I’m not sure any of these are foolproof upgrades. Maybe DeJong/Montgomery is, but that’s only because Anderson was god awful last year. DeJong’s ceiling is legit a 0.5 win player. That isn’t moving the needle and I’m not convinced Colson will be ready until the 2H and will likely experience some growing pains.
Grandal was bad last year, but Stassi didn’t even play in 2023 and he was awful in 2022 (in particular, check out his defensive metrics on Statcast). Hopefully that was a one-year aberration and perhaps his ability to handle a pitching staff can offset some erosion in framing, blocking, & throwing but there is a reason he was basically free. And you must not have watched Lee last year if you have any faith that he represents an upgrade over anything.
Beyond that, Nicky Lopez is the only positional player we’ve added. Again, he can be a useful little player, but doesn’t move the needle. Meanwhile, we have a massive hole in RF and zero OF depth. It’s hard to imagine that Benintendi, Eloy, Moncada, & Vaughn can be worse than last year. Any real improvement right now on the positional side will need to come from those guys and they are huge wild cards at the moment.
However, the part you really ignored is the pitching. How can anyone with a straight face say the pitching is better. Giolito & Clevinger actually pitched well for us last year and both are gone max. Cease is almost certainly going to be traded. Fedde & Soroka are fun little additions, but to expect them to replace the production of aforementioned guys is wild to me. And behind an incredibly questionable rotation, is an equally questionable bullpen. If you put a gun to my head right now and said predict the worst pitching staff in the majors, it’s going to be the White Sox. And it’s probably not even close. Right now, the pitching staff is almost certainly a large downgrade vs. the 2023 version and will get worse once Dylan is traded.
Unless the underperforming positional guys really improve this year and stay healthy, 100+ losses seems highly likely.