Jonathan Pasternak has spent thirty-six years in bankruptcy and restructuring, most of that time representing the parties on the difficult side of a balance sheet. His practice covers Chapter 11 reorganization, distressed debt, and commercial real estate, and he works in both a legal and an advisory capacity for companies, lenders, investors, and court-appointed fiduciaries.
For more than two decades, he ran his own boutique bankruptcy firm, which grew into one of the busiest Chapter 11 debtor practices in the country by case volume. Running a specialized shop of that size meant carrying a full caseload while also running the business, and he credits that period with teaching him as much about judgment under pressure as any single case did.
His commercial real estate work has always sat alongside the insolvency practice rather than apart from it. Distressed property, debt tied to real estate portfolios, and transactions driven by reorganization all run through the same set of questions: what is the asset actually worth, who has leverage, and what does everyone need in order to say yes.
He has been recognized as a Super Lawyer for more than fifteen consecutive years and was named YJP Professional of the Year in 2017. He is a graduate of The Pingry School, where he finished cum laude in 1981, Brown University, where he studied American History and Literature, and Cardozo School of Law.
Outside the practice, Jonathan is a working musician, well known in the bankruptcy bar for it, and a field recorder of live concerts. He served eleven years on the Board of Trustees of Temple Sinai of Bergen County, coaches youth sports at the recreational and travel levels in Tenafly, and has provided pro bono representation to individuals, small businesses, and local nonprofits throughout his career.
What is your typical day, and how do you make it productive?
I start early, and the first hour is triage. In restructuring, something has always moved overnight: a lender has changed position, a deadline has hardened, a buyer has gotten cold feet. I go through what changed before I touch anything that was already on the list. After that I try to keep court days and drafting days separate, because the thinking each one requires is completely different. The productivity trick, if there is one, is refusing to do serious drafting in twenty-minute gaps between calls.
How do you bring ideas to life?
You start at the exit and work backwards. Every reorganization has an ending that the client can live with, and the job is to identify that ending first and then figure out what has to be true at each step to get there. Most plans fall apart because somebody started at the beginning and hoped. I would rather know on day one what the last conversation looks like and build toward it.
What’s one trend that excites you?
The office-to-residential conversion wave. For years, those buildings were treated as a problem to be refinanced rather than rethought, and now the math is finally forcing people to be creative. It puts real estate, lending, and restructuring in the same room at the same time, which is the part of this work I have always found most interesting.
What is one habit that helps you be productive?
I return calls the same day, without exception. In distress, people are already imagining the worst, and silence from their lawyer fills that space fast. Answering quickly is not just courtesy; it keeps small problems from becoming decisions somebody makes without me.
What advice would you give your younger self?
Slow down before you react. The first version of a client’s story is never the whole story, and the position you take in the first hour is the hardest one to walk back.
Tell us something you believe almost nobody agrees with you on?
That filing is usually a sign of good management, not bad. The companies that end up in Chapter 11 too late are the ones that treated it as an admission of failure rather than a tool. The cheapest restructuring is almost always the one that starts eighteen months before anyone thinks it is necessary.
What is the one thing you repeatedly do and recommend everyone else do?
Read the entire document. Not the summary, not the memo about the document, the document. An enormous amount of what passes for legal strategy is really just someone having read a lease or a loan agreement all the way to the end when the other side did not.
When you feel overwhelmed or unfocused, what do you do?
I pick up a guitar. Music is the one thing I do where the only way through is to be completely present, and twenty minutes of it resets my head better than anything else I have tried.
What is one strategy that has helped you grow your business or advance in your career?
Taking the small cases seriously. Early on, I represented a lot of businesses that no large firm wanted, and I gave those matters the same attention I would give a headline case. Those clients talked. Their accountants talked. That is how a boutique firm ends up with one of the largest Chapter 11 debtor practices in the country by volume, not through any single marquee case but through several hundred people who felt like somebody actually took their problem seriously.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
Getting laid off from my first law job. I felt like I deserved it even though it was due to the economic downturn at the time. From that point on, I honed my legal skills so that I would never face rejection again. 37 years later, I have wholly succeeded in my legal career.
What is one business idea you’re willing to give away to our readers?
A service that helps small landlords and small suppliers navigate a tenant or customer filing for bankruptcy. When a company files, its small creditors usually have no idea what a proof of claim is, what the deadlines are, or that they have any rights at all, and the amounts are too small to justify hiring counsel. Somebody should build the plain language version of that process. The demand is enormous and almost entirely unserved.
What is one piece of software that helps you be productive? How do you use it?
I live and die by Outlook, Google Chrome, and Bestcase bankruptcy software
What is the best $100 you recently spent? What and why?
I made a donation in that approximate amount to my temple so that a friend who was not a member could attend the High Holidays service.
Do you have a favorite book or podcast you’ve gotten a ton of value from and why?
There are too many books to mention, but the Tao Te Ching is a good place to start. I also love the podcast Coast to Coast AM. IFKYK
What’s a movie or series you recently enjoyed and why?
My wife and I love to watch Outlander and Ted Lasso. Song Sug Blue is a great recent film we saw.
Key learnings
- Restructuring work is most effective when it begins well before a company believes it needs help, and the cost of waiting is usually higher than the cost of acting early.
- Planning a reorganization backward from an acceptable outcome produces more durable plans than building one forward from the current crisis.
- Responsiveness matters more in distressed situations than in almost any other area of practice, because silence gets filled with worst-case assumptions.
- Small creditors and small businesses are routinely underserved in bankruptcy proceedings, and there is meaningful unmet demand for plain language guidance in that space.
- A high-volume practice is built through consistent attention to unglamorous matters rather than through individual marquee cases.