Last year, when I accepted a job at The Messenger, Jimmy Finkelstein cried.

He called me on an April afternoon and asked what it would finally take to get me to join his news start-up, which was quickly drawing closer to launch day. We’d already had a string of conversations, and I gave him a salary number. I also insisted on severance—four months of it, in case things went south.

“Done!” he replied. He answered so quickly I thought I might have sold myself short.

“I’m so happy,” Jimmy added later, his voice breaking.

I remember staring out my bedroom window, the sun pouring in so strong it was making me squint. I knew I was taking a gamble in accepting a gig at a start-up amid an already saturated news market. So the moment didn’t feel celebratory. Instead I found myself in a what-just-happened haze, like the immediate moments when you wake up from a strange dream. The following day, Jimmy sent me an email asking, “Are we all set. When are u telling Bob?” referring to my boss at the time, Bob Cusack, who serves as the editor in chief of The Hill.

I took three weeks to sign my offer letter, so much so that a woman from human resources finally wrote to say, “I’m so sorry to be a nudge but we can’t begin onboarding without your signed offer letter.” The nudging began weeks earlier when The Messenger’s politics editor texted me the day after I accepted the offer to say, “Jimmy’s worried you haven’t signed.” I told the editor I already knew about his anxiety. Jimmy had already called me twice that day.

Even with an above-grade salary and the cushion of a severance package, the decision to take the job weighed on me. I’m a single mom, who had steady employment for nearly a dozen years at The Hill. That job—working as a political correspondent—saw me through the birth of my son, a relocation, and much of my 30s. It was home, as much as any workplace could ever be.

And Jimmy—whose name would become a regular mention at my dining room table—saw me through many of those years, as the owner of The Hill.

In recent weeks, since The Messenger’s spectacular demise, having reportedly burned through tens of millions of dollars in under a year, Jimmy’s been described as a “sociopath,” selling “snake oil,” and even Boris Karloff–esque.

But at the time, I trusted him. And because I did good work at The Hill, and helped drive traffic, and cowrote best-selling books, he did his best to keep me around.

When competitors tried to lure me away, Jimmy stepped up, always matching their offers. During one of those times, at the height of the pandemic, I was offered a job at another news outlet. And when he caught wind of it from my editors at The Hill, he called me several times and offered to do better.

He was relentless, if nothing else, about keeping me. “I’m not letting you get off the phone until you say yes,” he said on one call.

I said yes.

About two years later, after he sold The Hill to Nexstar for $130 million and began ruminating about his next venture, my phone frequently began to buzz from an unknown caller. And over the course of many months, he would call and tell me about how he was building the best news site, one that would compete with the big guns in media.

Then after the end of February 2023, when he was able to speak freely, he began to make a formalized pitch: He had made The Hill successful. He would do it again, except this time it would be bigger, the pay would be better, the benefits would far exceed what I was receiving. And he would make sure that Martin Luther King Jr. Day and Juneteenth were paid holidays—something that had become a point of contention with my colleagues when Nexstar acquired the company and didn’t offer the days as paid holidays.

He said he needed me to get this project off the ground and he would love it if I joined. I would help build the site, my name would bring instant credibility. At one point, he quipped, “I’m sure Bob will personally come down here and kill me, but that’s okay,” he said, referring to Cusack, The Hill’s editor in chief.

I spent weeks agonizing about it. I talked to colleagues and friends who said I almost had to take the job. After all, I knew the owner, and he had never let me fail. I had hours-long conversations with my parents. I talked to Bob who emphasized the durability and steadiness of my current job.

But mostly, I talked to Jimmy.

“As a single mom, I have no net,” I emphasized on each call with him to the point where even I was tired of hearing it. “If this fails, I have nothing to fall back on.”

During some of those calls, I remember pacing the room, on the outlines of my rug, as if I had been walking an actual tightrope. He was reassuring and had the confidence of a man who never had to worry about the balance in his checking account.

“You will be fine,” he told me again and again. “I will make sure of it.”

When I was having those conversations with Jimmy, I never once thought that the site would implode more than eight months later.

But here we are, and obviously, I am not fine. Neither are the nearly 300 colleagues of mine who lost their jobs in the most cruel and inhumane way imaginable, without warning and without a day of severance. Typically, employers offer COBRA, as a way of keeping your insurance for many months after termination, but ours will be pulled at the end of this month.

Future employers don’t readily have access to our work because the site has been shut down.

