[In the] summer of 2008, Sue and I kept up the charade of normal life by hunting for a house. We told ourselves it was optimism. In reality, it was desperation disguised as hope; some fragile belief that this whole FBI informant nightmare had an expiration date.
Sue’s dad, Bob, tipped us off about a new build in Westwood. We drove out one humid afternoon, stepped inside, and immediately saw a future we weren’t sure we deserved: four bedrooms, three and a half baths, wide hall-ways that echoed with the promise of kids’ laughter. A quiet street. Neighbors who waved. A front porch that begged for summer nights and cold drinks. We fell hard for the illusion. And like two people pretending they weren’t standing on a fault line, we made an offer.
The down payment came from our savings and what was left from my last-minute sale of Lehman stock back in May. By Friday, September 12, those same shares were already staggering at $3.65. All weekend we watched the headlines darken: CEOs locked in at the New York Fed on Saturday, emergency calls with the Treasury, frantic rumors of a savior. By Sunday night, the word was out — there would be no rescue.
On Monday, September 15 — the very day we closed — Lehman went to zero.
The entire system was in free fall, and so were we: me, secretly wired up for the FBI, one bad quarter away from being exposed; Sue, fighting to restart a career in the middle of a recession. We didn’t buy that house because it was practical. We bought it because we needed to believe in something.
But belief doesn’t pay a mortgage. The down payment was just the opening move. We needed two incomes to keep the lights on and build the family we pictured standing in that hallway. And deep down, I already knew — no matter how hard I tried to talk myself into staying in finance, there was no future there for me. Not after this. Not after the tapes, the wires, the late-night calls meant to put people in handcuffs. My world forgives greed, forgives recklessness, even forgives crimes. But it never forgives betrayal.
And so, on that day — the day Lehman collapsed into history — we walked out of our attorney’s house with signed papers in hand, clutching the keys to a dream we couldn’t afford and a future we weren’t sure we’d survive.
The Crown Vic was waiting down the block from my office building, just like always. Same spot. Same tinted windows. I slid into the back seat, and before the door even shut, Makol turned toward me.
“Next target.”
That’s how Makol was. No warm-ups, no small talk, no inquiring about how I was doing. Just: “Next target.”
Let’s call Makol’s next target for me Mr. Greenwich, because in every conversation I had with him, he mentioned his house in Greenwich. He was the kind of guy who would stop random people in the street. “You know I live in Greenwich, right?”
I’d interviewed with him while I was at [Blaine Asset Management] and though I didn’t particularly like him, his approach to stock picking had impressed me. I mean, aside from the edge. He had a knack for tuning out the noise, drilling into the key performance metrics that moved a stock, and betting big when others hesitated. He ran a small shop, and he had an uncanny record around earnings announcements. Quarter after quarter, perfect calls. The kind of consistency that should have been impossible.
Again, Makol’s orders were straightforward — reach out, get coffee, same cover story about looking for a seat. “And let him talk!” he spat.
It was just after Labor Day 2008, a time when Wall Street traditionally geared back up. Instead, the markets had pulled the brake and were skidding toward a cliff. The big names were getting hammered — Lehman Brothers, Merrill Lynch, AIG, Morgan Stanley — each one teetering. The S&P had managed a modest uptick in August, but it felt like a sucker’s rally.
Still, at Sedley, Evan and I were positioned better than most, with over 50% in cash. But too many funds were overleveraged, and the subprime mess wasn’t going away. As the market began to shudder, something strange emerged: Small-cap stocks had become absurdly cheap. Not the worthless dot-coms of the last crash — these were real, honest-to-goodness businesses, profitable and stable, trading at multiples of less than two times their net cash. They weren’t even burning money. On paper, it looked like the buying opportunity of a lifetime.
But every time we tried to step in, we got slaughtered. It didn’t matter how solid the fundamentals were — the selling wouldn’t stop. The market had abandoned logic. There was no bottom, no safety net.
Yet through all this chaos, Mr. Greenwich’s three-man shop kept trading like they had a crystal ball. While those playing it straight tried to decode a market that had stopped making sense, Mr. Greenwich seemed to know exactly what was coming.
Walking into the packed Midtown Starbucks, I spotted Makol and Trigg first — two FBI agents trying their hardest to look like they weren’t FBI agents. Makol, at one table, studied the home screen on his phone while Trigg, at another, nursed a cold coffee and stared out into space.
Mr. Greenwich sat in the corner, exactly where they said he’d be. Sporting a golfer’s tan with hair a perfect blend of salt and pepper, he wore a dark blue quarter-zip. As I walked over to him, I manufactured my best hedge-fund-bro smile. Mr. Greenwich looked up as I approached, and I noticed Makol shift slightly in my peripheral vision. I shook his hand and slid into the chair across from him.
“Hey, thanks for meeting up,” I said as I sat down, trying to keep my tone light.
He gave a nod and glanced at the line snaking through the Starbucks. “Place is a zoo.”
“Yeah, no kidding,” I said. “Feels like everyone’s back from the Hamptons and pretending the world’s not falling apart.”
That got the faintest smirk out of him.
I took a sip of the burned coffee I didn’t want and leaned in slightly. “I won’t take up too much of your time. I’m looking for a seat,” I said. The words came out smooth, practiced. Casual. Confident. Believable.
He nodded, waiting for more.
