Five Things the Chicago Cubs Should Do to Stay Relevant

by Mohammad Samra / Staff Reporter

Wrigley Field’s iconic marquee with the message ‘World Series Champions’ after the Cubs won their first World Series in 108 years in 2016. Photo by Mohammad Samra

This year, the Chicago Cubs missed the playoffs for the first time since 2015 after a late September meltdown left them out of a Wild Card spot. Chicago’s steady decline since winning the World Series in 2016—their first in 108 years—has put the brakes on what could have been a dynasty. 

The Cubs’ front office has made it clear that they are not satisfied with the direction the team is heading and have already promised changes, starting with the firing of manager Joe Maddon. 

The 2020 season will be a pivotal one for Chicago. It’s still way too early to predict where they will finish, but here are five things the Cubs should do this offseason if they want to stay relevant in the Windy City.

1.) Avoid long-term, big-money contracts.

The Cubs are notorious for signing players to pricey, long-term contracts. They currently have three players—Jason Heyward, Jon Lester and Yu Darvish—who are signed for at least six years and $100 million. 2020 has a couple of free agents such as Gerrit Cole and Anthony Rendon, who will both likely get $100 million deals, but they don’t fit the Cubs’ needs. The biggest temptation for the team will be signing core players such as Javier Baez and Anthony Rizzo to long-term mega-deals, which will restrict what they can do in upcoming years in free agency, forcing them to address their concerns through trades. Draft and develop relievers.

2.) Draft and develop relievers.

It’s no secret that the bullpen has always been a weakness for the Cubs. From Spring Training to the World Series, the bullpen consistently finds a way to blow leads, and there never seems to be a definitive solution. Free agent relievers in the past have been disastrous. Brandon Morrow is always on the injured list, Craig Kimbrel has been a trainwreck, Wade Davis lost some momentum near the end of his 2017 stint and flamethrower Aroldis Chapman almost cost them Game 7 of the 2016 World Series. Chicago should focus on drafting relievers who can develop into reliable middle-inning pitchers.  

3.) Invest in a leadoff hitter.

Chicago hasn’t had an elite leadoff hitter since Dexter Fowler in 2016. The absence of a credible leadoff hitter might seem minor at first, but the identity of the offense has changed without someone who can consistently be at the top of the lineup. The Cubs quickly became a hit-or-miss team offensively without one. In 2019, Cubs players combined for 256 home runs, the most in franchise history, yet they ultimately finished third in their division because of their inability to consistently score runs. The most obvious solution is Kansas City Royals second baseman Whit Merrifield. Merrifield has three years left on a super team-friendly deal, and he led the league with 206 hits this season. The Cubs should be willing to give up role players like Albert Almora Jr. and Ian Happ to get him. 

4.) Rebuild the farm system.

A majority of players from the 2016 championship team were players who spent time in Chicago’s developmental system. The Cubs have spent four years in “win-now” mode and have given up early on star prospects such as Gleyber Torres and Eloy Jimenez. Nico Hoerner’s recent stint with the team proves that they at least have some talent brewing in the minors, but if they want to extend their fragile championship window beyond 2022, when most of the team’s core become free agents, they need to start thinking long term. 

5.) Trade Kris Bryant.

Do you remember when the Cubs kept third baseman Kris Bryant in the minors for two weeks to start the 2015 season just so they could gain an extra year of club control over him? With that extra year, Bryant became an extremely appealing trade target for teams looking to bolster their lineup without having to immediately break the bank. Sure, trading Bryant is a risky move, but he rejected a $200 million contract extension in 2018, meaning that he is more than likely leaving after his current contract expires in 2021. Bryant is also compiling a lengthy injury history which can prove to be concerning, assuming his next contract lasts well into his 30s. He had a solid 2019 season, hitting 31 home runs and batting .282. Trading him while his stock is high and adding some much needed depth to either the bullpen or the farm system instead of potentially wasting the next two years and gaining nothing from him walking away might just be the right call at the moment. Chicago still has the talent to make the playoffs every year, but they should also prioritize staying playoff contenders before they stumble into another 108-year championship drought.

Categories: Recent Posts, Sports


4 replies

  1. Bryant should be traded, but not yet. IMHO, Contreras is the first trade piece. he’s injury prone, can’t frame pitchers. He has an arm, and can hit. Caritini can hit, can frame, arm average, but that’s enough. You can get value for Contreras. Let’s see if Bryant can rebound. If he has a good year, trade before his walk year.

  2. Need some pieces? Yes, it appears they do. I really like what they have now and think that with the change in the managerial spot it will be a difference maker. Clean up sloppy play( base runnin’, situational hitting, a bit better defence, show some fire out there). Lester ain’t done yet, Darvish is showing he may be worth the $$$, Hendrick

  3. New leadership will make a difference if players give it a chance and are willing to follow. Depending on who isn’t there by there own choice, I believe, is going to be the factor in who and if a trade is needed right now. So much talent here. They seem to get along and some time off is going to help. These guys played a bunch of games with very little time off at the end of 2018 and I think think that was the start of this hiccup, along with some acquisitions that didn’t work out, it happens! This team as it stands can and will win if given the opportunity. Big time changes aren’t necessary until into next season if the ship hasn’t been righted. But have to keep Castellanos, Happ and Bote are keepers, Zobrist is very valuable in many ways, young pitchers have done pretty good and have strong upside. A lot of positives here, don’t give up on this team just yet. Yes some changes, but let’s not go overboatd, have faith in your team, your Chicago CUBS. Cubs win!!, Cubs win!!

  4. Chicago can get a lot more in return if they trade Bryant with two years of club control compared to one. That provides some type of stability for any team looking to either extend or open up a championship window. Also, Braynt is coming off of a solid season, and I believe it’s too risky to allow him to suffer a potential injury or have his offensive numbers regress, as that would severely diminish his trade value. Contreras is far from an elite catcher, but he’s projected to make $4.5 million next year compared to Bryant’s $18.5 million, according to Bleacher Nation. That makes him a relatively cheap option over the next couple of years while Caritini expands his game. Moving Bryant this offseason would greatly benefit the future of this team. It might not be the most popular move, but it’d certainly give the Cubs an extended playoff window. They don’t need to be the best team in the league every year to make a run at a World Series ring. The Dodgers won 106 games this season and were a first round exit.

    I appreciate your input! If you’d like to further discuss baseball or any other sport feel free to e-mail me at or

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