Many times during the trial, lawyers for Gawker, the gossip website Hogan sued for posting an excerpt of his sex tape online, played clip after clip of Stern asking probing questions about Hulk Hogan's (real name Terry Bollea) sexual exploits.
It almost felt like Stern was on trial too.
So it was no surprise that throughout the trial, Stern shared his thoughts on air. This week, he talked about the outcome.
"I want to say, I am so happy that Hulk Hogan won the case against Gawker, and I'll tell you why," he said.
As an advocate for free speech — well, mostly just his free speech, he admitted — Stern said he thinks Gawker's attempt to make the case about free speech is "a total load of" words unfit to print.
"I truly believe that you can't just say this is a free speech issue," he said. "This is the same as Erin Andrews being in a hotel room and some guy drilling a hole in the wall. You can't take a tape of somebody that is illegally made and just post it on your website and say this is news and free speech.
"It isn't. It's an invasion of privacy."
Stern has a personal relationship with the sex tape controversy's primary players.
He had Hulk Hogan on his radio show several times over the years.
He once employed the tape's alleged maker, Tampa radio shock jock Bubba the Love Sponge Clem, and attended Clem's marriage to Heather Cole, the woman copulating with Hulk in the sex tape.
Most disturbing to Stern, he conceded on air, was that it could have been him on that tape. More than once, Clem had propositioned Stern to have sex with his now ex-wife, just like he'd done to Hulk Hogan.
But Stern just thought he was kidding.
"Oh, I would die if there was a sex tape of me," Stern said. "I would be humiliated."
Mid-show on Monday, Stern called on his producer to try and get Bubba, who was also live at the time on his own show, to call in for a conversation about the trial.
Stern and his longtime co-host Robin Quivers compiled a list of questions for Bubba while they waited.
1. Do you still love Hulk Hogan?
2. Why exactly did you make that sex tape of Hulk and your ex-wife in the first place?
3. Who else did you solicit to sleep with her?
These were all questions that lawyers on both sides during the trial never got the chance to ask. When Bubba was called to testify, he pleaded the fifth and never showed up in court.
To the first, Bubba responded: "I still would like to be his friend.
"I did something that I'll pay for for the rest of my life… I don't necessarily know that I would expect him to ever forgive me and what I did, but I own it, I did it... It's tough to know that I made that decision in life, for whatever reason and there's a lot more than I can't talk about."
That foreboding response intrigued the hosts, who pumped Bubba for more information, which led to question No. 2: why?
"I can't answer that," Bubba said. "Two wrongs don't make a right, Howard."
Then he launched into a long tale that verged on conspiracy theory about how the DVD eventually made it into the hands of Gawker.
It involved a disgruntled former employee who sold it to one guy who gave it to another who sent it to Gawker.
What was most interesting was when the hosts prodded further about the existence of other tapes and Bubba's repeated ambiguity about the creation of the Hogan one.
"Was there a list of people that were acceptable for this kind of transaction?" Quivers asked.
Stern added: "There was me and Hulk Hogan."
Then Bubba got weird.
"I'm going to leave it with this, just be careful guys, where we're going here," he said. "I'm like a moray eel right now, my mouth is wide open and you guys are tempting me with your hand. And if I give you the data and I clamp down on it, it's going to ruin lives. Howard's dancing with me, you know what I'm talking about."
Stern didn't, and he said so.
Contact Katie Mettler at email@example.com or (813) 226-3446. Follow @kemettler.