CHICAGO -- The first phase of every offseason is information gathering. The Cubs have spent the past several weeks reorganizing their front office and field staff while also communicating with rival teams and poring over reports and data.

The arrival of the Winter Meetings, which run from Monday through Thursday in San Diego, will give the Cubs a natural spot on the calendar to start shifting into the transactions portion of their offseason timeline. Chicago has made a handful of minor depth additions so far this winter, but the "real change" that Cubs president of baseball operations Theo Epstein has hinted at since the end of last season could be coming soon.

"The important thing is just to keep a really open mind," Epstein told reporters at the General Managers Meetings last month in Arizona, "and be prepared for all different permutations of how things could work out."

Here is a glance at the Cubs' situation as the Winter Meetings loom:

Club needs: Rotation, bullpen and support up the middle

• Rotation: The Cubs could use one more impact starter to lengthen out a rotation that is not getting any younger. Jon Lester, Yu Darvish, Kyle Hendricks and José Quintana currently occupy the first four spots. Chicago could also benefit from adding depth behind the big league staff.

• Bullpen: Craig Kimbrel is under contract to be the closer, but the rest of the bullpen is full of question marks, especially now that multiple veterans -- Steve Cishek, Brandon Kintzler and Pedro Strop among them -- have hit free agency. The Cubs are in the market for an impact arm but also depth options.

• Up the middle: The most logical spots on the diamond to make an upgrade to the lineup are second base and center field. Under the right circumstances, Chicago could target a corner outfielder and shift right fielder Jason Heyward to center.

Whom might they trade? As the Cubs try to balance contending in 2020 with planning for the future, the team must take a close look at the core group that might depart after '21. That list includes Javier Báez, Kris Bryant and Kyle Schwarber, and Willson Contreras will be eligible for free agency after '22. That is the group that could net the most return, but Chicago will also be exploring the possibility of extensions, too.

Someone like Tyler Chatwood, who is owed $13 million in 2020 and could be a candidate for either a rotation or bullpen job, may end up being available in the name of freeing up some payroll. For various reasons (roster fit, performance, contract, etc.), the Cubs could also make Albert Almora Jr., David Bote, Daniel Descalso, Ian Happ, Kimbrel or Quintana available as well.

Prospects to know: It will be fascinating to see how the Cubs handle No. 1 prospect (No. 47 in MLB) Nico Hoerner in 2020, given the impact he had with the big league club late in the '19 campaign. He made the jump from Double-A to the Majors in September and filled in admirably for Báez at short. With second base seemingly up for grabs, Hoerner could make a strong push this spring for an Opening Day job. Or, Chicago might opt to send him to Triple-A Iowa to continue his development.

• Cubs Top 30 prospects

Both Hoerner and catcher Miguel Amaya (No. 2 club prospect) will be in camp with the Cubs this spring. Righty Adbert Alzolay (No. 5) reached The Show in 2019 and could push for a spot on the pitching staff in '20. Hard-throwing lefty Brailyn Marquez (No. 4) and outfielder Brennen Davis (No. 3) impressed on the farm in '19 and will be worth monitoring closely again next summer.

Payroll summary: The Cubs currently have 11 contracts locked in for 2020 at a combined value of $135.1 million. When factoring in projected arbitration salaries, buyouts and the potential cost of the rest of the pre-arbitration-eligible players on the 40-man roster, Chicago's estimated '20 payroll is poised to land in the $190 million range. The Competitive Balance Tax payroll would project to be closer to $200 million, with the first CBT threshold sitting at $208 million. The Cubs went over the first CBT line in '19, but the team has not given any specifics about where its payroll ceiling might exist for '20.

One question: Will the Cubs really make a franchise-altering trade?

So far this offseason, the Cubs brought in a new manager in David Ross, made alterations to the Major League coaching and training staff, and overhauled the leadership hierarchy of the scouting and player development departments. All of the changes have been in the name of changing the culture, modernizing the team's operations and trying to move beyond relying on what worked en route to the 2016 World Series.

The next step very well could be changing the core group that led the Cubs to baseball's mountaintop three years ago. Red flags existed in 2018, but the Cubs won 95 games. Chicago essentially stood pat in '19 and many of the same issues sent the team tumbling to a third-place finish in the division. Epstein has never shied away from making major moves and he is facing a crucial point in the franchise's timeline.