15 Shootouts: Lessons From Ralph Friedman


Situation: In less than 15 years, a tough NYC cop is involved in 15 shootings, none unjustified.

Lesson: Use enough gun. Have enough guns. Be prepared to use ultimate force when you have to … and be equally prepared to cope with the aftermath.

They called him the New York City Police Department’s most highly decorated detective. He made more than 2,000 arrests. Over a period of less than 15 years he was reportedly involved in 15 shootouts, in the course of which he was forced to shoot eight criminal perpetrators, killing four. Now retired, he still carries daily, and told me, “I’m 100 percent in favor of law-abiding armed citizens. There are animals out there, and good people should be able to protect themselves.”

Think good people who go armed and find themselves in harm’s way could benefit from what this hero cop learned? We thought so too. The following quotes come from retired Detective Ralph Friedman’s autobiography, co-authored with retired NYPD Lieutenant Patrick Picciarelli, entitled Street Warrior: the True Story of the NYPD’s Most Decorated Detective and the Era That Created Him.

First Fatal

Ralph Friedman joined NYPD as a trainee in January 1968 and at age 21 became a fully sworn member of the service in February of 1970. He was assigned to the 41st Precinct in the Bronx. Most of the 77 precincts of NYPD earned nicknames from the cops who worked them, and the Four-One became famous as Fort Apache. It was one of the highest crime rate areas in the country, and young Friedman quickly began racking up an impressive series of felony arrests.

Two years on, in 1972, he had to kill a man in the line of duty for the first time. It would not be the last. He and his patrol partner, Kal Unger, had responded to a 10-31 call, burglary in progress, and were searching a dark hallway when they were suddenly ambushed by a gunman hosing bullets at them. Here is how Friedman in Street Warrior describes the terrible incident:

“Muzzle blasts lit up the area. We’d passed through a short foyer adjacent to the living room and were now standing in a hallway that led to the rear of the apartment. There was a black male three feet in front of us, shirtless, gun extended, firing rapidly. Kal went down almost immediately, firing his revolver as he pitched forward. The noise of the gunfight in a confined space was ear-shattering, and I felt as if an ice pick was being shoved into my brain. I had my gun extended and was firing rounds at the guy who was shooting at us. The room was caught up in a strobe-like miasma of light, scream and curses.

“The gunman tried to get by me, but I grabbed his shoulder and we struggled, grunting and swearing, although our voices sounded muffled given the effect the gunshots had on my hearing. Everything was happening very quickly, yet it felt like slow motion. I was fighting for my life, nearly deaf from the gunshots, and wondering if I’d been hit. The shooter was about my height, medium build. A river of adrenaline was pumping through me, and I knew if I didn’t put him down, I was gonna die. I heard the approaching cavalry — the job now a rapid response ‘shots fired,’ allowing for flashing lights and sirens all the way — or thought I did. The troops were coming, and I hoped they’d arrive in time. As we fought, I pressed my gun against the gunman’s chest, hoping I still had ammo, and fired. I heard the welcome sound of a boom, no empty chamber click. The gunman went down like a dropped anchor. I found later he’d been hit a few times, but my last round got him in the heart. The three of us had fired a total of 18 rounds in what couldn’t have been more than a 10-second gun battle inside what seems like a medium-sized closet.”

Kal Unger would survive, hit five or six times including a heart shot that clipped the pericardium. Two years on the job, it was Ralph Friedman’s second shooting and his first fatal.

Coming To Terms

As we would expect, the above incident triggered some soul-searching. Friedman would write, “There is not a cop or member of the military alive who hasn’t thought about what it would be like to take a human life. It’s something that runs through a cop’s mind often …. We were in the midst of the Vietnam War, and I’d spoken to a number of enlisted friends who’d sweated the day they would experience combat. Would they freeze? Would they prove themselves? Would they be satisfied with the way they handled whatever was thrown at them? Cops are no different; only the battlefields change. I’ve known cops and soldiers who were forever changed the day they killed. Some experience psychological problems; others drink. Flashbacks are common. Marriages are destroyed. The forward momentum of life becomes intolerable. The malady of post-traumatic stress disorder wasn’t even recognized in 1972.”

