The Cubs piled up the wins last summer only to have the rug pulled out from under them in the fall. The lineup struggled over the final two months, injuries hindered the roster and Chicago not only lost its grip on the National League Central crown but was bounced by the Rockies in the NL Wild Card Game.
With that as the backdrop for this critical offseason on the North Side, the team's decision-makers have stressed the importance of improvement from within for 2019. Cubs president of baseball operations Theo Epstein called the year ahead a "reckoning" for an organization trying to capture another World Series crown. And, with the bitter taste of last season's ending still lingering, the club wants to get started.
"We certainly weren't who we believe we can be," Cubs general manager Jed Hoyer said earlier this month. "And I know that this group of players has another gear that it can get to that we didn't get last year. We've spent a lot of time talking about how to get there. So, the sooner we can start playing games again, the better. I can't wait to drive to Arizona. It'll be great."
There are still several weeks remaining before Spring Training begins and -- with the exception of signing veteran utility man Daniel Descalso -- the Cubs have been quiet to date this offseason. There are still objectives to tackle and plans to formulate in preparation for the spring ahead and season to follow.
Here are some items left on the Cubs' to-do list for the rest of the offseason:
1. Address the offense
As has been well-documented throughout the winter, the Cubs do not appear to have much financial wiggle room. As things currently stand, the team's payroll projects to be north of $200 million, putting Chicago in a position where trading contracts in place would probably be required in order to add any contracts of significance. So, as much as Cubs fans may have wanted a blockbuster free-agent addition this winter, that looks unrealistic.
Still, what Chicago's offense went through down the stretch in 2018 should not be ignored or left unaddressed. The team posted a .249/.316/.389 slash line in the second half and posted the Majors' highest ground-ball rate (47.8 percent) over the final two months. Descalso adds a disciple of the air-ball revolution to the equation, but that alone will not right what went wrong.

2. Get Kristopher Bryant healthy
This will be crucial for the Cubs. A left shoulder injury sapped Bryant's slugging percentage last season, but the good news of late has been that the third baseman has been unrestricted and feeling great in his winter workouts. If Chicago does not have the financial wherewithal to add a premier hitter to the mix, it absolutely needs Bryant to report to Spring Training healthy and back to his old offensive ways. The Cubs will also be counting on continued development from the likes of Kyle Schwarber and Ian Happ, and strong comeback campaigns from Willson Contreras and Albert Almora Jr.
3. Add bullpen depth
This will be especially important for the first month of the season. Brandon Morrow's status will become clearer as Spring Training progresses, but the righty may need to open the season on the disabled list after undergoing a debridement procedure on his throwing elbow in November. Given their financial situation, the Cubs might not be able to reel in one of this offseason's marquee relief arms. Instead, expect Chicago to see how the market develops and then target some value and depth options as spring approaches.

4. Sort out the middle-infield puzzle
The Cubs and Major League Baseball continue to keep a close eye on Addison Russell's progress behind the scenes as he works through a treatment plan related to his violation of MLB's Joint Domestic Violence, Sexual Assault and Child Abuse Policy. Russell was tendered a non-guaranteed contract and will be ineligible until May 3 while finishing out a 40-game suspension. The current plan calls for Javier Baez to handle shortstop, leaving a hole at second. Descalso can help at that spot, along with internal options like Benjamin Zobrist, David Bote and Happ.
5. Determine roles for Mike Montgomery and Tyler Chatwood
When the Cubs picked up Cole Hamels' $20 million team option, that essentially locked the five-man rotation into place. Hamels will be on the staff, alongside Jonathan Lester, Kyle Hendricks, Jose Quintana and Yu Darvish. If Darvish's comeback from right elbow and triceps issues lingers into April, the Hamels deal offers solid depth. If the entire rotation is healthy and no trades are made between now and the spring, then the Cubs need to map out the best way to utilize Montgomery (eligible for arbitration) and Chatwood (set to earn $12.5 million in '19).