That's because much of the tech press prefers sensationalism to get clicks over accurate reporting to inform readers. Here's a comment I made last week on another forum that covers what the tech press should have told us about Wheeler a long time ago, but didn't.
It's important to note when he worked for cable. Much of the reporting in the tech press gives the impression he came straight from some high paid lobbying job with Comcast to the FCC.
In reality, he didn't work for any one cable company, but rather was the president of their main trade association, and that was from 1976 to 1984. That was a time when the internet was still just for military, defense contractors, and major computer science and engineering universities. There were around 1000 computers on the internet then. The opening up of the internet for civilians, starting with the creation of NSFNet by the National Science Foundation, wasn't to start until 1985, and it wasn't until 1992 that the web was released.
So when he was a cable guy, it was all about television. Cable as an industry was also much smaller than it is now, and it was divided among many more companies. They were the upstarts, challenging the big broadcasters. Being pro-cable was arguably being pro-consumer.
From 1992 to 2004, he was president of CTIA, the main cellular trade group. By then, the public internet was well under way, but it was mostly wired. Internet on phones was available, but it was more of a novelty or an expensive luxury, with voice and text being the main interest most people had in cellular. CTIA lobbied, of course, but they also had a major role in setting technology standards. Wheeler represented the industry in discussions with the FCC to draft the rules that we now have for cellular voice, which in retrospect worked out well (and are the basis for the Title II proposal he's expected to reveal).
It's also important to note that cell phones in 1992, when he joined CTIA, were not nearly as common as they are today. There was much less infrastructure in place, and you paid by the minute. They were past the point where you'd stare openly in wonder if you saw someone with one, but still were something you had to work to find a good reason to justify their purchase.
The key thing to note here is that when he has worked as a sort-of lobbyist (I say "sort-of" because both times he was president of a trade association that had lobbying as just one function), it was for industries that were young and had a lot of promise to bring great things to consumers, and his work for those industries as far as I've been able to tell helped consumers, and the customers of those industries were better off when he left than when he started.
He seems to basically be a telecom policy nerd. Heck, he even does telecom stuff in his non-professional capacity. Only a telecom nerd would write a 250 page book called "Mr. Lincoln's T-Mails: The Untold Story of How Abraham Lincoln Used the Telegraph to Win the Civil War" .
Wheeler has been one of the three members of the FCC favoring pro-neutrality regulation for quite some time. Its true that he recently came around to the view that Title II was an appropriate vehicle for that regulation, but he's been a supporter of FCC action to enforce neutrality principles for quite some time, as demonstrated by the previous Open Internet Report and Order, the last NPRM in which he took one of the two paths toward enforcing those principles laid out in the court decision striking down the old Open Internet Report and Order, and his new move to use Title II, the other path laid out in that court decision.