• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
Weekly Read

Lehman trader tells (nearly) all

By
Dan Primack
Dan Primack
Down Arrow Button Icon
By
Dan Primack
Dan Primack
Down Arrow Button Icon
September 16, 2011, 9:00 AM ET

Our Weekly Read column features Fortune staffers’ and contributors’ takes on recently published books about the business world and beyond. We’ve invited the entire Fortune family — from our writers and editors to our photo editors and designers — to weigh in on books of their choosing based on their individual tastes or curiosities. Each Friday we feature a different review. This week, on the anniversary of the Lehman Brothers bankruptcy, Fortune.com blogger and Term Sheet editor Dan Primack takes a look at Street Freak: Money and Madness at Lehman Brothers, Jared Dillian’s memoir of his career as a trader at the once-storied firm.

Jared Dillian is a bipolar math whiz whose path to Wall Street led through the Coast Guard rather than the Ivy League. He also is an amusingly caustic writer whose new memoir pulls no punches about a financial career that nearly cost him both his sanity and his life.

Street Freak opens on September 11, 2001, when Dillian was scheduled to begin his first rotation as a trader after graduating from Lehman’s training program. It ends seven years later, when Dillian quits amid the chaos of Lehman’s sudden bankruptcy. But neither bookend gets more than a few pages of attention. Dillian wants us to understand what happened in between.

It’s a bleak story, to be sure. Dillian’s bipolar disorder — not diagnosed until late in the book — leads him to phone-smashing tantrums on the trading floor, alcohol-fueled blackouts after client meetings, and an unsuccessful suicide attempt.

And Lehman’s trading culture seems to feed Dillian’s sickness. The author portrays trading as a manic sprint of decision-making that is part mathematics, part intuition and part speed. Tens of thousands of dollars rest on every click of the button, hundreds and sometimes thousands of times per day.

The reader may not understand all of the mechanics — Dillian sometimes tries to explain them, sometimes not — but the dizzying pace is made palpable by dozens of pages of play-by-play on past trades. It’s an effective technique, albeit one that compelled me to gloss over more than a few sections.

In some cases, Dillian revels in how he outsmarted competitors. For example, he realizes that the market seems to stand still for a couple of seconds whenever major economic data is released. What if he could trade just milliseconds earlier, by sitting with his finger at the ready? It was a strategy that would make millions of dollars for Lehman and help Dillian get promoted, eventually, to the firm’s ETF trading desk.

At other times, however, Dillian makes clear that he only really cared about the money, which represented his standing within Lehman and, ultimately, his level of success. In this he was not alone. Lehman may have considered itself a scrappy team, but in the end, everyone was out for himself at the expense of everyone else. A smaller bonus for you means a bigger bonus for me, which is what I’m here for.

It is a corrosive mindset, and the accompanying pressures eventually became too much for Dillian to handle. In a way, Lehman’s bankruptcy functioned as the author’s personal bailout. Had the bank not collapsed, he might have had a tougher time walking away.

Street Freak’s main failings are twofold. First, Dillian’s wife barely makes a cameo. Here’s a guy whose life changes in momentous ways over a seven-year stretch, but his spouse is completely absent apart from minor pop-ins. Did he leave her out intentionally? Or was Dillian’s marriage more about the official stability than the day-to-day relationship? It’s an odd omission in such a personal book.

Second, it’s not always clear whom Dillian is writing for. Other traders? Lay people trying to better understand Wall Street before the crash? Or himself, as a sort of catharsis, not to mention promotion for the financial newsletter he now runs? The answer seems to change depending on the chapter, which may reflect how Dillian views both himself and the career he left behind.

About the Author
By Dan Primack
See full bioRight Arrow Button Icon

Latest in Features

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Leadership
  • Success
  • Tech
  • Asia
  • Europe
  • Environment
  • Fortune Crypto
  • Health
  • Retail
  • Lifestyle
  • Politics
  • Newsletters
  • Magazine
  • Features
  • Commentary
  • Mpw
  • CEO Initiative
  • Conferences
  • Personal Finance
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Most Popular

placeholder alt text
Success
In 2026, many employers are ditching merit-based pay bumps in favor of ‘peanut butter raises’
By Emma BurleighFebruary 2, 2026
2 days ago
placeholder alt text
Cybersecurity
Top AI leaders are begging people not to use Moltbook, a social media platform for AI agents: It’s a ‘disaster waiting to happen’
By Eva RoytburgFebruary 2, 2026
2 days ago
placeholder alt text
Politics
Meet the Palm Beach billionaire who paid $2 million for a private White House visit with Trump
By Tristan BoveFebruary 3, 2026
1 day ago
placeholder alt text
Investing
Tech stocks go into free fall as it dawns on traders that AI has the ability to cut revenues across the board
By Jim EdwardsFebruary 4, 2026
9 hours ago
placeholder alt text
North America
Gates Foundation doubles down on foreign aid as U.S. government largely withdraws
By Thalia Beaty and The Associated PressFebruary 3, 2026
1 day ago
placeholder alt text
AI
Elon Musk’s SpaceX buys xAI in stunning deal valued at $1.25 trillion ahead of looming IPO
By Amanda GerutFebruary 2, 2026
2 days ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.


Latest in Features

FeaturesBlue Ribbon Companies
Blue Ribbon Companies 2026: See which tech giant made more Fortune lists than any other in the past year
By Fortune EditorsJanuary 15, 2026
20 days ago
Bill Gates and Warren Buffett.
InvestingWarren Buffett
Warren Buffett’s blind spot: Did the digital economy leave him behind?
By Adam SeesselDecember 30, 2025
1 month ago
Photo of Sam Altman
AIOpenAI
Inside OpenAI’s fragile lead in the AI race, and the 8-week ‘code red’ to fend off a resurgent Google
By Jeremy Kahn, Alexei Oreskovic and Lee CliffordDecember 17, 2025
2 months ago
FeaturesThe Boring Company
Two firefighters suffered chemical burns in a Boring Co. tunnel. Then the Nevada Governor’s office got involved, and the penalties disappeared
By Jessica Mathews and Leo SchwartzNovember 12, 2025
3 months ago
CoreWeave executives pose in front of the Nasdaq building on the day of the company's IPO.
AIData centers
Data-center operator CoreWeave is a stock-market darling. Bears see its finances as emblematic of an AI infrastructure bubble
By Jeremy Kahn and Leo SchwartzNovember 8, 2025
3 months ago
Libery Energy's hydraulic fracturing, or frac, spreads are increasingly electrified with natural gas power, a technology now translating to powering data centers.
Energy
AI’s insatiable need for power is driving an unexpected boom in oil-fracking company stocks 
By Jordan BlumOctober 23, 2025
3 months ago