Interview with Tom Kavaler
Tom Kavaler is Senior Counsel at Cahill Gordon & Reindel LLP, a New York-based law firm. He clerked for Judge Milton Pollack of the United States District Court for the Southern District of New York.
Memory and Marginalia
Contents
Max Raskin: Do you prefer to read books on a device or in hard copy?
Tom Kavaler: I have never read a book on a device in my life. That's why God invented hardcover books – so you can read them.
MR: Do you write marginalia?
TK: I believe that is a sacrilege.
MR: Really?
TK: Really.
MR: You don't write in your books?
TK: I do not.
MR: Never?
TK: Never.
MR: That is not what I would've expected.
TK: Here's my theory. I have a pretty good memory. Not a photographic memory like David Boies claims to have, but a good memory. I remember what I need to remember. What I don't remember, I'm not going to remember to go back and look at my marginalia. People write notes, either because they think it helps them to comprehend what they're reading – fair enough – or they think when they go back to look for it, they’ll find it. I'm not going back to look for it. In a general interest book, if I read it, I incorporate into my general store of knowledge that which I retain. That which I don't retain is lost forever.
MR: Are there any writers or books about writing that you read that had an influence? Who taught you or how did you learn how to write?
TK: The answer to the first question is Francis Wellman. There is a book published early last century called The Art of Cross-Examination. The guy was a trial lawyer in New York back in the days before there were big firms, before there was commercial litigation, before there was anything. He's one of these guys that tried all sorts of cases. He wrote a book that I remember now, 50 years later, thinking that it was just an incredibly helpful book.
The answer to the second question is Milton Pollack, for whom I clerked in the Southern District – the greatest trial judge ever to grace the bench in the United States or anywhere else.
MR: I think I clerked for the best trial judge.
TK: Even she would tell you that Milton was better. Milton was phenomenal.
MR: No way.
TK: He was beyond belief. I was his clerk for two years. When he would edit my work, he would go through it with a pencil, and he would just strike stuff out. He wouldn't say anything. He would just strike it out. What he was saying was, “You don't need this.” His favorite expression as to certain verbiage in a brief was, “This is an example of I picked up my pen and, therefore, I wrote.” What he meant was you're not saying anything. You're certainly not persuading me. You're just taking up space. That was in the days before there were page limits and word counts. Today, with a computer, you can do a word count. In those days, it was just his sense that this was unnecessary verbiage. He always said shorter is better. He always said, “If you take more time, you'll be able to write a shorter document.”
The other thing he would do, which again, predates the age of computers – when we were at a late draft of an opinion, it might be 20 or 30 pages, he would lay it out on the floor. He would literally lay out all 30 pages on the floor in four or five rows. Then he would stand over it and he would look down at it. What he was looking for was proportionality. How much space am I devoting to this subject versus how much space am I devoting to that subject? He would see that a certain draft devoted too much space to a subject that was, at best, peripheral. He would shorten that portion of it because he said when you read it, the space devoted to minutiae should not detract from the space devoted to the holding, which was the important thing.
The last thing he taught me on that subject was he would always do a first draft of the facts and his clerks would always do a first draft of the law. He was saying two things: One, it was his take on the facts that was important. He was the judge. Also, he was saying the writing of the facts will drive the train. He was, at that point, in his 70s and he had 50 years of experience writing the facts. I was in my early 20s and I had about two hours experience writing the facts. He was just better at it than I was.
When I'm having a dialogue with the author of the first draft, whether it's an associate or someone else, the phrase I most often use is, “So what? So what?” Look at this sentence. Look at this paragraph and answer this question, “So what? What is our point here? Why are we saying this?” The associate will invariably say, “Well, it's true. It comes from Exhibit 14.” I say, “I'm sure it is true. But who cares?”
Yellow No. 2
MR: Do you have any writing rituals before you write a brief?
TK: I wouldn't call it a ritual, but I immerse myself in all the briefs, and I follow the Paul Masson rule. Paul Masson is a wine company – their slogan used to be, “We will sell no wine before its time.” I create no draft before its time. I think a lot of the problem of extraneous words and subjects is because people start writing before they're ready. I read everything there is to read, then I let it percolate for a couple days. I think about it. I sometimes dictate paragraphs or sentences to myself in my head.
