It’s really going to be a challenging deadline. There is a cost to trading, just as there’s a cost to having those guys walk for nothing. If Stroman gets traded, he will likely be THE best starter on the market…but the Cubs don’t have to trade, so if they move him, it should be for multiple ML-ready or very near ML-ready players. If you don’t get that return, don’t trade him. Same for Bellinger. Gomes has a team option for 2024 ($6.5M against the CBT or a $1M buyout) - if you plan to compete in 2024, I think you bring him back as Amaya’s backup. We’ll see about Barnhart, but the emergence of Amaya might mean the Cubs eat his $3.25M for next year.
As for thinking you can win the division, I think there’s still a path there. I’m actually not convinced the Cubs are worse than the Brewers. I also don’t trust the Brewers to not sell at the deadline (they traded Hader last year while leading the division). Cubs certainly aren’t the favorite from here, but the schedule lightens up in the 2nd half (that might not be good for the Cubs as it seems they play better against better teams), so dealing the best hitter and the 2nd best starter likely takes any chance out of play.
This team still needs at least one major bat in the middle of the lineup, to not be an offensive black hole at 1B & 3B and improve the pen. The Cubs would need those upgrades right now for 2024. If you don’t extend Stroman, then you also need to add a top line starting pitcher. I think there’s a solid deal to be had with Stroman. I take him at face value that he doesn’t want to leave. He pitches very well at Wrigley and he’ll continue to have an excellent defense up the middle for the next several years. I think he’s actually going to age ok over 3-4 more years and as he hits the age curve and goes from being a #2 to a #4, hopefully the Cubs have other young starters moving up the rotation.
I have to think Jed’s seat starts getting hot soon, too. I know it’s popularly cynical to say that Ricketts doesn’t care about winning, but Ricketts does care about money. They’ve been missing revenue targets on Marquee from the beginning and are now launching Marquee direct to consumers. They also built the sports book and own a crap ton of property around Wrigley. The better the Cubs are, the more those other things hit targets. Also, even if Tom never spends beyond what they spent from 2016-2020, that’s enough to win if you spend it reasonably well. Tom may not want to be Steve Cohen, but there’s no chance he wants to put out a competitive payroll and lose.