Photos by Nick Coleman.

Photos by Nick Coleman.

Ask Ira Schacter his philosophy on life, practicing law or virtually anything else and he might tell you about a car. One, in particular.

It was a TR-6, a two-seater that British carmaker Triumph Motor Co. built from 1969 to 1976 that’s now considered a collector’s item. Schacter bought it decades ago for just a few hundred dollars. It was only the second vehicle he had owned in his life, and once he restored it from the ground up – a necessity that explains the low purchase price – he had no funds left to replace the aging ragtop.

“So I took the old top, cut it apart and made it into patterns,” recalls Schacter, a partner at New York-based Cadwalader whose practice includes clients in fields from technology to finance. “I took 20 books from the New York Public Library on Fifth Avenue on how to sew, and started practicing.”

In case you’re wondering why he didn’t just go to YouTube, Schacter learned to drive in the 1970s. Public access to the internet didn’t yet exist – much less instructional videos delivered via smartphone. Acquiring new skills was considerably more labor intensive.

Nonetheless, Schacter persevered: “I learned to use a sewing machine, and I sewed a perfectly usable, suitable and ‘looked fine’ convertible top.”

And what’s the message here?

“I look at law the same way,” Schacter says. “Whether it’s mergers and acquisitions or structured finance, or anything in between – you take on challenges, you put in the time and you invent creative ways to make it work.”

He relied on the same philosophy to build his practice after completing a juris doctorate at Nova Southeastern University and his Master of Laws at New York University. Only the ninth member of 230-year-old Cadwalader’s structured finance group when he joined in 1985, Schacter set aside every Sunday night to read about the deals other lawyers were working on.

“I just wanted to know what was out there,” he says. “I had a hunger to know, ‘What are the deals? How do they work?’ This was a very early time in the growth and development of financial products and the like.”

His curiosity paid dividends.

“This is how it would go at Cadwalader in the early days,” Schacter recalls. “A partner would come out of his office, walk down the halls and shout something to the effect of, ‘Goldman Sachs just called, and they want to do this deal that First Boston just did. Does anyone know what they’re talking about?’”

More often than not, Schacter did.

“So after a period of time, they’d more frequently start coming to my office, which meant that I developed a relationship with partners early on, and worked on more interesting, different, one-off kinds of things,” he says.

That approach has allowed Schacter to mature into a holistic strategic adviser over the past three decades – taking roles in transactions from a $21B securitization of franchise agreements for Hilton Hotels to a $325M Series F investment round for cybersecurity firm Cybereason. He recommends the approach to attorneys starting their careers today.

“It’s really, really hard to learn how to be a lawyer working at a law firm, and the reason for that is because you’re adversely selected in your training,” Schacter explains. “Your ability to get good assignments depends on how lucky you are on a day that both you’re more free than your peers and the phone rings with an appropriate client assignment. You have to fill in the gaps by reading and doing homework if you’re going to become a master craftsman.”

Whether it’s mergers and acquisitions or structured finance, or anything in between – you take on challenges, you put in the time and you invent creative ways to make it work.

Schacter, who describes his practice as people-centric rather than product-centric, noticed early in his career that the investment bankers he worked with who were good at their jobs got promoted quickly. “They went from working on the mortgage desk to supervising mortgage securities, then supervising all of structured finance and supervising fixed income,” he says.

Some of the partners at Cadwalader had true relationships with those clients and would adapt to handle whatever legal services the clients needed over time. Others remained focused on their specialties, and when a client was promoted, would transition to working with whomever succeeded him or her.

“I made a very, very conscious decision that I wanted to stay close to the people, because it was much more interesting to me to do whatever they did and to work with them,” he says. “My first love of Cadwalader has always been that it has encouraged its people to find their own path.”

Lawdragon: What made you gravitate, either intuitively or by choice, to people over product? I would have thought, especially at the time, that law firms were emphasizing product. Doing the same thing over and over seems like a more common path to success.

Ira Schacter: Because of who I am, I wanted more breadth. The way I saw it, and still do to this day, you can only succeed to a point by doing the same thing over and over again. You’re never going to grow to run large client relationships and help them in thinking broadly about their business. You may have a great practice, but if you only do the same thing over and over again, there are natural limits to the kind of adviser you can be. Your scope is too narrow.

