I wasn’t as quick as you. About four years ago for me. The clincher was when be became a never-Trumper. I turned him off in the Spring of 2016.
I tuned him in again for a few weeks after the election just to hear him have to eat crow.
I saw Hewitt’s establishment leanings when he was shilling for Romney, not just as the only alternative to Obama, but actually as a purported “good candidate.”
The thing about Hewitt is that he lied about his position during the 2016 election cycle. He was never Trump, but always claimed to be neutral. It was a bald faced lie, but he fed it to his audience daily.