My Journey from Juvenile Delinquent to Doctor of Jurisprudence

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Following is an excerpt from Brian D. Caplan’s book, J.D. to J.D.: My Journey from Juvenile Delinquent to Doctor of Jurisprudence. Caplan’s memoir follows him from a life as a reckless juvenile delinquent (first arrested at the age of 12) to his career as a respected litigator representing some of the the entertainment industry’s bigger names. In this excerpt, Caplan recalls one of his earliest cases out of law school, and the obstacles he and his client faced to see justice done. 

J.D. to J.D. by Brian CaplanThe year was 1986, I had been out of law school for a year and a half and was still an unseasoned attorney. Peter Parcher, the head partner in my small seven-person law firm, called me into his office. I was being assigned to the case of Richard Diaz, a nineteen-year-old kid from Bayamon, Puerto Rico, who was charged with A-1 felony possession of six-and-a-half ounces of crack cocaine with intent to sell, and automatic weapons. We were to be local counsel for a celebrity mob criminal defensive lawyer from Providence, Rhode Island. Since our Rhode Island counsel was not admitted to practice law in New York, I was asked to attend the arraignment and file a notice of appearance as the “attorney of record” on the case. Little did I know that our primary counsel would only remain in the picture a few weeks, never to be heard from again.

Richard spoke no English, and I spoke no Spanish. Through the aid of an interpreter I was able to meet with him briefly before the arraignment and learn that he claimed his innocence. Richard was a fence mender in Bayamon, visiting his cousin in New York on a seven-day vacation paid for by his mother. He had never left Puerto Rico before. The criminal court complaint indicated that Richard was charged with drug and weapons possession.

Based upon the severity of the criminal charges, Richard’s lack of community contacts and his “risk” of flight, his bail was set at $100,000, a sum that a nineteen-year-old non drug dealer cannot raise. Richard was ordered to be held at Rikers Island, a high-security facility not for the faint of heart. Rikers Island is one of the world’s largest correctional institutions housing over 11,000 inmates and often ranked within the ten worst prisons in the United States.

My last communication with Rhode Island counsel was a short conversation where I was given the phone number for Richard’s grandmother and asked to get a complete factual debriefing from Richard.

Nobody told me that I could have submitted certain paperwork to the court to have Richard brought from Rikers to the courthouse. Accordingly, for my first full-length meeting with Richard, I arranged to go directly to Rikers. An interpreter was set to meet me there. At Rikers, I was ushered through numerous layers of security until I was told that Richard had not been retrieved from his cell despite the paperwork calling for his retrieval. As it turned out, there were four R. Diaz’s within the facility and the authorities had not narrowed down which one was Richard. I was told that to expedite matters I could walk cell to cell in one of the cell blocks to see if I could find Richard, and I agreed to do so. Dressed in a two-piece suit and carrying a briefcase, I didn’t quite fit in with my environs. The walk was unremarkable as I bellowed out “Richard Diaz” repeatedly until I came to a cell with a tattoo-covered muscle-bound man wearing a wife beater t-shirt who was profusely bleeding from a significant gash on his forehead. As the blood streamed down both sides of his face he attempted to wipe the moisture from his eyes. He was leaning on the bars of the cell door peering out when I walked by. This inmate was a scary sight. Our eyes connected for a brief moment, but it was long enough to set him off like a firecracker.

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“What the f— are you looking at?” he said, his voice full of menace.

As I jumped back, startled, a new air of confidence inspired this imprisoned man.

“You f—in’ think I look bad, motherf—ker? You should see the three guys that were messin’ with me.”

Enough said, I swiftly moved from my encounter down the cell block. With no luck finding Richard, I went back to the administrative offices from which I had come and was told that my client had been located. I breathed a sigh of relief as I did not want to play another round of truth or consequences walking through the cell blocks.

