Q. You went to the University of Kansas for undergrad. Kansas! What made a dyed-in-the-wool liberal want to study in the evolution-denyin’, criminal-fryin’ middle of the Midwest? Are the stereotypes true? Was it fun, a walk on the wild side? Or were you desperate to get out? You majored in history, but switched to painting midway through your degree. Were you going to be the next Caravaggio? Gauguin? Or Kusama Yayoi? Did you have an inkling you were going to end up as a lawyer?
A. I was born in Dodge City, Kansas, which is famous as the former “Sodom of the West” and the setting for Gunsmoke. By the time I came along it was really just a Wal-Mart and lots and lots of churches.
People who grow up in the rural center of the United States invariably fall into one of two broad categories: People who think climate change is a hoax perpetrated by the gay illuminati in an effort to disarm the populace so that our overlords in the New World Order can enforce Sharia law; or People who desperately want to live anywhere else. I think I was maybe three by the time I realized that I was in the latter category.
I don’t want to unfairly malign my home state too much or make unfair generalizations (primarily because I have a lot of family back there), but at the same time, most Kansans are too polite to say anything back to me so I can probably go even further. Growing up there was a bit like being raised in a cult. There is an appropriate way that everything must be done, but everyone is super nice about it. The food also sucks.
When I went to college, I wanted to get the hell out of Dodge, so to speak, but only made it as far as Lawrence before my money ran out. Probably because I was always an oppositional pain in the ass, everyone I knew always assumed I would become a lawyer. In order to defy that expectation I decided to be an artist instead. I even took it further and decided to make the most unpopular style of art I could think of – workmanlike and technically proficient history paintings. I can’t say I was necessarily very good, but I was very oppositional. So there’s that.
Q. After undergrad, you and your wife emigrated to Philadelphia. Your wife, an art historian, went to Temple for grad school, while you applied and got into the Pennsylvania Academy of Fine Arts. Was the plan to work on your brush technique, or did you mean to sell out and become an academic? Are you ever glad you dodged that fate, given that today’s academics are either petrified of the militant children they teach or enthusiastic participants in the madness?
You stuck it out for exactly a year before you decided the artist’s life wasn’t for you. What was the straw that broke the camel’s back? What did your wife think? Back then, where was Caleb Kruckenberg headed?
A. My wife is another native Kansan who was desperate to escape. So after college, we were both game to flee to anywhere.
We ended up in Philadelphia basically on a whim, as that was the only city where we both were accepted to respective graduate programs.
Our plan was to both be academics. We would be poor and drink crappy red wine and engage in revolutionary politics. I would make deeply unpopular and extremely boring paintings of heroic nudes standing in contrapposto in my spare time while I taught my students the difference between an “H” and “B” pencil.
What no one ever shared with me (or at least no one I respected), is that essentially nobody becomes an academic anymore. The whole generation of bearded abstract expressionists with tenure is being replaced by armies of adjuncts with MFAs who primarily work at Trader Joes. And you have to really want it to make it past all those interviews at Trader Joes.
I eventually got really into the aggressive antagonism of Paul McCarthy (not the Beatle, but “Captain Ballsack”). Once I started down that road, I eventually concluded that the most oppositional thing I could do was to drop out and become a lawyer.
So between my bleak economic future and what I convinced myself was actually a very square sort of rebellion, I fulfilled my legal destiny.
Q. After PAFA, you took a volunteer internship with the Philly DA’s office. Why law? Why crimlaw? And what made you want to join the dark side and throw in with the prosecutors? What did you help them with? It seems they made a good impression, because you applied to law school while you were still working there. Was the plan to become one of them as soon as you passed the bar? Or did all the horrors you saw committed at the DA’s office convince you to join #TheResistance?
A. There is a show on A&E called the “First 48.” It’s a true crime show that follows homicide detectives around for the first 48 hours after a murder as they try to solve the case.
When I left PAFA, I was obsessed with it. My wife was working on her Ph.D., and we didn’t have any kids. So when I wasn’t working at my dumb part-time jobs, I just sat around my apartment in my underwear watching that show.
I think what drew me to that show was a fascination with people doing genuinely important work. There’s very little apparent moral ambiguity in solving murders – it’s an unqualified good and important thing that should be done.
It occurred to me that I could be a participant. While I didn’t necessarily want to be a police officer, I figured prosecution would be a good move. On a whim, I called the DA’s office and asked if they wanted an unpaid intern with a useless college degree. Like all government agencies, they said yes when they heard the word “unpaid” and let me join.