For me, it has been the ultimate betrayal.

(Finkelstein did not respond to written questions from Vanity Fair.)

I’m a loyal person by nature and I talked to Jimmy up until the minute we found out about the shutdown from a piece in The New York Times.

I never believed he would ever let us fail. Almost two months before we shuttered, I sat in his bare Washington office that had his name at the door and none of his possessions inside.

My son happened to be with me that day, and he peered out the ninth-floor windows, watching the passing cars on 19th Street in downtown Washington. I sat next to him on a leather couch, adjacent to Jimmy’s desk, and asked for an update.

“Morale is pretty bad,” I told him. “People need to know how we’re doing. They need some peace of mind.”

He picked up his cell phone on the barren desk and dialed up the company’s chief communications officer and asked her to pen a note to staff about our progress.

“The Messenger has grown at a remarkable pace,” came the memo to the staff the following day, spewing numbers like 77 million page views in November.

In that note to staff, he promised more newsletters and events and even Messenger TV. “I remain hugely optimistic about our growth trajectory and am confident in our long-term strategy and ability to achieve our goals.”

Weeks later, when our website disappeared from the web as if it was never there, it felt worse than what I imagine losing a job could feel like. It was this odd mix of emotions, like part break-up, part funeral, as I wrote on X two days after the site went dark.

Oddly, maybe naively, throughout all those chats with Jimmy when he was trying to persuade me to join The Messenger, I didn’t account for the fact that other parts of my life would be hanging by a string. The day before I would be laid off from my job for the first time ever, my car engine completely died, leaving me not only car-less but even more in the hole. Several days later, I would have to cut back on much-needed services for my eight-year-old. We were suddenly in survival mode.

But that wasn’t even the low point. That came when my typically sweet child would have such an intense outburst at school it warranted a call home to figure out what was going on. I had kept the news from him, thinking I had somehow failed him, ashamed to even look him in the eye. But he had figured it out on his own.

“He told us,” his teacher told me.

And my colleagues have been going through similar situations. They’re filing for food stamps and unemployment and counting on a GoFundMe—set up by members of our team—for an extra financial boost. Jimmy recently called that effort “wonderful,” which incensed all of us. Last week, he wrote the staff on our Messenger emails—which many of our colleagues had stopped using—to tell us about how a trustee will oversee the “windup” of the company. It’s a process, he said, that could take weeks or months. No one knows. In the meantime, I joined the class action suit along with many of my colleagues, alleging that The Messenger violated the WARN Act, a labor law that protects employees from mass layoffs with little warning.

Jimmy has also called me twice to tell me to get in touch with two top journalists who could offer me work. When I told him I didn’t need job recommendations, that I needed my severance, he told me he wasn’t able to give it to me.

It was traumatic. And when you’ve experienced trauma—and we all have—you do your best to keep moving forward. And for single parents like myself, there is little time to wallow. (I’ve laughed when well-meaning friends have told me to take off for Tuscany for a week or two.)

But you also try to reflect, and if you’re a journalist by trade, you try to make sense of it all like you would typically do for a reader.

In recounting the shuttering of our site, I heard real stories about its quick demise. Jimmy, for example, called someone on my team and asked for a phone number for Vivek Ramaswamy, the failed presidential candidate, while he was desperately searching for money. There’s another story about how the company sold laptops we used to quickly make some cash.

More than anything I think back to conversations I had together with two of my colleagues, Marc Caputo and Dan Merica, and Jimmy in the final weeks of the young site’s life.

During one Zoom chat, we stared awkwardly up his nostrils as he lay horizontal and called out for someone at his home to bring him “coffee and a cookie” while his dog yapped in the background.

When we had a conference call with Jimmy in early January, the three of us, speaking as representatives for our politics team, wanted to know where things stood after Jimmy claimed repeatedly that the coverage about us running out of money was a lie.

At one point, when Marc asked if our team would remain intact, and wouldn’t have layoffs or pay cuts through at least November—to cover the 2024 presidential election—Jimmy told us he was “88-and-a-half percent” sure that was the case.

But when I asked if the site would shut down, all he could say was, “I’ve never failed.”

“There’s a first time for everything,” Marc replied. And then Jimmy seemed hurt, and somewhat betrayed.

And there was a pause.

“Okay, I could fail,” he replied.

A couple of seconds later, he offered: “If I fail, I fail. I lose a fuckin’ fortune.”