Richard was five foot three, frail, and unshaven. He soldered fences on farms in southern Puerto Rico to prevent cows from wandering. He was not old enough to drink in New York. On his seven-day vacation to New York, Richard was to stay with his twenty-two-year-old cousin, Elivio, who lived in a tough neighborhood on 157th Street. During their second day together, Richard and Elivio had gone to Kentucky Fried Chicken and brought back food to Elivio’s apartment. Each of the four bedrooms in the apartment had padlocks on their respective doors and there was a communal kitchen, bathroom, and living room, with a couch and television for all to use. Elivio’s was the first bedroom off the front door to the left. According to Richard, Elivio left the apartment after they had come home, his bedroom door was open and Richard was watching TV and eating chicken in the communal living room, when about forty minutes later, there was a knock at the door. Richard went to the door, asked who it was, and heard Elivio’s voice say it was Arnaldo. Hearing it was Elivio’s voice, Richard naively opened the door. Three undercover police officers with guns drawn and Elivio already in handcuffs awaited on the other side. Richard was forced to the ground at gunpoint as two of the officers conducted a warrantless search of the apartment and Elivio’s bedroom adjacent to the front door, where drugs and weapons were found hidden away under a bed.

Richard was arrested and charged with an A-1 felony punishable by twenty-five years to life in prison. Elivio was arrested and initially charged with loitering with intent to sell narcotics, a class B misdemeanor. If Richard was telling the truth, he was simply at the wrong place at the wrong time, a defense that many a judge would find incredulous.

My defense strategy was simple: make a motion to suppress the evidence claiming that Richard was arrested without “probable” cause and therefore the weapons and drugs found after his liberty was unconstitutionally curtailed were fruits of the poisonous tree (i.e., the illegal arrest) and inadmissible as evidence against him. Since Richard was visiting his cousin, under existing case precedents, he could not claim that the search of the apartment was without probable cause because Richard did not have “a reasonable expectation of privacy” in someone else’s home. If we lost our suppression motion, Richard would be in dire straits as it would be his word at trial versus the word of a number of police officers as to how he possessed the contraband.

As the case developed, I obtained through the discovery process the police’s version of the events. Elivio had been selling crack cocaine in the street when an undercover agent attempted to apprehend him. Elivio eluded his pursuer, ran into his building and made it back to his apartment with the police in “hot pursuit.” When the police knocked on the door, Elivio opened it, the police walked into the apartment to arrest Elivio and in so doing saw the drugs and weapons on a table in Elivo’s bedroom in “plain view” with Richard hovering and exercising “dominion and control” over the table.

In order to properly cross-examine the police officers, I ventured to 157th Street in Washington Heights to examine Elivio’s apartment and the scene of the arrest. I parked my Trans-Am a few blocks from the apartment, hoping it would still be there when I returned. I was wearing a blue button-down shirt but left my suit jacket and tie in the car. When I entered the building, a number of people screamed “policia, policia,” and ran in different directions. I felt like I was part of an episode of the cartoon, Speedy Gonzales, with everything and everyone moving at breakneck speed.

The lone person left in the lobby was a black gentleman calmly leaning against a wall. He took one look at me and said, “You a lawyer or you a cop?” Before I finished getting the words out of my mouth, he remarked, “You a f—ing stupid lawyer to come in here looking like that.” I asked where I could find apartment 503 and he pointed me to the stairs.

When I got to the unit on the fifth floor, I knocked and an older unshaven gentleman with a beer in his hand opened the door. He spoke little English but generally understood why I was there and allowed me in. The apartment consisted of four bedrooms, three of them locked with padlocks and an open door for the fourth bedroom belonging to my host. There was a dilapidated and torn grass green couch in front of a TV set from 1965 with rabbit ears antenna above in a living room area that apparently everyone shared, along with a kitchen and bathroom. The old man confirmed that Elivio’s bedroom, which was locked, was similar in dimensions to his little room. The odds of a drug dealer having significant amounts of crack cocaine and weapons sitting on a small table in the middle of the room, when opening the front door for the police, were slim to none.

There were a number of court appearances leading up to the day of the suppression hearing. I learned that Elivio had $347 on his person when he was arrested, and Richard had $11. The prosecutor had upped the charges on Elivio to the same offenses as Richard. Elivio had prior drug-related convictions and Richard none. Nobody could give a feasible explanation as to why the police only initially charged Elivio with loitering with intent to sell drugs if they saw him selling narcotics then chased him in “hot pursuit” culminating with his arrest in his apartment ten to fifteen feet from the drugs. It didn’t add up.

Criminal Court judges in the New York State court system have a difficult job. They generally have huge backlogs of cases and are under constant pressure to move them along to resolution. Frequently, without knowing many pertinent facts, they pressure defendants to take plea bargains. Our judge was no different. Even before the suppression hearing began, he, through an interpreter, told Richard that he should accept a plea to a Class B felony, which would carry a sentence of 5 to 25, where Richard could be released as early as three and a half years later.

