It’s early in the offseason, but the Cubs look to be in pretty good shape for next year. Our Depth Charts currently have the team set to produce 41 WAR next season, which translates to around 85-90 wins. Even better for the Cubs, they are about six wins ahead of last year’s division-winning Cardinals and seven wins ahead of the Wild Card-winning Brewers. On paper, the Cubs have the best team in the division. That’s a pretty good spot to be in; the problem comes in trying to improve and win with the greatest core of players the franchise has produced in decades.

Over at The Athletic, Shahadev Sharma has a comprehensive look at the Cubs’ plans for the winter. The title gives a little away: “Cubs seem ready to make big moves, but don’t count on them spending big money.” Todd Ricketts’ comments on local radio station 670, The Score provides further insight:

But ultimately, now I think we can stop talking about windows. We should be consistent, and we should be looking toward building a division-winning team every year.

Theo Epstein sort of agrees. From Sharma’s piece:

“Next year is a priority,” Epstein said, before quickly looking ahead. “We have to balance it with the future. That’s probably more important now than it was even a year ago, because we’re now just two years away from a lot of our best players reaching their end of their period of club control with the Cubs. I think the goal is to do everything we can to win the World Series next year, but we also have to pay attention to the long term. Maximize this window while also putting in a lot of good work to open a new one as well.”

The problem for the Cubs is the near-impossibility of pulling off what Epstein proposes. To get a sense of how the Cubs are positioned, let’s look at the 40.6 WAR for which the Cubs are projected, and how long the players making those contributions are set to remain with the team:

The Cubs are very well-positioned for the next two seasons. While losing two key pieces of the rotation at the end of the year isn’t ideal, if Lester has a good season, the team can exercise a $25 million club option, which is only $15 million more than his $10 million buyout. After next season, however, the Cubs’ future looks pretty grim. The WAR figure is actually even worse when you factor in that Jason Heyward and Kyle Hendricks will be 32 years old, while Yu Darvish will be 35 years old; they make up about half of the remaining WAR from 2020 and their performance is likely to decline. The Cubs have some decent younger players in Contreras, Nico Hoerner, Ian Happ, and maybe Albert Almora Jr., but those players don’t come close to making up for the potential losses. Add in a below-average farm system, and there isn’t a massive influx of major league talent on the horizon, at least not by 2022. The team will certainly have the payroll room to keep some players in 2022, but Rizzo will be on the decline and Bryant seems likely to take the best offer in free agency, and the Cubs aren’t likely to have internal replacements for those two players’ production by the time it’s needed.

They could trade one or more of those players, but they couldn’t do so without causing a pretty severe decrease in their playoff chances over the next two seasons. Bryant and Báez would fetch the biggest returns, but Bryant might be nearly impossible to trade with his service-time grievance pending, and given his status as the Cubs’ best player, any trade would make the team significantly worse in 2020 and 2021 and maybe only marginally better in 2022 even if they received a high-end prospect in return. Similarly, Báez would be very difficult to replace as a starting shortstop. Rizzo seems unlikely to be traded given his stature with the club and with very little of equal caliber on the first base free agent market, the Cubs would find it difficult to replace him.

Schwarber seems like the most likely player to go, but as an offense-first corner outfielder, he’s only put up a 118 wRC+ over the last two seasons. A great second half last season might make him slightly more interesting to a trade partner, but he still seems unlikely to net a huge return. Teams looking to win now aren’t going to give up a major league-ready starting pitcher or impact position player for Schwarber when Nicholas Castellanos, Marcell Ozuna, and Yasiel Puig can be had for reasonable prices on the free agent market. And teams that aren’t looking to win now likely aren’t seeking a hitter who will be a free agent in two seasons.

If the Cubs are looking to extend their window, trading away stars, moving current contributors for small returns, or trading away more prospects accomplishes little. Dealing Schwarber for a slightly cheaper pitcher and then bringing back Castellanos would be more expensive for the Cubs and only make them slightly better. The same is true with Bryant and Báez, except the team will probably end up worse. Attempting to remain a postseason contender beyond 2022 is a reasonable goal for the Cubs, but if that means decreasing the team’s playoff odds over the next two seasons while their championship core is in its prime and under contract, then that goal becomes unreasonable. If the Cubs want to keep their window of contention open now and beyond 2021, the simple answer is just to keep the roster intact and look to the free agent market to address the glaring need in their rotation.

With Lester and Quintana likely gone at the end of this season, that need will only grow, and signing one of the better starters in this free agent class provides an easy way to get better this year and next year without sacrificing prospects, and buys the team more time to develop younger talent. The Cubs doesn’t need to get Gerrit Cole or Stephen Strasburg to cement their status as favorites in the Central. In looking at our Top 50 Free Agents, Madison Bumgarner, Zack Wheeler, Dallas Keuchel, Hyun-Jin Ryu, Kyle Gibson, Jake Odorizzi, Michael Pineda, or even bringing back Cole Hamels would all do a better job keeping the Cubs’ window open than trying to maneuver around artificial payroll restrictions.

The Cubs spent 2011-2015 with a mid-market payroll, averaging 12th in baseball over that time. They bumped payroll up above $200 million in 2016; few cared when it dropped by $20 million the following year due to the championship that preceded it. The team took a small jump in 2018 before taking a sizable leap last season as their young, cheap stars got a bit more expensive. As they begin their own cable network to broadcast all of their local games without sharing the profits with the Blackhawks, Bulls, and White Sox, the Cubs revenues are set to soar beyond those that have already made them the most profitable team in baseball over the past three years, per Forbes. The Cubs can talk about future windows, but they’ve got a big one open right now, and even a mid-range addition could prove hugely beneficial as they try to make it back to the postseason.