MR: Do you keep notes to yourself on your iPhone or anything?
TK: No, not at all. I'm a very low-tech guy. I just think about it. I sometimes will jot down a few key phrases on a yellow pad.
MR: What kind of pen do you use?
TK: I usually use a razor-sharp number two pencil because I can erase.
MR: What kind of pencil sharpener do you have?
TK: I have a Panasonic electric pencil sharpener on my desk in the office. I have one on my desk in my apartment. I have one on my desk in the country. I'm never more than six inches away from an electric pencil sharpener. I'm constantly sharpening a pencil. I go through boxes of pencils.
MR: What kind of pencil is your favorite?
TK: Yellow number two. I'm sitting here right now in South Carolina at my makeshift desk. This one is a Paper Mate, but I've also used Ticonderogas. My view is yellow pencils are fungible.
MR: How do you feel about mechanical pencils?
TK: They don't maintain a point. They're not sharp. I've tried them because it would be a solution to the pencil sharpener problem.
By the way, I sometimes use number ones. I used to use number ones when I was marking up page proofs from a printer because you have very little space. Number ones are a finer point than number twos, but marking up stuff from the printer is no longer a large part of one's life.
MR: Do you read judicial opinions?
TK: I do, absolutely.
MR: Who are some of your favorite judicial writers?
TK: It has to be Scalia, but second to Scalia is Thomas. If you read Thomas' opinions, they're absolutely brilliant. If somebody tells you Thomas is an idiot or a fool or makes any derogatory comments about his work, it shows that person has never read a single opinion the man wrote. He is a wordsmith. He is a scholar. He is a brilliant thinker, a brilliant organizer, a great writer. His opinions are a pleasure to read. When you read them, you occasionally say to yourself, “I didn't know that. I didn't know that.”
Cohn of Silence
MR: What was Roy Cohn like as a lawyer?
TK: I litigated against him and when I was clerking for Judge Pollack, Roy had two or three criminal cases before Judge Pollack, which were fascinating to watch. One case was brought against Nick Rattenni, known as the Garbage King of Westchester. There were actually two cases. In the first, Rattenni was prosecuted for whatever crime it was, and there was a hung jury or something. The second case was against Rattenni for bribing the jurors in the first case.
During the second trial at lunch one day, Pollack released the jury. They went out. Roy Cohn got up and went out in the hall. Judge Pollack said to me, “Come with me.” We went out in the hall where the elevators are, and we stood back-to-back. Judge Pollack was looking at the jurors. I was looking at Roy Cohn. Over his shoulder, Judge Pollack said to me, “You watch the circus. I'll watch the crowd,” or something like that. His point was if something bad is going to happen, this is where it's going to happen.
My experience litigating against Roy Cohn was the following: You remember the old days, well, you don't. In New York Supreme Court, you used to make your motions returnable in Part One. It was a master calendar part. It was 300 motions a day. The judge on the bench was not the judge assigned to the case. There was no judge assigned to the case. It was a random judge who happened to be sitting that day and he took all comers. All motions that day were addressed by him.
Of the 300 cases on the calendar, 275 would be adjourned or for one reason or another would not be dealt with on the merits. The remaining 25 would be put on for second call. They would be argued by the lawyers who made and opposed the motion that day in the courtroom, right there in front of the judge presiding, who was stone cold – he had not seen the papers before. He might never read them. He would listen to the lawyers for as long as it took him to get some sense of what the case was about. Then he would either say reserved, which meant he was going to take the file back to his chambers and think about it or he would decide it. He would just rule. He would say, "Motion denied." It was the Wild West. It was just unbelievable.
I had several motions with Roy Cohn in those days in that part. I came to the view that Roy's methodology was this: Every judge in that court knew him. They knew him well. They knew who he was. They knew what he was up to and what he stood for. Some liked him. Some disliked him. His bet was that the ones who liked him would rule in his favor regardless. He acknowledged that the ones who didn't like him would rule against him regardless. Therefore, his argument consisted of getting up and saying, “Good morning, your honor, Roy Cohn,” and wait to see what happened.
Over time, over a number of motions, I came to the view that there was some truth to that theory. When you prevailed against him on a particular motion, it wasn't always because of your brilliant cleverness as a lawyer. It wasn't always because of the superiority of your client's facts.
Don’t Go.