The DA’s office was great. I got assigned to a bureau that handled a lot of violent crimes and I was involved in witness meetings and spent a lot of time in court watching shit go down. It was really exciting, and the prosecutors I worked with were dedicated and genuinely cared about their work. I also fell in love with the culture. Growing up in Kansas I had never thought it possible to hear people in nice clothes say “fuck” all the time while they were at work. It felt like I was helping with important work, and also like I was part of a special club of people who gobbled Tums and barely slept while they held society together.
Q. You went to Temple Law, graduating in 2010. That was one of the toughest markets for baby lawyers in recent memory, and a lot of dreams of six-figure Biglaw salaries were crushed when you and your cohort hit the streets in search of a job. How’d you fare? Was there anything you wanted to do and were denied, or did you make a beeline for the Manhattan DA’s office? Did you disappoint your pals in Philly by not signing on with them? At that point in time, would you have considered defense?
A. During law school I just assumed I would join the Philly DA when I graduated.
I didn’t plan, however, on the economic collapse and the fact that every public agency in Philadelphia, including the DA’s office, would go into a hiring freeze. But they did, and I realized that my economic prospects in Philly were about as good as they had been when I was in art school.
For some reason all the DA’s offices, but none of the public defense organizations, in New York City were hiring. I interviewed with all of them, and was lucky enough to get a job in Manhattan.
From the perspective of someone who came to the law from watching television, this was an ideal placement. I mean, you may or may not be aware, but there has been at least one television show about the Manhattan DA’s office.
Q. As a newly minted Manhattan ADA, you were dispatched to the ever-unpopular Appeals Bureau, where, rumor has it, you had a fistfight with another prosecutor over legendary appeals chief Mark Dwyer’s old chair. Was it actually a fistfight? And did you win? How’d you end up with that assignment? Did you have to be “nudged,” given that most prosecutors prefer standing in the well to writing briefs all day? Or did you volunteer?
A. My rookie class at DANY was something like 100 lawyers. Of those, I would say one genuinely wanted to be placed in the Appeals Bureau. Everyone else was gunning for a trial assignment. Which makes sense, considering I wasn’t the only rookie ADA drawn to service by television.
I had worked for a Pennsylvania Supreme Court Justice during law school, which flagged my resume for a possible appeals spot. During the interview process, ADAs from Appeals kept showing up on my interview panels and asked me questions about preservation and standards of review. Once I got the job offer, the writing was on the wall about where I would end up.
I was officially asked to request an assignment, but I was worried, perhaps unreasonably, that they might pull my job offer if I asked for anything other than Appeals. So I did, and, shockingly, that was where they put me.
In the end it was a really good assignment. I handled more than 100 cases on appeal while I was there, which meant that I basically dissected all of those cases from start to finish. Doing that kind of post-mortem is a great way to understand the legal issues – what works and doesn’t work, and even the mundane process of litigating a case.
I came into DANY at a time of change. Robert Morgenthau retired the year before I joined after about 250 years in the position. The longtime Appeals Bureau chief Mark Dwyer also stepped down to join the bench at about the same time. When I showed up at the office, it was like the whole office was trying to learn how to manage in a totally new world.
Aside from prestige, DANY is remarkable in the shabbiness of its office space. After a few years at the office, ADAs can expect to move up to shared offices, and may even get a few select pieces of furniture that still function as they were originally intended.
One of my greatest triumphs at DANY was capitalizing on the uncertainty in the office in 2010 to acquire Mark Dwyer’s former desk chair. Through a series of elaborate trades, I was able to transition from my original non-reclining, heavily stained and cracked chair to Mark’s decades-old thousand-pound monstrosity. The chair was definitely no more comfortable than anyone else’s, but it was a pure power move to end up with it. I miss it.
Were you one of those appeals prosecutors who mailed it in, change the names around in the same old brief and called it a day? Or did you only put your pen to bespoke work? Were the periodic appearances before the NY Supreme Court’s Appellate Division something you relished, or did you long for the security of your desk?
I hate form briefs. I hate “boilerplate” sections. I hate being told not to “reinvent the wheel.” Because criminal appeals generally involve a few narrow classes of related issues in hundreds of different cases, there is a strong incentive to rely on what has worked before. As a government agency, moreover, the DA’s office wants to have a unified stance on cases and issues, and so leans even more heavily on what has come before.
I butted heads with my superiors all the time about wanting to do things my own way. I convinced myself at the time that it was about doing things better than they had been done before. In hindsight, a lot of that was unqualified egotism.
Regardless, I put a lot into my work at the DA’s office, and I stand behind everything I wrote.
