Interesting thread.
Winninger's tenure included some real gems--Wild Beyond the Witchlight, Book of Many Things, Keys from the Golden Vault, etc. These are quirky, inventive, delightful books.
But it struggled to deliver old school, meat-and-potatoes core D&D. Sometimes you want the classic experience. You don't need inspiration, just competent execution. As one example, Shattered Obelisk was an unforced error. It could have been to Lost Mine of Phandelver what Curse of Strahd was to Ravenloft. Wouldn't that have been like totally awesome?
The relaunched campaign settings were a big missed opportunity. Those should have been accompanied by a Guild Adept program to expand the product line, hyping up the original creators, etc. The only setting that's had success is Eberron, and that's thanks to Keith Baker, not WotC.
To me, the biggest problem was lack of alignment between the products. WotC releases a Baldur's Gate adventure...years before BG3 comes out. When BG3 does come out...no adventure. C'mon, man! Bigby's Glory of the Giants and Fizban's Treasury of Dragons are great products...which would have landed harder if they were tied into giant- and dragon-themed adventures coming out at the same time.
To me, these are signs of larger dysfunction within the team outside of just the designers.
FWIW I'm a fan of 2024 D&D but it clearly suffered from a positioning problem. "No, it's not a new edition, but yes you should buy it."