The whispers have officially begun for the Chicago Cubs offseason as the regular season has come to an end. The Cubs have fallen short in back-to-back years as in 2018 they blew a lead to the Milwaukee Brewers for the NL Central and lost in the Wild Card round to the Colorado Rockies. Then in 2019, the Cubs let the St. Louis Cardinals and Brewers pull away for the division and final Wild Card spot. After another disappointing season, the Cubs might have to make some changes to stay as strong competitors for the 2020 season.


News broke just before the Cubs final game that Joe Maddon will not be retained as the team’s manager after another disappointing season. Possible candidates for the Cubs could be their bench coach Mark Loretta, first base coach Will Venable, former Cubs Mark DeRosa, and David Ross, John Ferrell, Joe Girardi, and Sam Fuld. Regardless, the Cubs manager position will be the most sought out job in baseball. Maddon will always have a place in Chicago sports history for bringing the World Series back to the North Side.

Nicholas Castellanos

Photo Credit: The Athletic / Sahadev Sharma

This can’t be a debate, the Cubs have to resign Castellanos this offseason. Playing in 51 games for the Cubs, Castellanos batted .321/.356/.646 with 16 HR, 36 RBI, 16 2B, 43 R, 10 BB and 47 SO. Castellanos was one of the steals at the trade deadline and has turned out to be one of the Cubs most consistent hitters. There’s no way you let this man walk, but many teams will be in the fold for Castellanos.


There’s no hiding what was the Achilles heel for the 2019 Cubs. The bullpen was brutal as there weren’t many reliable arms. Some guys are set to hit free agency like Pedro Strop, Steve Cishek, David Phelps (club-option), Brandon Kintzler, and Brian Duensing.

Kintzler seems like the logical guy to bring back due to his 2.68 ERA, but how much will the Cubs being willing to pay a 35 year old pitcher. I believe the Cubs will accept Phelps club-option since it’s only $1M. Duensing is on the way out and I believe either Strop or Cishek will stay. Cishek has the better stats, but seemed to disappear towards the end of the season, but seems like the right decision to bring back. Strop was roughed up all year, which could lead to a lower contract, which could lead to a low-risk high reward for a possible “vintage Strop” or a DFA if Strop’s struggles continue.

In free agency there’s not many huge arms out of the bullpen. The most notable player that comes to mind is San Francisco Giants Will Smith. Smith went 6-0 with 34 saves and a 2.76 ERA. Hector Rondon is a familiar face to the Cubs bullpen. Rondon was 3-2 with the Houston Astros this year and had an ERA of 3.71. Arodys Vizcaino played for the Cubs in 2015, but has been with the Atlanta Braves ever since. Vizcaino was traded to the Seattle Mariners this year in May, but was shut down due to right shoulder problems. In 2018, Vizcaino was solid with 16 saves and an ERA of 2.11, then before the injury he recorded one save and an ERA of 2.25 in four appearances in 2019.


The Cubs have been holding off for a few years on trading their young players, and it might have hurt them since their value isn’t as high as it used to be. Players that could possibly get traded are Addison Russell, Ian Happ, Victor Caratini, and Albert Almora. The allegations towards Russell aren’t the reason why he gets traded; it’s the fact Nico Hoerner is ready to play. Hoerner was an emergency September call-up and thrived with a stat line of .293/.316/.453, 3 HR, 17 RBI, 13 R, 1 2B, 1 3B, 3 BB, and 11 SO. Hoerner could be in line as the Cubs lead-off man that they been desperately needed, who can also field his position well as he committed two errors at SS.

Happ spent most of his time in the minors in 2019 and made his way back to the Cubs, but there are still some things he needs to fix. The potential is still there for Happ and it helps that he can play many positions. The Cubs might need a great offer for Almora to pull the trigger. Almora struggled at the plate this year but has shown to be a .285 plus hitter. The move could be down to have an outfield consist of Kyle Schwarber, Jason Heyward and Nicholas Castellanos. Caratini could be on the way out as well because this might be the best value he has ever had by batting .266 and on-base of .348. Cubs could be looking at a veteran catcher to bring in to replace Caratini. The ideal solution for the Cubs is to get pitchers in return for the bullpen.

The fifth man in the rotation

Cole Hamels is hitting free agency and the Cubs should not consider bringing him back. There’s some solid pitchers in free agency and the Cubs might consider them. Gerrit Cole is the top prize, but a miracle would have to happen for the Cubs to get him and the same goes for pitchers like Madison Bumgarner, Hyun-Jin Ryu and Dallas Keuchel. Realistic pitchers for the Cubs could be Jake Odorizzi, Kyle Gibson, Michael Wacha, Zach Wheeler, Michael Pineda and other players depending on their club-options (Corey Kluber, Martin Perez, and Julio Teheran).

It was another disappointing season for the Chicago Cubs, but depending on what they do in the offseason with selecting a new manager, how they manage free agency and if they decide to make any trades, the disappointments will end sooner than we know it.