I liked appellate work. (I still do.) But by nature I am a courtroom attorney. I adored oral arguments, and took every opportunity I could to appear before the Appellate Division. Not only was it fun to appear before a panel of five judges, but the courtroom is unbelievable. I have practiced law all over the country and been in lots of courthouses, but nothing compares to the Appellate Division, First Department in opulence.
Q. Prosecutors rarely lose an appeal in New York’s First Judicial Department. What about you? Ever lose one? If yes, did you deserve to lose it? Conversely, did you ever win one you really wish you hadn’t?
Ever been the appellant? If so, how’d you do? And was cleaning up a trial prosecutor’s mess an interesting change of pace?
You were good at your job. (Obviously; we only take the best at Fault Lines.) But be honest: was your success rate due to your mad appellate skillz, or do you think you’d have fared differently if you hadn’t been wearing the white hat?
A. In about 100 appellate cases, I lost 3. For an appellate prosecutor, that’s actually a pretty lousy appellate record. We were supposed to win every case.
One case that I was proud to lose was People v. McGann. This was a case where my office had prosecuted a homeless man for sleeping on the sidewalk. We used a “quality of life” ordinance that was originally meant to stop the scourge of abandoned cars on the streets of New York that Mayor Giuliani dug up and repurposed to criminalize homelessness to arrest the defendant when he refused to go to a homeless shelter. Instead of doing what most people do and simply plead guilty in exchange for an ACD (Adjournment in Contemplation of Dismissal) at his first appearance, the defendant had called bullshit and fought against us all the way. He was right to do that, and I’m glad he won.
The one case that I won that I wish I hadn’t was People v. McCray. Like most states, in New York residential burglary is more serious than non-residential. What makes a building residential is that it has a home or rooming house attached to it. In New York City, basically everything qualifies as a residence, and it is up to individual prosecutors to use their sound discretion to charge residential burglary where appropriate.
This defendant had burglarized Madame Tussaud’s Wax Museum in Times Square, but he had been charged and convicted with residential burglary because the Hilton Hotel sits on top of the same massive building that houses the museum. I defended the case on appeal and the Court of Appeals eventually affirmed that, yes, the museum was a “residence,” no matter how unfair that might seem.
Q. You underwent a radical career change in 2013 when you left the DA’s office to become a New Mexico State public defender. Why’d you hang up your prosecutor spurs? And why New Mexico? You left Manhattan in November; didn’t you worry you were going to miss NYC’s refreshingly brisk winters? Was it difficult for you to break out of the prosecutor’s mindset, switch from putting people behind bars to fighting to keep them free? Other former prosecutors who’ve done what you did report a change in empathy toward criminal defendants. Did you have to do some recalculating, or did you know exactly what you were getting yourself into?
A. While I was originally attracted to prosecution because I wanted to do something important to help people, the reality is that most criminal charges are not about individual redress but maintaining social order. Abstractly, drug crimes have victims, often the defendant himself. But, after a while, it is hard to get motivated about making sure a drug dealer, or user, stays in prison. After three years as a prosecutor, I had had enough and decided to go to defense.
Of course, when you spend years being gung ho about prosecution, it’s hard to convince public defense organizations that you are on their side.
On a whim, I applied for a job at the New Mexico State Public Defender. They paid well and would accept my out-of-state law license, and my wife and I were both sick of New York City. I didn’t really think anything would come of it.
I interviewed on a Thursday, and had a job offer the next day. I put in my notice the following Monday and got out of New York just as the really crappy weather was setting in.
Q. The New Mexico public defender made you a felony trial attorney right off the bat, about as far from appellate work as it’s possible to get. Was that a deliberate decision? You thrived on the work, even though you were suddenly playing for the other team, in a different, especially high-pressure role, and managing a PD’s caseload – over 100 cases at any given time. How’d you do it? And how’d you adjust to the different culture of a PD’s office? The lack of resources, the incredible demands on your time, the stark realities of representing the indigent and underserved? Did you find that judges treated you with suspicion where they used to laugh at your jokes? Ever think to yourself, “I should’ve stayed in 1 Hogan Place?”
A. One of the big selling points for me at the PD’s office is that they agreed to make me a felony trial assistant. I always wanted to try cases and they gave me the chance right away. When I got there on my first day, I had a huge stack of files assigned to me, and my supervisor basically just told me “good luck.”
I loved that job. My first trial was a first-degree murder case that I tried with another lawyer who had also just started at the office. We got a not-guilty verdict and I was absolutely hooked on trial work.