MR: You've had to travel a lot as a lawyer.
TK: I'm sitting here with an American Airlines frequent flyer card in my pocket, which says 10 million miles. They sent me a model airplane when I hit 10 million miles.
MR: Do you have any travel tips?
TK: Don't go.
MR: I agree.
TK: Here's my travel tip – it is anathema to people who audit lawyers' fees for a living – people who are a plague upon humanity. You should always fly first class unless you can fly private. The reason is because you can actually get work done. You can't do work in coach because it's unprofessional because whether you're working on a computer or a binder, you can't protect yourself or your work product from the prying eyes of your neighbors left and right. You never know who they are, so the result is you can't work at all.
MR: Do you have a packed bag ready to go always?
TK: I don't have a go bag, but I have a go bag list. I have list handwritten on a piece of cardboard. I have a copy of it at my place in the city and at my place in the country. It says, “Always take this.” It's got such essential things as you were asking about: pencils, highlighters, markers, yellow stickies, sometimes scissors.
MR: Where do you get your suits?
TK: I have them made at Holland & Sherry in London.
MR: Did you always wear suspenders?
TK: At least for 50 years. When I was seven, probably not.
MR: Where do you get your ties from?
TK: Ties come from a variety of places. At one point, my then-secretary had a sister who ran the Bulgari store in Chicago. I was in Chicago one day on business. I dropped in to say hello to her and she sold me 25 Bulgari ties, so for years, I wore Bulgari ties.
MR: Where do you get your suspenders from?
TK: The suspenders are largely from Trafalgar. I always bought themes that were meaningful to me, whether or not my particular audience would always get the joke. Sometimes they had dollar signs on them. Sometimes they had legal themes. Sometimes they had New York City themes. Sometimes they had playing cards.
MR: Do you have a good luck tie?
TK: Actually, I have a bunch of American flag ties in red, blue, green, and yellow. I have maybe two dozen of them because when I get them dirty, they got to go. I wear those frequently in court.
MR: Do you ever get nervous before appearances anymore?
TK: If you don't get nervous, you're not doing it right. But there's a difference between the kind of paralyzing nervousness that causes you to say you can’t go on and the helpful nervousness that asks whether you have all your ducks in a row.
MR: Where do you get your glasses from?
TK: A place on Madison Avenue called Purdy's. I've seen all these ads for Warby Parker and all those other people where you get three pair of glasses for $11 or something. My glasses, which I've been wearing this pair for, pick a number, 15 years, cost $2,000 or $3,000 because they're Varilux, they’re multi blah blah…who knows what they are, but they last forever. Whenever these eye pads wear out or the ear pieces, you go into Purdy's, and they replace them. They tighten them up no charge. I've got sunglasses from Purdy's. I've got skiing goggles from Purdy's. My son has skiing goggles from Purdy's.
MR: Where is your favorite restaurant?
TK: Sistina on 81st Street between Madison and Fifth, across the street from Campbell's Funeral Parlor. Best Italian restaurant in New York.
MR: What's your favorite thing to eat there?
TK: My favorite dish there that I have as an extra course is whatever pasta of the day strikes me with white truffles. Restaurants always tell you it's truffle season. My guess is it's truffle season somewhere in the world every day of the year.
MR: Where’s your favorite place for a slice?
TK: I'm heartbroken because all the dollar pizza places have now gone to $1.50 or something. The best pizza in New York to run in and run out – I’m not talking about a sit-down restaurant where you have an esoteric pizza – is a dollar pizza place on Lexington right outside Davis Polk.
MR: If you want to have a drink with a good friend you pick the place, where are you going?
TK: I can invite them to my house.
Scotch War Crimes
MR: What’s your favorite thing to drink right now?
TK: Macallan 25, the anniversary edition. It's a great single malt scotch. It's very smooth, very satisfying.
MR: How do you drink it? Do you put a little bit of water in it?
TK: That's a war crime, Max. You should be arrested for that.
MR: Just a little bit of cold water.
TK: I know the theory. It's crap. Good scotch should be drunk neat.
MR: What about wine? What's your favorite wine right now?
TK: I'm working my way through the last of the '82 Bordeaux. I bought cases and cases and cases of '82 Bordeaux as futures in '81 or '82. They were delivered two or three years later. I cellared all of them and I've been drinking them the last few years. Unfortunately, I've drunk so many I'm running out. We just had, for Christmas, an '82 Latour. It was spectacular.
