The Transom

Don King’s Axioms

While boxing promoter Don King may have filed a $2.5 billion suit against ESPN back in January for calling him a “snake-oil salesman” and alleging that he “killed not once, but twice,” he didn’t seem to mind when those same sentiments were expressed by Donald Trump and members of the Friars Club in a ballroom at the Hilton on Friday.

In fact, Mr. Trump, who looked unusually handsome onstage at the center of an endless banquet table of battered boxers and old comedians, led the luncheon off with “You know, he killed people,” and went straight to “Don King is a big fat fucking thief. He fucks everyone he touches.”

But a while after the soothing roast schtick of Mr. Trump and of Lisa Lampanelli—“I’ve had more black dick in me than the urinal at the Apollo”—came Paul Moody. Mr. Moody had a harsh rant about the evils of Gulf War II, and yet harsher words for Mr. Trump himself, who once placed newspaper ads that encouraged the death penalty for the perpetrators of the Central Park jogger case. (They were, of course, later found innocent.)

Mr. Moody told a dark joke in which the punning punch line was uttered by one genie to another: “Why would he want to be hung like a nigger?”

He then took Mr. King to task for his enthusiastic support of George W. Bush. This criticism, the only criticism of the afternoon, was the one that Mr. King, when it came time for closing remarks, chose to rebut with a mad flow of words.

“I’ve been the recipient of all this pain,” said Mr. King. He then told a meandering joke about a black man sleeping in a funeral home who was nearly embalmed in the morning by a staffer who said, “The nigger kept saying, ‘I’m alive!’, but you know how those niggers keep lying.”

“He’s rich!” Mr. King said, by way of explaining Mr. Trump.

“George Walker Bush is a revolutionary,” said Mr. King, in a dissertation on the perceptions of black people as lazy. “He did more for black peoples’ image than any other President in the history of the U.S. He took two shiftless, worthless, no-account blacks and made them Secretary of State and National Security Advisor.”

Mr. King continued: “He raised the bar of dignity, pride and hope, and inspiration. He did more against the Klan than anyone. Now they don’t have to slide-grind-slide like Michael Jackson.”

“Symbols,” said Mr. King without apparent humor, “are the strongest thing you could ever have.”

“They don’t have to be what they say they are,” he said.

“So some people got their benefits cut,” he said.

Back he went on track. “I just want blacks to take a stand and look at George Bush,” he said. “He’s a warrior! He says what he means and means what he says. So maybe he can’t be too intelligent. Warriors aren’t always intelligent.”

“Patriotism is the greatest thing in the world,” said Mr. King. “Any intelligent person will say, patriotism, if you analyze it, is insanity.”

One sometimes couldn’t decide whether Mr. King is a genius or an idiot.

“See this button here?,” Mr. King asked the crowd. “I’m a Screaming Eagle! The 101st Airborne! They’re out there defending the freedom we have today!” he exhorted.

“Treat your woman as your equal, not your superior,” reminded Mr. King.

“I love this country! God bless America,” he said in a sudden and triumphant close. “And God bless you, George Walker Bush!”

—Choire Sicha

The Lad Collects

Greg Gutfeld came back to New York to claim his rightful $2,000.

When he moved to London in June 2004, to edit the U.K. edition of Maxim, Mr. Gutfeld sublet his midtown Manhattan apartment to a then-friend. The then-friend forgot, Mr. Gutfeld claimed, to pay $27,000 in rent. After eviction notices and court appearances, the two have mostly settled up, but there’s still $2,000 that Mr. Gutfeld has yet to receive.

Of course, the small matter of this remaining debt (certainly small, no doubt, to the editors in chief of this world) was not the primary reason for Mr. Gutfeld’s visit. But it became clear on Sunday, after a few drinks in the faux-glam lobby of the Roosevelt Hotel where Mr. Gutfeld was staying and where, later that night and cash in hand, [ex-friend’s name REDACTED] was scheduled to appear, the money was certainly foremost in Mr. Gutfeld’s mind.

“He better have it,” Mr. Gutfeld said, nearly muttering to himself.

“What if he doesn’t? Am I going to have to kick his ass?” he asked his companion, U.K. Maxim features editor Dave Whitehouse, who had flown over with Mr. Gutfeld. “Nah,” said the young Mr. Whitehouse, who is barely intelligible underneath his heavy Midlands accent, “I’ll just take off my trousers and have my dick hang out.”

Mr. Gutfeld seemed pleased with this Plan B solution. [REDACTED] had, he said, a brain cyst, and that medical condition caused Mr. Gutfeld to worry about “kicking his ass” in a manner that might cause irreparable damage.

Seasoned fans of the New York media sport might find it interesting that Mr. Gutfeld would have any second thoughts about havoc. The man was ostensibly fired from Men’s Health because he made fun of cats, although he believes the unofficial reason was as simple as Dave Zinczenko wanting the job. He was fired, essentially, from Stuff for sending midgets to a Magazine Publishers of America panel. Most recently, his revival plan for Maxim involved large-scale features on feces and pubic lice; he only pauses in those labors (and only after a few pints) to pepper Arianna Huffington’s liberal brainy blog with talk of biodegradable anal beads. So one might expect Mr. Gutfeld to be a brutish meathead with little or no concern for much beyond securing a woman in his bed and a plateful of meat on his table (or, of course, the other way around).

But upon meeting Mr. Gutfeld, one is thrown off for several reasons. Mr. Gutfeld is short—very short, strikingly so. His diminutive stature is sharply contrasted by his shoulders and pectoral muscles, which are nothing short of hulking; they speak volumes to those long hours of “research” spent as the editor of Men’s Health. He talks incessantly and adoringly of his 24-year-old Russian bride, Elena, and carries with him an envelope chock-full of photos. And, most surprising: a bartender greeted his request for a glass of rosé with a blank stare, and so our hero settled for basic red wine. Rosé? Do you mean to say that the infamous Greg Gutfeld prefers White Zinfandel above all else?

