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The Media Column: Bill Simmons' fawning interview with Jake Paul is the low point of his career

Bill Simmons welcomed ultra-famous YouTuber turned boxing star Jake Paul on his podcast and never mentioned the two sexual misconduct allegations levied against him in recent months. Instead, they commiserated about cancel culture.

While Simmons has never branded himself as a tough interviewer, that kind of acquiescence is downright malfeasance. The media mogul runs one of the most culturally progressive sports websites out there, yet consistently falls short of his outlet's own standards, and in this case, the standards of respectability.


For those who are blissfully ignorant, Paul is one of the more notorious "social media influencers," though he doesn't spend his time hawking products or posing in bubble baths. Paul and his brother built up their following through committing dubious stunts and pranks, such as when Logan visited a Japanese forest where people are known to commit suicide and filmed his encounter with a corpse.

The backlash threatened to end their YouTube careers.

With criticism mounting, Jake and Logan turned to boxing, where outrageously offensive behavior is encouraged. And as it turns out, they're pretty good. Jake Paul is 4-0, racking up a split-decision win against former UFC welterweight champion Tyron Woodley.

Meanwhile, Logan Paul took on Floyd Mayweather Jr. in an exhibition match last June, and it reportedly drew more than 1 million PPV buys.

Simmons asked about all of that, and portrayed the Paul brothers as victims of an unforgiving social media climate. "You're making mistakes in real time. The cancel culture stuff is really starting to kick in. In the 2017-18 range, people are just getting mad constantly," Simmons said sympathetically. "At some point, it either seems like it breaks you, or you kind of figure out, 'Where do I fit into this whole thing?' One of the things I thought was interesting about both you and your brother is, you've both had these moments, you've worked through them, and you've kind of figured out, 'Alright, I'm just going to kind of own this.'"

The "cancel culture stuff" that Simmons is referencing probably invokes the outrage Pauls' neighbors directed towards them in 2017, when they considered suing the brothers for making their neighborhood a "living hell." Or maybe he's bringing up the looting. Paul was charged last year with criminal trespass and unlawful assembly for his alleged connection to the looting of a mall during the George Floyd protests (the charges were eventually dropped).

There's also the aforementioned sexual misconduct. In April, the TikTok star Justin Paradise accused Paul of sexually assaulting her in 2017. A couple of weeks later, another woman told the New York Times that Paul had groped her in 2019.

Understandably, Simmons probably wouldn't have landed the interview if he broached the sexual misconduct allegations. But so what? Simmons is estimated to have a net worth of $100 million, and his podcast is the No. 3 most downloaded show on Apple Podcasts. He doesn't need Paul for fame or fortune. The benefit of interviewing Paul isn't worth the embarrassment of fawning over him.

That is, unless Simmons just wanted to do it. For whatever reason, it's apparent Simmons was focused on rehabilitating Paul's reputation. If you listened to the podcast and didn't know about Paul's past, you would walk away feeling sorry for this poor dreamer who flew too close to the sun.

"It was rough at first going through these 'cancel' moments and being hated on," Paul said. "I had no one to talk to about this, because it was the first time kids this young were exposed on the Internet for everything they've done … or not done."

Nice save, kid.

"Bill Simmons fawning over Jake Paul is bad enough. But commiserating over cancel culture with a guy accused of multiple sexual assaults is another level," tweeted Isaac Chotiner of the New Yorker.

Twenty years ago, Simmons rose to prominence for exposing staid sports media people in hilarious and sometimes humiliating ways. The Boston Sports Guy spoke to a generation of disenfranchised Gen Xers, and rode his brand all the way to a nine-figure fortune.

Of course, Simmons has now become everything he derided, but he's maintained his cultural cache through The Ringer and other critically acclaimed ventures, such as ESPN's "30 for 30" series. To Simmons' credit, "30 for 30" is consistently excellent. He sold The Ringer to Spotify for $200 million last year.

Despite that success, there seems to be a schism between Simmons and his staff. Last year, Simmons and Ryen Russillo apologized for their commentary about the Floyd protests on Simmons' podcast. Russillo chastised "looters" for "breaking into sneaker shops," while praising Simmons for his diverse hiring practices.

The Ringer Union noted in a Twitter post the site had no Black writers or editors covering the NFL or NBA, said that more than 85 percent of the speakers on Ringer podcasts the previous year were white.

Now, we can quibble about whether Simmons deserved to be publicly rebuked for that podcast, but there's no doubt here. It's a horrible look to interview Jake Paul and not bring up the allegations he's facing.

Talk about being out of touch.

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RemDawg the Institution: Jerry Remy was an excellent baseball analyst. He was able to intricately break down the art of hitting and had a penchant for being ahead of the action. But that's not why he was a cultural institution.

It was his sense of humor, and on top of that, his vulnerability.

Over the years, we learned about the trials of Remy's personal life. It was painful to see him battle cancer seven times, and the depression that came with it. Towards the end of his life, Remy opened up about his lifelong battle with crippling social anxiety. Last season, he brought it up when Zack Greinke, who's also battled social anxiety, faced off against the Red Sox at Fenway.

"I give Greinke an awful lot of credit," Remy said. "For a guy that's been through what he's been through — and I know, because I've battled both of those, anxiety and depression — no fun. To be pitching at a high level and the big league level for as long as he's pitched, he deserves a ton of credit."

Remy's openness about the topic further ingratiated him to millions of Red Sox fans, including a kid from Natick who's undergone similar struggles. Remy wasn't only the RemDawg. He was a real and vulnerable person. What a loss.

Why Aaron Rodgers' vaccination status is our business: Former Patriots tight end Benjamin Watson tweeted Wednesday that "COVID vaccination status never should've been public knowledge. Media shouldn't have been permitted to interrogate NFL players about themselves or teammates."

With all due respect, Watson is wrong. Rodgers' vaccination status matters, because it's now impacting his availability. He'll be out Sunday due to COVID protocols, and could return one day before the Packers' game against the Seahawks Nov. 14 — at the earliest. His absence may cost the Packers home field advantage.

For people who cover and follow the football team, that matters.

Rodgers' ruse: Rodgers lied about his vaccination status. While he told reporters he was "immunized," in the following breath, he talked about how he wouldn't judge teammates for being unvaccinated — indicating he's not one of them. The Packers' QB also behaved like a vaccinated player: he didn't wear masks on the sideline during preseason games, and hasn't worn one at press conferences — luxuries only afforded to vaccinated individuals.

I'll save you the moral handwringing about how Rodgers was putting others in danger, and leave you with this: at least Cole Beasley and others were honest. Rodgers' deception raises a bevy of character questions, none of which are good.