That could become a necessity because of the organization's shortcomings after a disappointing 84-78 season. The Cubs farm system has shown turtle-like progression in the player development department in recent seasons. That leaves two paths to acquiring new talent: the free agency and trade markets.
While the Cubs have some significant money coming off the books with left-hander Cole Hamels, utilityman Ben Zobrist, reliever Brandon Kintzler, reliever Steve Cishek and reliever Pedro Strop becoming free agents, the trade market figures to play a piece in addressing their needs as well.
The current group's window of contention spans two more years -- through 2021. First baseman Anthony Rizzo, third baseman Kris Bryant, shortstop Javier Baez and outfielder Kyle Schwarber are set to become free agents after the 2021 season. Going back as far as 2015, the Cubs front office has tried to entice those four and catcher Willson Contreras to sign long-term extensions. It's been to no avail, for various reasons.
In Rizzo's case, the seven-year, $41-million deal with two club options tacked on the end that he signed in May 2013 has been a blessing for the team and also could be a curse in the Cubs' quest to sign him to another extension. Rizzo has been a star and become a Cubs icon on a bargain deal. Because of that, his representation wants to maximize his value of his next contract, and the open market is the best path toward doing that.
The same can be said for the other members of the Cubs' core. None of them want to get shorted on future payouts, so it could be hard to sign them to extensions.
The Cubs don't want them to walk for nothing and also want to replenish their farm system, which is why they must consider all trade options that are promising.
"We have had a group that has accomplished great things," president of baseball operations Theo Epstein said in his end-of-season press conference. "We went to the playoffs four straight times and averaged 95 wins. If you want to say we were stubborn with this group, I think that is fair. We had a real belief in this group. This reveals real change is needed and repair. I think there are a lot of players that are in this group that will be a part of the next championship team."
But who won't be? That question looms large over the offseason.
The Cubs need an infusion of young pitching to contribute to the next wave of contention, as they've been abysmal at developing homegrown arms in the Epstein era. Much of the trade speculation centers around the 27-year-old Bryant, in part because of what his supreme talent could bring in return and in part because of the belief across the league is that he will enter free agency after the 2021 and demand a mega-deal. Bryant also has the ability to play the outfield well, opening up more trade possibilities, but trading him would be painful for the organization.
Epstein has indicated there are no untouchables on the Cubs.
"Next year is a priority, but we have to balance that with the long-term and developing a new one," Epstein said. "We are now just two years away from some of our best players reaching the end of the club's contract control with the Cubs."
When assessing the Cubs' organizational depth and strength, the most logical candidate to be traded seems to be the 27-year-old Contreras. Backup catcher Victor Caratini has been a solid fill-in when Contreras has been hurt. Caratini hit .266 with a .794 in 95 games in 2019. Beyond him, the Cubs' No. 2 prospect is 20-year-old catcher Miguel Amaya, who hit .235 with 11 homers, 57 RBIs and a .753 OPS in 99 games at advanced Class-A Myrtle Beach this past season. He also plays solid defense. The belief is Amaya needs a full season at Double-A before matriculating to the big leagues.
Baez, who turns 27 in December, would be the most difficult player to replace. He has turned into one of the most complete players in the game, and shortstop is a difficult position to fill with an elite all-around player.
The Cubs have been rewarded for their faith in Schwarber, who turns 27 in March. He posted career-best marks in hitting .250 with 38 homers, 92 homers and an .871 OPS this past season. Schwarber could be better suited to age as a designated hitter in the American League, and the Cubs could probably deal him for a solid contributor in another area of need.
It's hard to envision the Cubs trading Rizzo, who has been the face of the franchise since 2012. At 30, he wouldn't fetch as much as most of the others on the trade market, and he's in the back end of his prime. Rizzo has meant so much to the organization with his persona, production and off-the-field charity work in the community.