Getting an interview with Trump was much tougher. After an embarrassing number of unctuous calls and emoji-and XOXO-laden emails to his longtime secretary Rhona, I was finally granted the opportunity to grovel at his 5th Avenue office and pitch him the idea myself.
Trump came out and greeted me warmly （this was before our fun encounter at the Polo Bar）。 “Great to see you!” he said. “Come on in.”
Radiant city views filled the windows. Trump’s desk was the size of a dining-room table, and it was covered in magazines, all bearing his mug （or a facsimile thereof）。 Stacks of magazines, six copies deep: Time, New York, Rolling Stone, the Economist, Esquire, People, GQ…
“Can you believe this?” he said, waving a hand. “Can you believe this?”
“No. I really can’t,” I said honestly. Then he told me how much “the evangelicals” liked him as I glanced at a framed, blown-up copy of him on the cover of Playboy. Knowing I didn’t have much time, I quickly explained Yahoo, telling him about our metrics and how many people were consuming news online.
Trump stared at me blankly. “What channel are you on?” he asked. “I’m not big on the computer stuff.” The future Twitter president told me he didn’t use email.
The interview never happened.
Surely Hillary will talk to me, I thought; we’d known each other for 25 years. And yet here, too, it was endless calls and emails and dropping by her campaign headquarters in Brooklyn. We got a date on the calendar for February 3rd in New Hampshire—which was promptly canceled, no reason given.
I emailed her campaign chairman, John Podesta, reiterating my desire to talk with Mrs. Clinton. I wrote that I thought she’d benefit from a more relaxed conversation where her warmth and sense of humor could come through—I told him I was interested in “showcasing her personality.” And I shared a social media idea with viral potential called “10 Things You Don’t Know About Hillary Clinton.” Then Podesta’s email was hacked.
The Hillary haters wasted no time dropping bombs in my inbox:
Nice to read your email from Wikileaks. You are a piece of shit. Better sleep with your eyes open. Lucifer
Katie,
You are the most phony, smug, fraudulently deceitful personality I’ve ever suffered through the experience of observing—in any profession. Everything you do to veil the person beneath the perk fails…You are an embarrassment to real Americans. This is how those beyond your circle at Yahoo feel about you. Christian P.
Katie, I just wanted to drop you a note to tell you what vile communist scum I think you are. So happy your television career is over. You always sucked anyway. You are shit just like your pal Hillary.
I googled the scribe behind that last one. He’s a cardiologist in New Jersey. All heart, that guy.
The hassle of changing my email was bad enough. What really frustrated me was how impossible it had been to land the two interviews everyone in media wanted. The Yahoo folks were counting on me to bring in the big names that drove traffic. Particularly Trump, who was the clickiest of clickbait. And I wasn’t delivering.
Marissa, meanwhile, seemed completely unaware. Disengaged. Although in April while covering a stem-cell conference at the Vatican, I do recall thinking that maybe she’d seen the light. Her office had gone to extraordinary lengths to arrange a phone call, factoring in the nine-hour time difference, then letting me know her meeting was running a few minutes long and that she’d reach out the second it wrapped up. I was excited, figuring this had to be big news—maybe a game-changing new partnership with an established streaming service?
Turns out Marissa had two extra seats at her table at the Met Ball a few nights later and wanted to know if John and I could join. Yeesh.
Despite the challenges, I got to do so much at Yahoo. I went to Davos for the World Economic Forum summit and to Moscow to interview Edward Snowden （where I used a burner phone and showered in darkness, terrified the Russians were spying on me）。 I ate hot wings at Harold’s Chicken Shack on Chicago’s South Side with Chance the Rapper; I covered the norm-busting early days of Trump’s reality-show presidency with a top-notch group of Yahoo journalists.
Then, four years in, Tim Armstrong became the new CEO, absorbing Yahoo into Oath （which to me sounded dangerously close to Oaf）。 When the middle-aged mogul started wearing hoodies and hipster stubble and giving virtual pep talks, I knew it was time to go.
And thus ended the Yahoo era. I did a lot and learned a lot （and made a lot）， but I never really felt like our stars were aligned. What I did feel was a bit of an existential crisis coming on.