MR: My dad has this funny joke. Have you ever been to Bern's Steakhouse in Tampa?
TK: Actually, I have – they have a great wine list.
MR: So a few years ago I went there and I called my dad after to brag about a wine my friend ordered from 1955. I asked if he ever had wine from 1955. He says, “I was born in the 40s…all the wine I drank was from 1955.”
TK: Good point. I know your dad. I know he's a very funny guy.
Globetrotter
MR: Who is the person in your life that you've had the longest friendship with that you still spend time with?
TK: I went to third grade with a guy, and we went through school together. We remain lifelong friends. Then he went out to the West Coast and did what people do on the West Coast. Eventually, that ran out right around the time that Loretta and I were building our house in Garrison. It occurred to us that we would need a full-time, live-in caretaker to live in an apartment that we built over the garage. At that point, he had fallen on hard times, and I was, basically, subsidizing him. I thought to myself why don't I bring him back east and install him over the garage instead of sending him checks every once in a while so he doesn't eat cat food in the winter? I'll just pay him a salary. I brought him back and put him over the garage and he was our caretaker for the next 35 years.
MR: What's your favorite trip you've ever taken?
TK: It would be one of a couple. We went on a safari in Africa, which was just spectacular. It was great.
MR: Which country?
TK: Kruger Game Preserve, which is in the northeast of corner of South Africa, I think. We stayed at a place called MalaMala, which is a great resort. That's one. Another one was we took a raft trip down the Colorado River through the Grand Canyon with our children. That was great. That was just great. The third one was we rented a private boat in Alaska. We went from Juneau to Sitka, took a week, and we sightseed along the way. Those were the three best trips ever in the history of humanity.
MR: What kind of shoes do you wear?
TK: I'm not one of those John Lobb people. I'm not a shoe fanatic. I wear whatever shoes are in my closet. Some of them are Allen Edmonds and some of them are Cole Haan. It depends if they're lace-up dress shoes or loafers, but a lot of times, it's nothing more than we go to Woodbury Commons on the weekend and while she's shopping, I buy shoes.
MR: Would you ever live somewhere other than New York City?
TK: Never. I’d have to have someplace better to go. Where would that be?
MR: Boca.
TK: Florida is the land of the living dead – God's waiting room. The alligators can have it. We once landed in Jacksonville. The air in the plane on the way down had been perfect airplane air. It was air conditioned. It was filtered. It was fine. As the door opened and the Florida air came floating back into the cabin, I almost couldn't breathe. It was like trying to suck pea soup into your lungs. It was disgusting. Florida is the armpit of the universe.
MR: Who's the best mayor in your lifetime and who's the worst?
TK: The worst is de Blasio, without question. The best is Bloomberg.
MR: What do you remember about Ed Koch?
TK: In fairness, I shouldn't slight Koch. Koch was terrific. I think Koch and Bloomberg are great. Rudy was a very mixed bag. He had a few good weeks after 9/11, but before that, he was no great shakes. Dinkins was terrible, and I always thought nobody could be worse than Dinkins, but de Blasio retired the trophy.
MR: Where were you on 9/11?
TK: I was on the 87th floor of the Empire State Building. I sit on the board of the Greater New York Councils of the Boy Scouts of America. I'm on the finance committee. For years, we used to have the finance committee meetings on Tuesday mornings at Deloitte & Touche on the 102nd floor at the World Trade Center. Had we not moved the meeting, we would've been sitting right there where the plane impacted. For whatever reason, the month before, we had decided to move the meetings. The Boy Scouts had moved to a new office on the 87th floor of the Empire State Building. We decided to hold the meetings there with the result that we could see the Trade Center on fire, but we weren't in the Trade Center. I remember it distinctly.
Then I went downstairs, and I got a cab. I told the guy to go downtown to the courthouse to pick up Loretta. At first, he didn't want to go. He said, "Downtown's on fire." I said, "That’s on the west side. We're going to the east side." He got off the drive at South Street and there's a cop standing there. He said, "What are you doing?" I said, "I'm going to pick somebody up at the courthouse." He said, "Are you out of your mind? Turn this cab around. Fill it up with five people and get the hell back uptown." I did and when I got to the house, there she was.
