What a strange title.
The author was suggesting “when pigs fly”. He is taking the Daleys at face value. Bill is trying to get the votes of those who are nostalgic for the Ruchie Daley days and also present himself as a reformer. Once in, he can say that the needs of 2027 are different than the needs of 2019. Or he can flee a burning ship like Richie Jr did. Win Win.