If I recall, tom7 was at odds with chrome throwing up a warning at users trying to visit his website because he didn't support TLS on it. He wasn't against TLS. Calling them a TLS antivaxxer is not accurate.
ISP injecting ads is like annoying but if someone knows as much as Tom about TLS and totally skips rouge "airport wi-fi" can use his website to own someones else device that is the argument I should use for calling him or anyone else names on the internet.
I guess Kazakhstan example kind of covers it, because I do believe they would definetly deliver malicious payloads to dissidents.
While he does indeed have extensive knowledge of TLS/SSL. He still completely side steps points I wrote about and exaggerated many minor inconveniences. While PDF seems quite up to date it also picks on stuff that is not there anymore like green padlocks.