Angeles Dodgers. After jumping out to a hot start in 2018, a September collapse led to Chicago losing its grip on the NL Central. They were defeated in the Wild Card Game in stunning fashion.
In 2019, the wheels came off. Despite some good individual performances from the likes of Bryant, Rizzo, Baez, Kyle Schwarber and a resurgent Yu Darvish, the Cubs were plagued by a lack of bullpen consistency and inopportune hitting. They missed the playoffs for the first time since 2014, resulting in the end of the Joe Maddon era.
The Cubs have already made a number of organizational changes this offseason, most notably hiring former backup catcher David Ross to be the new manager. But the most consequential moves will be made this winter.
Chicago has a number of bullpen arms entering free agency, and Nicholas Castellanos hits the open market after a sensational stint with the club. Theo Epstein is likely to be strapped for cash yet again throughout the offseason, but there are tangible upgrades to be made.
Here are three ideal free agency targets for the Chicago Cubs.
3. Howie Kendrick
Kendrick did wonders for his stock with a remarkable postseason.
The veteran infielder slashed .286/.328/.444 with 12 RBI, but his performance was most notable because of the plethora of clutch hits he delivered. Kendrick clubbed a game-winning grand slam during Game 5 of the NLDS, then hit a go-ahead two-run homer to clinch Game 7 of the World Series for the Washington Nationals.
Other competitors such as the Tampa Bay Rays have shown interest in Kendrick, but the Cubs should pounce. Chicago has a definite need at second base. They ranked 25th in WAR at the position, and Ben Zobrist is a free agent. While a reunion with Zobrist could also make sense, Kendrick might be the better option.
Kendrick slashed .344/.395/.572 during the regular season, and he is a career .294 hitter. For a homer-dependent team like the Cubs (who ranked last in contact percentage), he would be a vital addition to the lineup.
2. Will Harris
Harris is the prototypical bullpen pitcher Epstein looks for in free agency: veteran, disciplined and likely affordable on a short-term deal.
The right-hander had a rough conclusion to his 2019 campaign, but he paced the Astros in bullpen ERA (1.50) and all of his pitches have tremendous movement. Harris was also dominant during the 2019 postseason prior to Game 6 of the World Series, and the Astros likely would not have made it out of the ALCS without Harris in the bullpen.
Meanwhile, the Cubs need to go out and add pieces. They declined team options on a number of arms, and Pedro Strop, Brandon Kintzler and Steve Cishek are all free agents. Youngsters like Rowan Wick and Brad Wieck showed promise in September, but the Cubs clearly need quality arms in relief.
Harris should be one of the most coveted relievers on the market. However, the Cubs need to fortify the middle innings, and Harris could also move into the closer role if Craig Kimbrel continues to struggle.
Teammate Joe Smith could also be an option for Chicago, but they should do all they can to sign Harris.
1. Zack Wheeler
This is a bit of a departure.
One might expect a big-market team like the Cubs to pursue Gerrit Cole or Stephen Strasburg. However, even if they create more payroll space through a series of trades, they probably cannot afford either of the top two pitchers on the market.
But what about Wheeler?
The 29-year-old is coming off another season with a sub-4.00 ERA, and his peripherals suggest that he has been even better than the numbers.
Chicago needs help in the rotation with Cole Hamels hitting free agency and Jon Lester in the twilight of his career. If they are able to flip Jose Quintana to create space, Wheeler would be an immediate upgrade in a rotation that needs power arms alongside Yu Darvish.
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