Aaron Sorkin, Top Gun
MR: When you talk about how corporate New York operated back then, it sounds like Mad Men. Did you watch the show?
TK: I watched every episode. I loved it. It was a great show. It was really well done.
MR: It's one of my favorite shows.
TK: Me too. I don't think anything about my life was Mad Men-ish. Maybe that's my loss. Maybe it would've been aspirational, but I'm not in a position to say whether that was or was not an accurate reflection of the advertising business. I'm sure there's no widespread drinking in law firms today. That was just not true.
MR: What are some of your favorite TV shows?
TK: Before the pandemic, we almost never watched TV at all. Since the pandemic, we have become habitués of the streaming world. We really liked Downton Abbey. We liked Madam Secretary. We watched all of The West Wing, which we'd never seen before. We also watched House of Cards.
MR: Who was your favorite character on The West Wing?
TK: I got to say even though he's obviously a communist, the president. He had good lines.
Here's what I'll tell you. The West Wing was as good as it was because it was written by Aaron Sorkin. A Few Good Men is as good as it is because it was written by Aaron Sorkin. I don't know if you've seen it yet, but there's a new movie out called Being the Ricardos – we watched it. It is spectacular. Written by Aaron Sorkin. But it's not a fair fight. If you've got a movie written by Aaron Sorkin competing with a movie not written by Aaron Sorkin, the guy who is not Aaron Sorkin is going to lose.
MR: What about old movies? What are some of your favorite movies?
TK: Top Gun is a great movie. Then, of course, there's the greatest movie ever made in the history of the human race, Animal House.
You sometimes watch some of these old movies on TCM and I always ask myself what was the attraction? I don't get it. Some of the old John Wayne movies, the Marilyn Monroe movies – the dialogue is horrible.
MR: Some of them hold up and some of them don't.
TK: Exactly. Stagecoach, supposedly one of the greatest movies ever made, I don't get it. I don't know why it's the greatest movie.
Jimmy the Weasel
MR: Are you a Goodfellas fan?
TK: I like all of those mob movies. Martin Scorsese does a good job. The Godfather series was terrific. I don't know what this is emblematic of, but more people quote lines from The Godfather probably than any other movie in the history of the universe. My favorite line is Hyman Roth’s, “This is the business we have chosen.” I use that all the time. When some associate complains about having to do something on a short schedule because some judge arbitrarily says something…
MR: Did you ever run into Meyer Lansky?
TK: Never, but I did, in the Newton case, take the deposition of Guido Penosi, who was a big time Mafia figure in Las Vegas and a guy in Bridgeport, Connecticut, Frank Piccolo. I also interviewed on a boat in the Potomac, under the watchful eyes of the US Marshall Service carrying submachine guns, a guy named Jimmy the Weasel Fratianno.
MR: Moving that meeting before 9/11 – do you believe in providence?
TK: Certainly not providence, except if you're looking for a place to eat in Rhode Island. Karma, do I believe in karma? I don't know if I believe in anything, Max. I think sometimes shit happens.
MR: Do you believe in God?
TK: No, absolutely not.
MR: Do you believe in an afterlife?
TK: No.
MR: You never believed in God?
TK: No.
MR: Were you brought up religious?
TK: Nope.
MR: Were you a fan of the Brooklyn Dodgers?
TK: Actually, I was, but it was very strange. When I was a little kid, we had a cleaning lady who came in one day a week and cleaned. Her name was Belle. I liked her a lot. She was funny. She was cute. She talked to me, which no one else did. She was from Brooklyn. The only thing I knew about baseball was that there was a team out there called the Brooklyn Dodgers, of which she was a fan. So I figured if she was a fan, I was a fan. Then, at some point, I lost contact with her and I lost contact with the Dodgers, and they were so upset about this that they moved to California.
From Cabs to Bordeaux
MR: I want to ask you about cab driving. Would you have thought when you were driving a cab that you would end up where you are now?
TK: Not only would I never have thought it, I can see as clear as day, the day in 2L year that my friend Jim Brown and I said to each other, “If you could ever make $25,000 a year, you would be pig rich. You could own a Mercedes. Can you imagine making $25,000 a year?”
MR: When did you drive the cab?
