James: Immediate future, not really. You don't trade an annual MVP threat in their prime and expect to immediately get better. Maybe if there was a big name prospect kicking down the door, but that's not the present situation for the Cubs. The only way it makes sense is if the Cubs treat 2020 like the Yankees did 2016: as a retooling year. If they aren't sure the team can take a step forward in 2020, then it might make sense to retool. If you can somehow get 3 safe, solid prospects who can make their big league debut in the next season or two, then I'd listen to offers.
Staci: There is only one way it makes sense, and that is if Thed get absolutely blown away by an offer and they're absolutely positive they can't re-sign him. Reasons NOT to trade Kris: he is "unklutch," he is "soft", he isn't good, he doesn't have TWTW. These are all meatball reasons that don't actually exist, and shouldn't even be spoken of. Sparkles is still the best player on the Cubs, and barring any sort of deal that would net them a gazillion prospects, allow them to trade Jason Heyward and sign Anthony Rendon, all the answers should be "NO."
Brooke: No. KB is the kind of talent you pay too much for in free agency, why would you trade him away now? These are his best years. Plus, they don't exactly have any 3B prospects ready for the show.
Matt: Not only no, but HELL NO. As the saying goes, those who do not study history are doomed to repeat it. Trading away superstars rarely works out. The Marlins traded Stanton and got Castro (2019 yikes dot com), and two minor league guys doing ok. The Bluejays traded Halladay and got no one of significance. The Mariners traded Griffey Jr. and got 2 years of Mike Cameron. The Rangers traded A-Rod to the Yankees and got back Soriano. So, the only way it remotely makes sense is if they trade him for Mookie Betts, and even then you're just spinning your wheels. If you do a 1-1 trade, you're basically getting back the same player but with 1 less year of control. You want to add a guy like Betts to a lineup with KB. AND you have no one to replace him at 3B. No. NO. NOOOOOOOOOOO.