Jacob challenges him to "hack [his] static blog". I don't know what 'hacking a website' means to him, but to you and me it probably means compromising the web server, which is not directly related to HTTPS (although I can think of a lot of ways that the use of HTTP could lead to a web server being compromised).
Troy responds by taking him up on this challenge, accuses Jacob of thinking that his site is immune from transport layer risks, and then performs a man in the middle attack on himself using Jacob's site (when in reality literally any HTTP site could have been used).
It's like these two are having completely separate conversations.