"It's easy", they say. "Bring Kyle Schwarber, Kris Bryant, Javier Baez, and Anthony Rizzo back in 2021, and trade them.at the deadline when they have better value." It's bullet-proof logic, except for the large elephant in the room. Nobody else in the National League Central figures to be aggressively adding in free agency, either. The Cubs could very well look like an 88-win team that's a 37.8 percent favorite to win the division. Which could bring about a problem.
How much is a very possible "division title with a distinctively brisk exit" worth? The Cubs don't figure to bring back all of their core. Depending on the contract extensions they would demand (five or six years at rather peak values, in most cases), I can make a case against most. Depending on when any labor peace ceases, the Cubs could completely lose any compensation for any departing players. (Getting no return for losing Baez or Bryant would be particularly galling.)
Most sports fans lean emotional, and acknowledge logic. I'm on the other end of the spectrum. When the Cubs get to July with a potential division lead, I can hear it now. "They can't trade the players. Not while they're in contention for a playoff spot." I opposed the Nick Castellanos trade in 2019, when I saw who went the other way. While Castellanos upgraded the team, he didn't improve them enough to make them NLCS good. Or even close to it. If emotions drive the car, the car goes into warp drive when emotions rise. Which they will, until the obvious, "We weren't that good anyway" returns after elimination. However, the potentially added pieces are surrendered over irrational exuberance.
Does "2023 and beyond" matter?
If yes, attempts should be being made to acquire 2023 and beyond talent, pronto. Whether fans want quality youth added or not is unimportant. The youth movement in 2012 and 2013 was as popular as the bubonic plague in many circles. Until 2014, when Jorge Soler and Baez began to put faces on the rebuild.
The Cubs are a non-elite team at prsent, with plenty of likely free agents in their walk year. At some point, as with, say, the Rizzo for Andrew Cashner trade, the fan ought to pick a side. I can tell you what will likely happen if the same team, largely, represents the Cubs in 2021. They'll fall far short, because they aren't as good as the elite teams. A fan that picks a side in advance gets to assess their assessment value, afterward, and potentially learn from it.
Rebuilds will be harder the next time around, as teams are less likely to cheerfully give up quality future talent for rentals (for instance, the Matt Garza and Jeff Samardzija trades, and that Kyle Hendricks was fantastic). Keeping the same crew keeps a team that scored one run in two losses to the Marlins. Few logical Cubs fans see this squad as better than the Braves, Padres or Dodgers.
A white flag trade or three might be the best way to build for the future. Prioritizing emotion over logic, and eschewing future-minded trades, is a good way to lose unceremoniously in October. And potentially get no return for departing free agents. If you opposed the 2012 and 2013 trades, assess the reasons why, as you assess the possible trades that might come over the next month or two.