I don’t really want to dive into politics too much, but no, this doesn’t require losing, but I do think he expected to lose. I think if trump won in 2020 he would have pushed for a new tax policy which preserved or even added cuts and “restarts” the cliff in the 2024 term. The “big beautiful bill” which recently passed also adds cliffs for additional stuff, and he’s claimed he wants to be elected in 2028.