This is no shot at you personally, but I would despise this kind of a deadline. This is the thread the needle nonsense they've been flirting with for a bit. The Chicago Cubs are a top-5 market and realistically need to stop acting like a reclamation team. Especially if they're keeping Bellinger and Stroman. If you're keeping them you're shooting for the playoffs, and 2 months of reclamations isn't enough time to make a true determination. So we enter 2024 with more of these projects...some might work out, most will either marginally work out or will fail. I think a "hold+under performing MLB" deadline is probably the worst case outcome; it banks on this flawed Cubs roster making the playoffs and it doesn't give you enough time to properly evaluate the under performers for 2024. So you really can create a whole host of new questions instead of solving anything. These feel like trades you make in December, not really in July. So while I don't think they're a bad idea on their own, as a July-deadline trade they feel out of place.
Sometimes trades for non-elite-today prospects don't work out, but I'm also not advocating the Cubs buy half a HS prep lineup like they did in the case of Darvish. There's middle ground between 18 year Olds with zero professional PAs and players in high A with a few hundred PAs of data. In fact, the QO play is a lot closer to that (you'd be likely targeting prep hitters or arms with those picks and slot). The Cubs should be able to do considerably better selling on those two and 18 year Olds. I'm not entirely sure exactly what to expect for either, the deadline is a fickle lady and teams can get swept up, or decide to just stand pat, at a whim, so I'll avoid offering names (especially with the Cubs and how they choose MiLB talents off the radar). These can be prospects that are used to restock the system as the Cubs use their prospect depth in the offseason to grab some actual talent. Or players used to aid those trades. The Cubs do have a ton of talent in the MiLB, but it can't be a bad thing overall and can be used in many ways.
As stated I feel like the Cubs need to pick a lane for once. Thread the needle rarely works and I think we have enough information these last few seasons to show it might not be Hoyer's strong suit. I'm not sure he's aggressive enough for a lane in which we actually upgrade the team either, but I'm not sure it's to be seen he can't either. I'm very firmly I'm the camp that the Cubs either need to get max value today for the Bellingers/Stroman/Gomes types and then commit to Amaya, Mervis, and a few on the cusp younger players, or they need to add players who will actually support these players to make a true Playoff push. I can't see many outcomes where the middle ground pays off in any way for the Cubs except for, maybe, Tom Ricketts profit lines. It might be slightly more fun for us, but long term Cub success...I'm just not that does anything.