My guess based on what we have heard.
Plan A was to draft Kris Murray, use the MLE and/or BAE for a young wing and Sasha, use bird rights on Barnes and Lyles, and then mostly run it back, but with Kris, Sasha, and another cheaper wing (Brown, Bey, Keita, etc…).
Plan B is if Kris was off the board, then we pivot. I’m guessing we liked several draft wings equally well, but liked them slightly below Kris (and maybe Jaime Jacquez) given that those were win now prospects. We probably had guys like Jones and others ranked in the same tier, so there was hope we could trade out of 24, and still get someone we wanted at 38 (or if we were worried we could trade up from 38 for a more modest price). In this plan, instead of investing in HB/Kris/cheaper wing, we invest in one home run wing and a draft prospect. I doubt Kuz was the target. Feels like Middleton or Grant. Or the trade cap space for Beal, OG, Siakam options. Middleton said no and Grant is now a priority for Portland. Maybe Kuz was an option, but given the Houston rumor, I am guessing Kuz is going to be 4/100, and Monte said no.
Plan C. If Middleton, Grant, or a trade aren’t options, then don’t panic on a lower tier guy. Make up with Barnes, use cap space on a younger/cheaper wing (like in Plan A), extend Domas, bring Sasha in the room exception, and resign Lyles with bird rights.
To me, that is a smart, calculated, low risk swing. The potential difference from plan A and C is so small, that it was worth the risk to try plan B, even if you strike out. In both plan A and C you run it back with HB and Lyles, add Sasha, add a young/cheaper wing in free agency, and have a draft pick join our rotation. The cost of taking the free agency big swing is trading 24, but if you valued Jones at 24, then you really lost nothing. There wasn’t really rotation room for adding a guy at 24 AND 38 on an already winning team with Keegan, Sasha, and HB/free agent, so getting one guy you wanted with those picks and taking a swing in free agency seems calculated. Plus, by getting off Holmes and swinging (and missing) in free agency, you have the fall back benefit of locking up Domas for a good deal when there is no competition.
So maybe it didn’t work out the way Monte wanted, but he seems careful and doesn’t leave his flank exposed. It seems like maybe he took a swing, knowing that if he missed he could still get most of what he wanted with little exposure. The key (and it seems like he realized this) is not panicking if his big swing didn’t work out, and getting himself into a bidding war on someone like Kuzma with a loser team with lots of cap space like Houston.