Plus, I’m convinced – because you see it happening already – that artificial intelligence is much better suited to doing the same things over and over than world-class legal minds. Unless you have skills that allow you to adapt in an ever-changing world, you’re almost by definition running the risk of becoming obsolete in a world that values ingenuity and different things.

LD: Tell me about Cadwalader. Does the culture that attracted you when you were interviewing for the firm still exist?

IS: It does. It does. You may laugh at this story, but it’s one of the things that made my decision in favor of Cadwalader. In those days, firms would take you out to lunch after you spent the day interviewing, and the people who took me out at Cadwalader were two young associates. They were politely sharing food off each other’s plates, which made me feel like they were real people, and that I could work here. I had just gone to lunch the day before with another firm, and the experience felt so stiff. There was something about the people at Cadwalader that just felt incredibly genuine to me.

LD: Did you grow up in New York?

IS: I did, in a town called Merrick, near Jones Beach, maybe 30 miles outside of the city. When you lived there, you got dragged by your parents into the city only to go to museums or buy your clothes, and you only saw the most commercial parts as you went with your dad to his office. So you often missed out on the real rhythm of the city – the really unique things that make this such a special place.

So, not surprisingly, I wasn’t sure about living in New York City. But I remember unpacking the car on that first morning before NYU Law School and thinking to myself, with the action on the sidewalk, that I was never going to leave, that New York City would be my home forever. I love it as much now as I did then. These days, I’m in Red Hook, Brooklyn, close to the office and down the block from my metal shop where I scratch-build cars with raw metal and my bare hands.

LD: I wondered about that after you mentioned rebuilding the Triumph. Do you specialize in any particular kind of vehicles? Where did that interest come from?

If I can give one piece of advice to young lawyers, it would be to not fall into the trap of believing that the precedent is always correct but to have the confidence to forge new frontiers.  

IS: I've been building things since I was 5. I was the kid who took everything apart, no matter what it was – old TVs, old radios, old lawnmowers. Whatever. Then I built ever more audacious, complex things. My first car, which I bought for $75 when I was 15, was a 1966 Buick Riviera that had been in a head-on collision. I spent every minute before school, after football practice and on the weekends fixing it, rebuilding it, having it ready for when I got my license.

In my projects now, I’m very partial to 1930's French Art Deco cars, like the Delahaye and the Bugatti Atlantic and the Talbot-Lago 150. I like the challenge of building something on the outside with that 1930’s look, with a body made of aluminum, built the way they would have by hand in the 1930s, as well as the 200 miles-per-hour sports car performance that could compete with any Ferrari or Lamborghini underneath. I love building my own machines and tools too, not just the car proper.


Of course, it helps to have grown-up kids and a stable career to be able to indulge yourself in things you loved when you were little. It’s both a great release for me, with a very active law practice and great clients who come to me for guidance and, even more so, for my insights on their business and industry. My clients all know about my passion, and tacitly or explicitly, understand the connection. Transactions, like cars, are about forces and opposing forces – the ability to absorb, harness and oppose competing forces whether the horizontal twist from the motor, the forward force from putting power to the wheels, the upward forces of riding over terrain and the cliff-like risk of an unintended impact. Designing around these forces is an art in packaging and the judicious use of triangles. You know you need a motor, four wheels, room for an occupant, gas tank, mufflers, etc. and it all needs to fit into a confined space. The triangle is the strongest yet most elegant shape to oppose and stand up to force. The art is putting it all together in a form that is both functional and beautiful in a Museum of Modern Art sort of way. In a nutshell, this is the fabrication side of building. The other side of building is shaping – the ability to take flat sheets of thin sheet metal and turn it into beautiful shapes like the skin of a body.

