#3. Jonathan Coachman (with WWE from 1999-2008, and 2016 - 2018)
There's a pretty good possibility that Jonathan Coachman will be inducted into the WWE Hall of Fame someday. Not for his commentary - don't get me wrong, it was good, but not Hall of Fame good. He wasn't much of an in-ring performer, but he played a great toady authority figure during his run. Instead, he deserves to be put in the Hall alone for how the Rock treated him while he was there:
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Seriously, did any other interviewer take as much abuse from The Rock as The Coach did?
Coach would go from a commentator and backstage interviewer to an actual character, becoming the assistant to then-Raw GM Eric Bischoff. This also led to him actually particiating in matches - and usually (if not always) losing. John Cena even showed a video of him singing "I'm Too Sexy" in front of a restroom mirror, but I can't find it anywhere.
Coach left WWE for greener pastures... for a while.
In 2008, Coachman decided to leave WWE after his contract expired. Shortly thereafter, much like Todd Grisham, he found himself behind the desk on SportsCenter on ESPN. In 2015, the network formed a partnership of sorts with WWE, and Coachman was picked to interview WWE talent and introduce WWE-related stories.
It was clearly not having to do WWE content that caused Coachman to leave ESPN, because after a handful of months of leaving ESPN in 2017, he signed a new deal with WWE. He was placed in the Raw commentary booth along with Michael Cole and Corey Graves, although that only lasted for a little while. Near the end of that year, Coach was off commentary (replaced by our next contestant) and handling pre-show duties for pay-per-views - which I feel like I'm making sound like a horrible job when the fact of the matter is I'd do that job in a heartbeat if I was asked. Anyway, moving on.
With WWE not having much for him to do, he was able to use the company's arrangement with NBC Universal and, has since, covered the PGA for them.