As Richard continued to maintain his innocence, the judge constantly badgered him to plead guilty. On one court appearance, Richard arrived with a black eye and swollen cheek, a gift from fellow inmates at Rikers. One had tried to rape him. After three months and seventeen days on the inside, Richard’s spirit and body were faltering. It was now December, approaching Christmas, and the streets of New York were bustling with shoppers and anticipation. Richard was in a tiny cell waiting to be judged for a crime he did not commit.

The Special Narcotics Division of the New York District Attorney’s Office was under the auspices of Sterling Johnson. They were in the business of getting results and convictions, ridding the streets of drug dealers. Consistent with their hard-nosed approach, they let you know that if you proceeded with a suppression hearing in an attempt to exercise your client’s constitutional rights, making them spend the time to defend against your motion, any plea bargain offer previously put on the table would be removed. Although I had already alerted Richard to this fact, our judge drove home the point hard before the hearing was to start.

Richard started to buckle. The pressure became too much to bear. Through the interpreter, Richard sheepishly told me he wanted to plead guilty to the lesser offense, calculating how old he would be when he got out of prison. Convinced of his innocence and disillusioned by his change in resolve, I told Richard that in order to plead guilty he would need to do an allocution in open court pointing to the drugs and automatic weapons and acknowledging they were his. Richard began to cry and in Spanish said that was something he could not do.

Two police officers and Richard testified during the first day of the suppression hearing; Elivio did not. Elivio’s attorney and I each conducted thorough and compelling cross-examinations of the officers and their logic in charging Elivio initially with only loitering, which did not hold up to scrutiny. Richard was convincing even though his testimony directly contradicted that of the police officers. It was uncontroverted that Richard lived in Puerto Rico, was in New York on vacation, and that the contraband was all discovered in Elivio’s room.

Over the course of my representation of Richard, his demeanor and persona had significantly changed. Initially he was indignant and combative about his unjust arrest. Following his months of incarceration at Rikers and the browbeating from the judge, he became fatalistic and lost the will to fight for his cause. Now, at the end of our first day of hearing, Richard was seriously depressed. Fearing for Richard’s safety, I asked our judge to have him put on a suicide watch. With the stroke of a pen, his shoelaces and belt were confiscated, he was not permitted to shave, and he was checked in on a more frequent basis.

Criminal defense attorneys who have many years of experience defending accused criminal defendants learn as a defense mechanism to become detached from their clients, and not get caught up with their potential guilt or innocence. I, on the other hand, was consumed by my representation of Richard, worried that my lack of experience could facilitate an innocent man going to prison for a long time.

Before the second day of the proceeding, the judge called all attorneys into his chambers and told the two ADAs working the case that he believed Richard was innocent and Elivio was guilty, that he would prefer not to rule on the suppression motion, that the government should dismiss its case against Richard and offer a B-Felony plea to Elivio before we went any further. I couldn’t believe my ears but did not want to get too excited before anything official happened. The judge also said he would personally call Sterling Johnson and make the recommendation.

Court was temporarily adjourned. Richard and Elivio were returned to their holding cells and the ADAs were busy deciding their next moves. By early afternoon they had their marching orders. They would agree to dismiss their case against Richard subject to Elivio agreeing to the plea suggested by the judge. As soon as I heard this, I went into attack mode. How could one man’s liberty be deprived based upon another man’s decision to do time or not. Constitutional due process was being violated. If the government didn’t believe it had a case against Richard, then they should just dismiss their case against him. While the judge did not disagree, he was also pragmatic. He instructed Elivio’s lawyer to have a long talk with his client. It was 3:45 p.m. when Elivio’s attorney came back with the news that his client would accept the plea. By 4:30 p.m. we were on the record in court and Elivio was acknowledging his ownership of the drugs and weapons. His sentencing would be thirty days later.

The judge’s clerk prepared the order that I anxiously awaited, a document confirming that the case against Richard was dismissed and directing the warden to release him. The judge handed me the signed order and said, “Good job, counselor. You fought well for your client.”

My heart was racing as I carried the order to the lock-up area where Richard was located. I gave the order to an officer and was pointed to his cell. As the officer walked in, I ran. I got to the cell and said, “Tue es libre.” Richard began to cry and so did I. The weight was lifted off my chest as the cell door opened and Richard hugged me sobbing. It was the most rewarding day in court I ever had even though we weren’t paid a penny for my time.

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