“It’s because of the way they drink in London,” he said, eager to defend his masculinity. “They drink so much and so quickly.” He also noted that were he to drink beer at the typical English rate, his waistline would be considerably greater—“And if I drank liquor at that pace, I’d be through.” His adopted drinking rate is one every 20 minutes, interrupted only by smoke breaks.

Ah, London style. “You don’t have to kiss ass over there,” said Mr. Gutfeld. “The magazine culture there is much faster, they have these tabloids—five or six tabloids every morning. The stories have evil puns, half-naked women, stories of babies eating dogs. And they don’t frown upon people who are interested in going for those stories, and I like that!”

Mr. Gutfeld pulled out a copy of Pick Me Up, which resembled a vintage Tiger Beat that had been assaulted by a thin issue of People. It boasted headlines such as Helpless as my STALKER tried to BURN MY SON ALIVE and Love thy Neighbour: The girl next door sliced my Mel’s head off for £30!

“I love this stuff!” he said breathlessly. He leaned over while The Transom tried to absorb the adorably garish piece of gloss in its lap. It’s just so … different, so light and far more entertaining than the flotsam and jetsam spewed out of our local media machines. What, in God’s name, is New York’s problem?

“I think editors are generally really, really overpaid and coddled,” Mr. Gutfeld said. “They’re used to getting car services, perks. They spend most of their time talking to themselves. If you work at Esquire, you’re trying to impress your friend at GQ. Editors [in New York] like to think they can hold their own with higher media. I’m sure if I meet Jon Stewart, he’ll love me. As if they’re more interesting than the magazine they’re doing—and all these magazines are really boring!”

It was now four drinks into a lovely Sunday afternoon. One could have tried to not keep up with Mr. Gutfeld and Mr. Whitehouse. But: Yes! Boring! Another glass of Pinot Grigio, please! Let’s move to London!

“It’s not a new idea,” Mr. Gutfeld said, “but if you took any of these people outside the bubble of Manhattan, no one would give a fuck about who they are. People care more about their mechanic and the guy who sells them their washing machine than they do about who’s editing The New Yorker. New York incubates that kind of mentality. And you don’t have that in London.” Hello, Tatler? We’ll be at Heathrow in six hours!

But ah, that pesky $2,000. [REDACTED]’s hot date with the slightly intoxicated international collection posse was for the Roosevelt at 6 p.m. The Transom felt as if that confrontation might be most daintily handled without a reporter present.

But the next morning, Mr. Gutfeld called. “He never showed!” he shouted. “He even called multiple times to say he was on his way, so I think he’s a total con man. We waited for him all night. Do you have his name? It’s [R-E-D-A-C-T-E-D].”

—Jessica Coen

Heidi Klum’s Hidden Candy

For most of the night, Heidi Klum’s Sixth Annual Halloween Bash resembled nothing more extraordinary than your sixth-grade Harvest Ball. Debutantes in elaborate feathered hats, a tuxedoed man on stilts and a giant yellow M&M dressed as Darth Vader (complete with light saber), among others, lined either side of the dance floor, sipping their drinks and staring at one another, dancing within their own little spheres of personal space. Everyone was waiting for the celebrities.

And wait they did. A smattering of celebs didn’t begin walking the abrupt red carpet (a span of five steps at most from the curb to the door, nearly resulting in a photog bloodbath) until 10:30 p.m.

Ice T breezed past the crowd in a black leather coat.

“What are you dressed as?” he was asked.

“’Sup,” he said.

Jason Biggs crossed the threshold dressed as Dorothy Gale, with his girlfriend a cute metallic tin woodsman on his arm.

“We decided on Dorothy and Tin Man!” he said, nodding his braided brown wig and brandishing his checkered jumper. “My girlfriend was the Tin Man, so I was stuck wearing the skirt!”

But the real showstopper was Ms. Klum herself, sans baby. She arrived at a quarter to 10 (the Black Eyed Peas’ “My Humps” blaring overhead) in an outrageous black wig that towered three feet above her head, a tight black dress with a blinking red heart over her left breast and thigh-high leather boots. What was at first taken to be a black gossamer cape revealed itself as wings when she bum-rushed the row of cameras, baring her garish faux fangs. Only Ms. Klum somehow managed to make it sexy, not creepy.

“I’m Draculette!” she said. Obviously.

“Seal is in L.A.,” she pouted. “That’s why my heart is bleeding.” Indeed, the glowing red heart on her chest leaked plastic streams of blood across her bodice.

Benji Madden from Good Charlotte cruised in, wearing his usual uniform of black. Black sweatshirt, black hat, black eye makeup.

“I’m not dressed up as anything—no wait,” he said. “I’m dressed up as Benji from Good Charlotte.”

A flurry of activity broke by the door with the whispered rumor that Seal was coming to surprise Ms. Klum. Somehow the news leaked to her—or it was all a clever P.R. stunt—because as Mr. “Kiss from a Rose” himself arrived dressed as a traffic cop, Draculette rushed out the door and embraced him before the cameras outside. His grand entrance was interrupted, however, by a drunk guest passing out inside. She was lifted by a handful of suited security guards and carried outside. No one could see what she was wearing.

Ms. Klum gave Seal’s ass a nice rubdown. They moved their public displays upstairs and started dancing.

A Nancy Drew told The Transom that while Seal was outside, the bodyguards were telling people to clear out of the way—and for a moment, even Valentino was brushed aside. Until he spoke up.

“He was really cool about it,” she said.

—Nicole Pesce and Erin Coe