Q. One year into your job with the state of New Mexico, you were poached by the federal public defender. Suddenly, you were no longer facing run-of-the-mill prosecutors backed up by local and state cops, but the feds, with nearly unlimited resources at their disposal and a nasty habit of building their case for years before bringing them to trial. Was it a very different assignment from being a state PD? How do federal public defenders’ offices differ in their approach?
You continued your hot streak at trial, but you also went back to doing appeals. Was it like a homecoming, or did your year of standing in the well leave you feeling like you were warming the bench?
Speaking of which, it’s finally time for the obligatory first trial question. What was your first trial as a federal defender like? Whom were you representing? What were you up against? Going in, did you believe you had the win in the bag? And were you right?
A. The best thing about practicing in a small legal community is that it is easy to quickly build a reputation. I had a few pretty big wins at the PD’s office, and was able to finagle that into a spot with the federal defender after just a year in New Mexico.
Federal practice was a whole different animal though. In state practice you can often win cases just because the police and prosecutors are overwhelmed. Stuff falls through the cracks.
That doesn’t happen in federal court. I once had a client who was caught on video by a drone selling machine guns to the ATF. That’s not a case you can win by attrition.
Still, there are opportunities to fight federal cases – you just have to be enterprising.
One of the most far-reaching victories I’ve ever had, in any setting, was a case that seemed hopeless. I had a client charged with re-entry after removal, which is basically the crime of returning to the U.S. after you’ve been deported. If a person has a criminal history, then he is guaranteed prison time. My client had previously been convicted of a federal drug conspiracy, which was based on his act of carrying a backpack of marijuana into the U.S. from Mexico, for which he had been sentenced to 90 days in jail and deported. He returned again, and this time was looking at several years in prison.
I made a very technical argument that his conspiracy conviction should not be counted as a “drug trafficking offense” under the sentencing guidelines, and he should only face about a year in jail.
I lost at the trial level, but won on appeal, and, in the process, created a circuit split. Maybe most significantly, that decision applies to lots of different parts of the sentencing guidelines, and has potentially saved a very large number of people from having sentencing enhancements applied to them.
As far as trial, my happiest moment came when a jury found one of my clients not guilty after he was arrested with approximately 7 pounds of cocaine hidden in a car he was driving when he came across the border. My client was a young father from Mexico who had been recruited by a family member to buy construction materials in the United States. My client didn’t know that his family member had arranged to have drugs hidden in his vehicle. So-called “blind mules” are actually fairly common at the border, but that doesn’t really stop the government from prosecuting them. Fortunately the jury was able to overcome what might have seemed like the implausibility of the defense, and found him not guilty. Instead of serving a mandatory five-year prison sentence, he went home to his wife and kids.
Q. Last year, shortly before you joined Fault Lines, you went back to Philly to become a senior associate at Levin & Zeiger LLP, where you handle criminal defense (especially post-conviction) work and represent clients in civil-rights actions against the government. How’d you get the offer? What made you decide to take the job? After a lifetime of cashing the taxpayer’s checks, was it a shock to join the private sector, become a working stiff like everyone else? Have you come full circle? Is there anything left of Caleb the prosecutor, or are you fully committed to gunning for the government? When are you going to make partner, anyway? And what comes after that?
Last summer I got a call out of the blue from a lawyer in Philadelphia who I did some work for while I was in law school offering me a job. It was a total surprise. But my wife and I had always wanted to come back to Philly and so we just said yes and I joined Levin & Zeiger, LLP.
Before I joined my current firm I hadn’t given much, if any, real thought to how lawyers in private practice make a living. As a government employee, cases just keep appearing on your desk, and you get paid at the end of the month. The only real thought I put into the mechanics was bitching about how I wasn’t getting paid enough.
Getting butts in the door is, by far, the biggest challenge of private practice. You can be the absolute best lawyer on earth and fail miserably if you can’t convince people to hire you (and then insist that they actually pay you).
I am fortunate in that the partners at my firm hired me because they have too much work to do entirely on their own, but also want nothing more than for me to develop my own practice and get my own clients. It is a very collaborative and mutually beneficial arrangement.
One of the great things about my current practice is that I get to focus on what I want to do, versus what shows up on my desk. I still have a number of appellate cases, but I focus a lot on plaintiffs’-side civil rights cases. Those cases are a return to what got me into the law in the first place.
I wanted to be a prosecutor because I wanted to help people who were victims of crime. In practice, prosecution focuses on what the defendant did, because often the only victim is societal order.
In civil rights cases, the whole focus is on making a victim whole and righting whatever wrong happened to them. This is uniquely satisfying; particularly when my clients are marginalized members of the community who have never really had anyone stick up for them before.