Here’s a Handy Checklist of Cubs Rumors to Follow During Winter Meetings

The upcoming Winter Meetings have potential to be transformative for the Cubs, perhaps more so than even the 2015 version that saw Theo Epstein land Jon Lester. Since their late-September collapse, the Cubs have overhauled their front office and coaching infrastructure — a new hitting director, pitching director, scouting director, manager, and a reshuffling of top-tier executives — in order to extract the most from their players and prospects.

The next few days will accelerate the next phase of roster transformation that has so far only seen bargain additions. That may still be the case when it comes to free agency, as the Cubs are reportedly telling people they’ve got to clear payroll just to make additions, but there could still be big moves on the trade front. And you never know, perhaps Theo Epstein has an ace up his sleeve. Or maybe at least a middle reliever.

Time to drink precisely one beer and use the following list as your definitive guide to what the Cubs will do over the next few days.

• Kris Bryant — The financially-restricted Cubs might be willing to listen to offers for their superstar. Multiple outlets have validated that the Cubs indeed could be entertaining Bryant trade offers.
• Willson Contreras — Several catchers have already moved to different teams this offseason. But since the market is very thin at the top, it’s possible that teams would be willing to give up value for Contreras, who is under team control through 2022 and has huge offensive upside.
• Nick Castellanos — According to Ken Rosenthal, the Cubs will need to move around money to sign Castellanos, who FanGraphs projects will receive $56 million over four years ($14M AAV). Perhaps the Cubs would entertain moving Kyle Schwarber to open up left field for Castellanos and to preserve Jason Heyward‘s position in right field.
• Kyle Schwarber — Believe it or not, Schwarber actually had a better second half than Castellanos last season. Schwarber made crucial adjustments to his approach and mechanics that ultimately led to MLB-best offensive production. Whether his hot second half gives the Cubs confidence to retain the left fielder is unknown.
• Ian Happ — Happ might have the biggest range of 2020 projections. He finished 2019 strong, posting a .264 batting average, 11 homers, and a .368 wOBA in 156 plate appearances. For his career, Happ owns a robust 112 wRC+ and .343 wOBA with 4.8 fWAR in 1031 plate appearances (2.8 fWAR per 600 plate appearances). Perhaps those improved numbers after several months at Triple-A will spur the Cubs move sell high on the utility slugger.
• Whit Merrifield — The Cubs have been connected to the Royals second baseman for quite a while, but the asking price for Merrifield seems outlandish. It might have to include Nico Hoerner, who has many of Merrifield’s same skills.
• Jason Heyward — While giving up on Heyward isn’t easy due to his defense and leadership, the Cubs likely will try to move his salary in order to clear room for other players. Trading that remaining $92 million over four years seems almost impossible, but the Cubs could move Heyward by including additional value in the deal, such as Happ or Adbert Alzolay.
• Tyler Chatwood — Though he is due relatively big money in 2020 (~$13M), Chatwood’s contract is over after 2020 and could be a fit for a team looking for a stopgap.
• Javy Báez — I’m not talking about Javy’s name in trade discussions, but the Cubs could finalize an extension with their shortstop if they clear up other roster decisions.
• Didi Gregorius — The former Yankee has not been connected to the Cubs yet this offseason, but he has the defensive and offensive chops that could fit well with the Cubs’ current roster. His ability to play across the diamond also would give new Cubs manager David Ross the ability to play Bryant in the outfield and selectively slot Hoerner in the lineup against favorable matchups.
• José Quintana — While the Cubs picked up Quintana’s $11.5 million option, they still might deal the lefty in order to free up payroll. Quintana has been roughly league average since the Cubs traded for him, but moving him is risky because few pitchers are as healthy and reliable. His contract is still a bargain for a solid starter, which is why the Cubs could get back a favorable return.
• Albert Almora Jr. — Almora was tendered a contract by the Cubs and is projected to make $1.8M in 2020, but it doesn’t guarantee a roster spot. If the Cubs decide to part ways with the outfielder, they can do so for around $300,000 early in Spring Training. Or they could use Almora in a trade, though not as a main cog.
• José Ureña — The 28-year-old righty touches upper 90’s and has showcased moderate command (career 3.06 BB/9) in Miami. Ureña is projected to make around $5 million in 2020, a price that Miami might not be willing to pay for a pitcher who just finished with a 5.21 ERA. He’s perhaps best known for giving up a home run to Happ on the first pitch of the 2018 season, so maybe the Cubs can bring him in for the mojo.
• Kevin Gausman — I want the Cubs to sign Gausman. There, I said it. He has one of MLB’s best splitters according to whiff rate and has maintained velocity in the 94 mph range. The Braves used Gausman as a starter last year, but traded him to Cincinnati because of his disappointing 6.19 ERA. The Reds immediately moved the big righty to the bullpen, where he struck out 11.69 and walked 2.01 batters per nine innings with a 3.17 FIP and 4.03 ERA in 22 innings. Gausman would give the Cubs starting and bullpen depth with the possibility for much more value than for what he will ultimately sign.
• Madison Bumgarner — The veteran lefty is projected to make $64M over four years ($16M AAV). Sign me up for that because there are several reasons to like the former Giant: (1) His velocity was its highest since 2015; (2) he pitched 207 innings last season; (3) his 30 years of age isn’t that old; and (4) he had success in 2019 with a 3.9 ERA and FIP.
• Pedro Strop — One of the best bullpen arms in Cubs history is on the market. Strop finished 2019 with a disappointing 4.97 ERA, but he was injured throughout the year with several injuries, which coincided with a velocity dip of nearly 2 mph.
• Infield depth — Several infielders on the market could make sense for the Cubs, including Brock Holt, Jose Iglesias, Jordy Mercer, Eric Sogard, and Tim Beckham. Holt might be of particular interest given their mutual Red Sox background. The 31-year-old utility player finished 2019 with an impressive .297 batting average and decent 103 wRC+ with a 9.5% walk rate and 19.3% strikeout rate. Holt’s positional versatility would give Ross flexibility to utilize Holt like a Ben Zobrist.
• Outfield depth — If the season were to start today, the Cubs would rotate Happ, Almora, and Heyward in center field. It seems likely that at least one of those will be subtracted and another outside name added. Current free agents include Shogo Akiyama — who has been connected to the Cubs already — and veterans Billy Hamilton, Adam Jones, Jon Jay, Cameron Maybin, and Kevin Pillar.
• Bullpen depth — Emerging performances from Brad Wieck, Rowan Wick, and Kyle Ryan, along with a healthy Craig Kimbrel, paints a clearer picture in 2020. The Cubs also have new pitchers Jharel Cotton, C.D. Pelham, and Dan Winkler to consider in addition to internal options including James Norwood, Dillon Maples, Justin Steele, Duane Underwood Jr., Alzolay, Chatwood, and Alec Mills. Still, it’s plausible to expect the Cubs to sign one more arm to bolster their depth. Possible relievers include Dellin Betances, Brandon Kintzler, Collin McHugh, Hector Rondon, and Blake Treinen.