So my thoughts, just to get them on paper (or internet paper) on the deadline:
In a vacuum, I really have no issues with any trade the Cubs made. You can quibble on a prospect here or there, but the highest-ranked prospect traded profiles like a backup, and your best upside is a kid who isn't even-18, so he'll almost assuredly fizzle out. The Cubs got a perfect bench bat in Castro, an undervalued SP in Soroka, and two arms to help the bullpen. The Cubs are unquestionably better than when we last saw them.
But...I think this is a failure of a deadline from Jed Hoyer. His best asset as a leader is that he holds strong to his valuations of players. I love that about him. It's why I liked every trade above; the Cubs didn't get fleeced once - they really don't get fleeced. Maybe you don't love a trade but they never get fleeced. But it's that same pigheaded valuation that means you never get irrational for needs.
Jed Hoyer is a fine VP of Baseball Ops. He put together this roster, and the Cubs look like a team who can make the playoffs. They're better than yesterday. But sometimes you need to pay 15% more than you should just to have it and Jed's undying loyalty to the value means that while he won't get fleeced, he won't go big.
One of our other writers, put it best in our slack today. "Jed always picks up his pizza, he never orders delivery" and I think that's the best analogy I've ever heard for Hoyer. He will never pay the delivery fee, he'll never pay for a tip if he can just drive seven minutes down the road and get it from Dominoes. I don't think he needs to Door Dash McDonalds every night like AJ Preller probably would, but sometime, he needs to treat himself.