The fact that Mr. Greenwich didn’t immediately brush me off implicated him as an edge trader. With the financial world crumbling around us, legitimate hedge funds weren’t taking meetings with random analysts looking for work. They were battening down the hatches, not expanding their teams. But edge funds operated differently.
These shops had an addiction to information. They needed constant fixes of data that nobody else had, intelligence that could give them just enough advantage to stay ahead of the carnage. Their very survival depended on finding new sources, new angles, new lines to inside data that might translate into profitable trades while everyone else was drowning.
I eased into my script that two FBI agents, seated not far from me, would later pore over every word. I told him about my talent with the whisper number, how I could cut through the noise and get a read on where stocks would really trade after the earnings announcements. How I had built a solid network, guys on the buy-side who trusted my calls. I didn’t outright claim to have edge at first. Instead, I intimated that I was someone who understood how to find edge, how to be around the right conversations.
But then I casually dropped my Moody’s contact into the mix.
“Yeah, one of my guys over there tends to get a feel for private equity deals before they hit the tape,” I said. “He’s been quiet lately — market’s a mess — but last year? Super helpful.”
I let the words hang in the air. I’m getting better at this, I thought. I felt him leaning in.
Then, silence. I had rehearsed this moment. I was supposed to let the silence do the work. But it stretched. And stretched.
And suddenly, this pause became a black hole of awkwardness. Sitting in front of Mr. Greenwich, I started thinking that he was on to me. His eyes were set on mine, peering at me over a slow, deliberate sip of his coffee. I panicked and started babbling about vacation plans. Yes, in September of 2008, as the world’s financial system was collapsing. That was the best I could do.
He checked his phone and said, “I gotta run,” and with that, he was gone.
I got up and walked over to Makol’s table. I slid him the recording device and, without saying a word, turned and walked toward the door.
The next day Makol made his displeasure known. “That was terrible,” he said. “Time to get him on the phone.”
So, I was at it again, dialing the special FBI number that would patch me through.
The phone was easier in some ways — no worried glances, no sweaty handshakes, no awkward silences. But that safety came at a cost. Psychologist Albert Mehrabian found that only about 7% of communication comes from the actual words, with roughly 38% from tone of voice and 55% from body language. On a call, stripped of those cues, I was blind to most of what really mattered.
I dialed the number. A click. A pause. Then the ringtone changed. Mr. Greenwich picked up after two rings.
“Yeah?” he said gruffly.
And as soon as he answered, I heard the second click again. Though faint, it was obvious.
My stomach clenched.
I kept my voice steady. Stick to the script, I reminded myself.
“Hey, thanks for taking my call. I just wanted to follow up on our chat last week.”
“Uh-huh.” Silence.
I pressed forward.
“Look, I know I didn’t explain everything at coffee, but I wanted to be clear — I’m serious about finding a seat. And I know you guys are selective about who you bring in.”
“Yeah.”
“You know, I’ve built some strong relationships over the years. I’ve got a guy at Moody’s who has a good feel for private equity deals before they hit the tape. He was especially helpful last year, and once the markets settle, he’ll have insight again.”
“Right.”
Still nothing.
He was waiting. I had to get him to engage.
“So, like, last quarter — when you guys were dead-on with that Xilinx number … that was impressive.”
Pause. A long pause. Too long. Finally, he spoke.
“Yeah, we’ve got good sources.”
“Right, I figured. So, is that someone inside, or more like a channel check?” A channel check was industry slang — a slightly more sanitized way of saying you’d gathered intel from people adjacent to the company, not direct leaks.
Silence. Everything in my body was telling me I’d pushed too far.
“Why are you asking?” he said.
“Just trying to understand how you guys think about it,” I said. “I mean, I know every fund has a different way of gathering intel, right?” I let out a forced chuckle. “And let’s be real, with the market the way it is right now, it’s not like we can afford to be wrong.”
Another pause.
I wanted to fill it. But this time I didn’t. I just sat there, gripping the phone.
Finally, he sighed. “Yeah. I mean … we have ways. It’s not like these guys come right out and tell you things. You have to know how to read them.”
A guy saying “you have to know how to read them” was essentially admitting there was something to read. That they were getting close to the fire — close enough to feel the heat.
It wasn’t a confession and not illegal on its face. But I knew the subtext. After years as an analyst, you develop an ear for what people aren’t saying. You learn to parse hesitation, deflection, the coded language of the edge. A guy saying “you have to know how to read them” was essentially admitting there was something to read. That they were getting close to the fire — close enough to feel the heat.
Nothing anyone could be arrested for. But enough to keep the FBI listening. I didn’t push further.
“Yeah, totally. That makes sense. Well, look, I’d love to keep in touch, see where things go. If there’s anything I can do on my end, let me know.”
“Yeah, sure.”
I hung up and let out a breath I didn’t even know I was holding. My hands were shaking. I put the BlackBerry down and sat there. Around me, the lobby of 101 Park was alive with the midday shuffle — heels clicking across polished stone, revolving doors sighing open and shut, the echo of laughter from a group of hedge fund bros clutching Chopt bags, and the hum of conversations bouncing off the marble. A courier’s hand truck clattered past, each metallic rattle jarring against my nerves. The scent of burned espresso hung in the air, sharp and acidic, catching at the back of my throat. All of it washed over me like white noise. And yet, there was something close to satisfaction, like I had done the job well.
The thought gave me pause.
This article Inside Wall Street’s 2008 meltdown, through the eyes of an FBI informant is featured on Big Think.