Good morning and welcome back to the Tip Sheet, a weekly newsletter from Tom Dudchik’s Capitol Report written by Mike Cerulli.

This week, we’re breaking down the conviction of Kosta Diamantis and Chris Murphy’s latest interview with one of the most interesting figures in American media. Plus, there’s a new investigation into absentee ballots in Bridgeport. Yes, another one.

Let’s dive in…

Diamantis convicted on all 21 counts

It took a little more than one full day of deliberations for the jury in the Kosta Diamantis trial to return guilty verdicts on all 21 counts of bribery, extortion, and lying to federal investigators.

The Lamont administration’s former deputy budget director and school construction boss is set to be sentenced in January and then go on trial again in a separate federal bribery case.

You can read Andy Brown and Dave Altimari’s recap of the trial here.

Murphy talks loneliness, Trump, and Cum Town with Adam Friedland

Mark it down in the history books, folks. Chris Murphy is officially the first United States Senator to say the words “Cum Town” on the record.

For the uninitiated, Cum Town was a comedy podcast hosted by Adam Friedland, Stavros Halkias, and Nick Mullen. The show had a six year run from 2016 to 2022 – gathering a cult following and advancing a movement that is reshaping American politics.

Throughout the show’s run, its hosts were often lumped in with the so-called “dirtbag left” movement that includes other podcasts like Chapo Trap House. In the broadest sense, the term “dirtbag left” typically refers to a group of media figures who embrace a politics that is more anti-capitalist, more vulgar, and more populist than mainstream liberalism.

Many of the figures associated with the dirtbag left were supporters of Bernie Sanders during his two presidential runs. Cum Town alums Mullen and Halkias have both publicly boosted Zohran Mamdani’s upstart campaign for mayor of New York City.

Friedland, the other former Cum Town cohost, has gone on to build a highly influential solo show published on YouTube and podcast platforms. In recent months, his guests have included the Silicon Valley congressman Ro Khanna, former adult actress Mia Khalifa, conservative commentator Michael Knowles, and six-time NBA all-star Blake Griffin. 

The media-driven narrative that the left must find an equivalent figure to Joe Rogan helped push Friedland’s post-Cum Town enterprise further into the mainstream.

“The futile pursuit to find the Joe Rogan of the left has put a spotlight on Friedland and the buzzy weekly YouTube talk show bearing his name that courts a young male crowd,” the New York Times wrote last month.

A May headline in GQ Magazine mused that Friedland could be the millennial generation’s Jon Stewart.

For his part, Friedland has responded to his newfound attention with his signature brand of self-deprecating humor. He’s poked fun at the glossy write-ups heralding him as the newest political media star, while at the same time bringing on an increasingly influential line up of guests.

Ritchie Torres, the moderate New York Democrat, appeared on the show shortly after Khanna and faced a grilling on his support for Israel that quickly went viral. David Hogg, the Parkland school shooting survivor who was ousted from a position at the Democratic National Committee, had a conversation with Friedland about the future of the Democratic Party.

Murphy is arguably the most prominent political figure to appear on the latest iteration of Friedland’s solo project. His interview touched on a wide range of topics, from his roots in Connecticut to the end of his marriage.

Friedland’s unique and earnest interviewing style has a way of drawing out answers that you just don’t see in the mainstream press. Going on his show might be seen as a risk for conventional politicians who want to avoid an awkward moment or the unvarnished scrutiny of a comic who deploys irony with almost unmatched skill.

As Murphy said, going on shows like Friedland’s are “a new part of the job” for politicians.

“It used to be that, like, you could just do, like, two cable shows, maybe if you were a big deal you’d show up on late night TV,” Murphy said. “Now, you know, you used to do a show called Cum Town.”

“You used to be from the red onion capital of America,” Friedland countered. “So, we both have a checkered past.”

You can watch the full interview here.

Too many to count: another ballot investigation in Bridgeport

Here we go again.

The State Elections Enforcement Commission has referred yet another case of alleged absentee ballot misconduct involving a Bridgeport elected official to prosecutors.

Alfredo Castillo is no stranger to such allegations. He’s facing dozens of other charges related to the 2019 and 2023 elections.

Read Ethan Fry’s write up here.

Odds and ends

• UConn Law School’s alumni association will honor Matt Ritter with their Distinguished Graduate Award this week. Natalie Braswell, the governor’s chief legal counsel and former state comptroller, will receive the association's Public Service Award. Both graduated in 2007. Previous recipients of the Distinguished Graduate Award include Andrew McDonald, Thomas Meskill, and Tom Ritter.

• Feeling lucky? Connecticut hit $2 billion in sports wagers in the month of September.

• The “Sub Capital” steams on. In a meeting with the Australian prime minister, President Trump threw his strong support behind the continuation of the AUKUS submarine deal. PM Anthony Albanese deplaned back home wearing a Joy Division t-shirt, which the Aussie press said reflected a “rock star” status following a successful trip to the U.S.

That’s all for this week. We’ll be back next Monday with another edition of the Tip Sheet!