TK: I drove the cab in college and in law school. The deal in those days was you got a hack license from the New York City Police Department, which, by the way, I have framed sitting on a shelf in my study at home. Then you go to a fleet, and you would register your license with them. You could go in whenever you wanted and pick up a cab for a shift because there were always more vehicles than drivers. In those years, I would go in on Saturday nights. A Saturday night shift was 4:00 p.m. to 4:00 a.m. Usually, on one Saturday night shift, you could make $50. In those days, $50 would keep you in beer for the entire week. You would work one night and make enough money to pay for beer for the entire week.
One summer, I guess my 1L summer, I couldn't get a law job, at least at the outset, so I thought I'd drive days. I went into the garage, and I picked up my cab and I went out. The first day, I think I made $4 because you couldn't move. You were stuck in traffic. It was the stupidest idea I ever had in my life. After the second day, I put the cab back and I went and got a job at MFY Legal Services, which didn't pay anything, but I figured it was better than driving a cab.
I used to drive the cab at nights, and I was always looking for the perfect passenger – somebody who wanted to go somewhere in Manhattan that I could find and who looked like a big tipper. One night, I'm coming up Madison Avenue. It must've been 10:30 or 11:00 on Saturday night. I see this guy standing there with his arm up. He's got a very nice, luxurious overcoat with these fancy fur lapels. He's clearly wearing a fancy suit. He's got spit-shined shoes. He's wearing a Homburg and he's carrying a briefcase. I figured this is it. This is the guy I've been looking for. He's not going far, and he'll be a generous tipper.
I pick him up and, sure enough, we're going somewhere on upper Park Avenue. We're driving along and we're chatting. He says to me, “It's clear from your conversation that you're not a real cab driver. You must be a student.” I said, “I am.” He said, "Where do you go to school?" I said, "Well, actually, I'm in law school." He said, "Oh, that's interesting." He said, "And what are your plans and hopes for your career?" I said, "Well, I'm not sure yet, but I hope that whatever it is, I won't be working on Saturday night 11:00 like I am now." He sighed and he said, "Well," he said, "I think you're going to be disappointed." He said, "I'm a lawyer. You just picked me up outside my office. I'm going home. It's Saturday night. It's not unusual." I never forgot him.
Frankfurt-on-Hudson
MR: What is your family’s heritage?
TK: They were from Vienna.
MR: Both your parents were Jewish?
TK: Correct.
MR: And neither of them was religious?
TK: They were the kind of religious that they would go to the synagogue on the high holidays.
MR: What about their parents?
TK: I have no idea.
MR: Were you ever intrigued by Israel by moving to Israel?
TK: Moving there, zero interest. Politically, I'm a big fan of Israel. I think they're a staunch ally, the only country in the Middle East that has any commonality with us. I think we should support them very strongly.
I have friends who have gone there multiple times and when you ask them what’s the attraction, they say it's the homeland of the Jews. I don't get that at all. If you said to me the beaches are great or they have fantastic restaurants or there's a mountain that you climb and you can see Cleveland, okay, but that doesn't make any sense to me. I should go there because it's the historic homeland of the Jews?
MR: Is your Jewish identity important?
TK: Zero. I think of myself as a Republican.
MR: What's the last full album, music album that you listened to?
TK: Well, you have to understand that on the weekends in the country, it's usually Neil Diamond wall to wall, 24/7. The other thing we listen to a lot at home is the soundtrack from Jersey Boys.
MR: Do you floss?
TK: Not as often as my dentist wants me to. I pick. You know the pick that goes between your teeth? I pick more than I floss.
MR: Do you use an electric or a mechanical toothbrush?
TK: Mechanical.
MR: Hard bristles or soft?
TK: Whatever is in the bathroom.
MR: What kind of toothpaste do you use?
TK: Crest.
MR: Yeah. Do you wear cologne?
TK: No.
MR: Where in Brooklyn are you from?
TK: I'm not from Brooklyn. I was born and raised in Washington Heights, uptown Manhattan. I lived in a house that was less than two blocks from the house where Henry Kissinger grew up.
MR: That's where all the German Jews lived.
TK: That's exactly right.
MR: The Yekkes.
TK: It was known as Frankfurt-on-the-Hudson.
MR: Did you go to Breuer's shul?
TK: No. I went to P.S. 187.
MR: No, not the school, the shul.
TK: P.S. 187.