Doing deals and providing strategic advice is much the same. I have what I consider my own legal aesthetic, a way I think about deals and risk and business that plays out differently from deal to deal, but is consistent because of how I think about the world and how I think about risk. It all comes back to isolating forces and opposing forces and structuring around them. I tend to think of legal provisions as motivators of good behavior. I’m fortunate to work with some exceptionally talented younger partners and attorneys here, and my team is great. For the most part, when they submit documents, they’re in very good shape. But I tend to think that my job is to go for a walk along the water, close my eyes and think, “If I were the client, what are the eight unique things in this deal that I would need to be protected from and how can I address them?” Inevitably, five of those aren’t in the documents and typical precedents that I’m presented. If I can give one piece of advice to young lawyers, it would be to not fall into the trap of believing that the precedent is always correct but to have the confidence to forge new frontiers.  

LD: It’s interesting how the attitude you have toward your extracurricular projects reflects your professional habits. It’s very versatile. Did that mindset give you or people around you an indication of what your career might be when you were growing up?

IS: I’d say I grew up in a way that would be very indicative. I played football and could talk to the athletes on the teams, but at the same time, I also played guitar in a Southern rock band and could also talk to the musicians. Because I was building a car in my garage, I could talk to other builders who also read the car magazines and worked on their own cars every chance they could. And I could also talk to and befriend the very smart kids. I never found it difficult. I was always able to talk to anyone and everyone. And the secret to my practice, both with the people with whom I work and with the clients with whom I work, is very, very deep relationships.

LD: Tell me more about how your practice evolved from your early work in structured finance to the tremendous range of representations you have now.

IS: Sure. Let me give you an example. About 27 years ago, when I was a baby partner, a senior partner came to me and said, “There's a banker at one of these big banks, a young vice president, and everybody thinks that he is going to go really, really far. He’s not happy with the partner he was assigned to work with and he’s threatening to move his business if we can’t come up with a different one. Would you help?” So, for nearly three decades now, I’ve talked to this person several times a week, sometimes six times a day. He’s now the chief financial officer at a major client. So again, if all I did was the very narrow range of work that he was doing 27 years ago, we probably wouldn’t have grown as much as we have together as friends and colleagues over the past quarter-century.

You can only succeed to a point by doing the same thing over and over again.  Unless you have skills that allow you to adapt in an ever-changing world, you’re almost by definition running the risk of becoming obsolete in a world that values ingenuity.

LD: Interesting. I can see how people have been the consistent factor in your practice. Understanding them and their needs provides a way for you to put your lawyering skills to their highest and best use. It also results in a widely varied practice, which includes things like the naming deal you worked on with Vanderbilt University. Tell me a little about that.

IS: I worked with Goldman Sachs on that as pre-designated investors counsel, meaning that I was hired alongside Goldman Sachs as advisers to the university but would ultimately represent whoever the investors that Goldman Sachs brought in on a series of deals that raised nearly $3B for the university from monetizing the naming rights.

Basically, the Vanderbilt Medical Center on campus has a contract with Vanderbilt University to pay the university for the use of its name, and we sold the right to receive those payments. All of the proceeds went to the university’s endowment fund, and instead of the university taking payments of small amounts for 40 years, a group of insurance companies and other investors paid the university up front and will receive the payments instead, ultimately betting on the credit and the performance of the medical center. It was a very groundbreaking, interesting transaction.

LD: That’s fascinating.

IS: It’s using whole company securitization technology but in a different space, with a different twist and in a different way. The opportunity to do things like that is one of the reasons I like doing deals.

LD: You’ve said you appreciate the way Cadwalader enabled you to take on such a wide range of matters by encouraging lawyers to develop their own practices their way. Is that why you’ve stayed with the firm for so many years?

IS: That, and the beautiful view of the Hudson River and the Statue of Liberty. But, seriously, what makes Cadwalader really special are the people. While I certainly have good friends and good relationships developed here over 37 years, I really believe that the people here are different than at many other firms.

What makes partners successful here and what drives Cadwalader is that we’re entrepreneurial.

It’s a system that gives you a lot of rope to go out and do things, to be yourself. That actually commands the most intensive self-discipline because you don’t want to ask for something, or do something, that causes you not to have what you feel like is unlimited freedom forever. It’s my strong sense from knowing a lot of practitioners that a practice like mine, doing asset-backed securities and mergers and acquisitions, and a lot of other things in between, all at the same time, would be very difficult at another firm. But at Cadwalader, it’s seamless.