Part of the schtick was that the Cubs were going to have such a great winning environment, and that Theo and management were going to treat players so well, and that there was going to be such a great culture, that players were going to WANT to stay, and that other teams would need to super-outbid to get guys to want to leave. The Cardinals would acquire players, and have it be such a great place that guys would routinely sign extensions. Doesn't appear that the Cubs have actually ended up creating that.
Perhaps that will improve? Back in 15 and 16, the Cubs felt like they were on the rise, the young happening thing with the great future, kind of unexpected, everything clicking. Theo and Hoyer seemed to have a magic touch, clicking on deals like Arrieta and Fowler and Rondon, Schwarber being a quick hit, etc..
Since then, it seems like the burden of expectation has been heavy, and that nothing Theo/HOyer have done since has clicked, and that despite the many wins, 17 and 18 felt kinda disappointing.
But now there will be zero burden-of-expectation. Maybe this will be a year which is unexpectedly and refreshingly fun and exciting? Unexpected cats like Wick and Wieck and Hultzen and Wickler emerging; Bryant getting back into MVP discussion; Schwarber and Happ emerging as good hitters; Hoerner not only sustaining but improving and looking like the real thing; some unexpected rotation pitchers emerging as really useful (Chatwood, Alzolay, Abbott....) Being the thrilling underdog overachiever will be super fun, and with Lester and Q coming off payroll perhaps the payroll won't look nearly so burdensome next winter? Plus Davis and Marquez will have super years, and suddenly the farm will look like we've got some winners on the way... David Ross will have the team working hard and camaraderie being terrific. All of the new analytics guys will be improving players and having players feel like this is the place to optimize their game.
So perhaps next winter this will very much feel like a place where a Bryant very much does NOT want to leave, where it's NOT a collapsing sunset team but has a bright future, and where a fair-market extension will be both very appealing to him, and very accessible to the Cubs? Why not?
In terms of contracts, Bryant has two more years. Lester, Q, Chatwood, Morrow, Kimbrel, all of those contracts will be gone. Even the Heyward obligation will have only two more years left, the end in sight. It's not like we've got so many stars that we won't be able to afford to pay market-price for the couple of them worth keeping. Not sure why you couldn't fit all four of Bryant, Baez, Schwarber, and Contreras under the lux level, if you had some effective thrift-priced pitchers. So the premise that the big-market Cubs can't possibly compete on the market if they let Bryant reach the market seems unnecessary.