Friedman had the psychological and emotional strength to cope with it. “I viewed my actions as totally justified, and as such my conscience was clear,” he remembers. He adds, “In places like Fort Apache, day-to-day survival depends on a warrior mind-set, not only for the cops but also for the civilians. I hoped my first experience taking a human life would be my last. Realistically, I knew this to be wishful thinking and I’d be proved right … three more times.”

Enough Guns

From the beginning of his career, Ralph Friedman knew if the bullets hit the fan, he didn’t want to be the guy who ran out of ammunition. NY cops bought their own guns from a short approved list, all fixed-sight .38 Specials. Most rookies bought the required 4″ service revolver and if they could afford it, a smaller frame 2″ gun for off-duty and backup use. Friedman has explained he acquired a 4″ S&W Model 10 for duty but chose the Colt Detective Special for the latter purpose, because it held six shots, and the S&W Chief Special carried only five. Photos of his uniform duty belt show a long row of no less than 18 .38 Special rounds in belt loops. He carried backup religiously both on and off duty, and on more than one occasion would be glad he did.

Partnered with Officer Bobby DeMatas one day in the South Bronx, working in plainclothes out of an undercover taxi, Friedman saw a man pull out a handgun and shoot a teenager. Here the detective explains what happened next:

“I drove right up to the shooter, drew my gun, jumped out of the cab and yelled, ‘Police — Don’t move!’ The guy with the gun whirled and took off, but not before he and I exchanged gunfire. I was right behind him while Bobby pursued from across the street, running parallel to the shooter. Within half a block, the shooter took cover behind a parked car as pedestrians scattered … Bobby ducked behind a car directly across the street from the gunman, while I sought cover in a stairway leading to the basement of a tenement. My partner and I had the shooter triangulated.

“The gunman and I continued to trade shots. Bobby didn’t have a clear view from where he was and so far hadn’t fired at the guy, but this didn’t stop the shooter from firing at Bobby. The gunman was methodical; he’d fire a shot at each of us in turn.”

Friedman continues, “I was incredulous. How could I have missed at this range? The shooter began to reload with loose rounds (not only was this guy carrying a good weapon, but he had extra ammo — something that was rare for the times), and I took the opportunity to draw my backup gun and aim three more rounds at his torso. Still nothing. It only seemed to piss him off, because he emptied his gun at me and Bobby and began to reload again! I had to have hit him. What was keeping the son of a bitch up?

“I was behind the shooter, who was about 35 feet from me, a clear and easy shot. I aimed carefully and let two shots go. The shooter didn’t budge; instead, he fired another round at me, while Bobby, who didn’t have much visibility, fired at the shooter, striking him in the shoulder. The shooter grabbed his shoulder, dropped to his knees, and then rolled over on his back. I shouted, ‘He’s down!’ I had two rounds left and ran up to the gunman. I was a few feet away when he propped himself up and leveled his gun at me. I fired one round, getting him in the forehead, watching the back of his skull blow off. He was down for the count now, no doubt.”

Friedman would later explain, “I’d hit the gunman eight times, the last shot obviously fatal. My first seven rounds were grouped tightly, and all had hit his torso — exactly what we were trained to aim for. The results of the autopsy would show a combination of booze and drugs in his system, which I figured kept him impervious to the bullet strikes.”

This would not be the only time the backup gun saved the hero cop’s life. One day in February 1977, a sting operation involving an illegal gun sale on a South Bronx rooftop went bad, and Friedman would have to shoot two men. Things went downhill when, he relates, “… the guy with the rifle, a Hispanic man about 30 years old, walked to the edge of the roof with the weapon. He took aim at the street below and started pumping out shots. Apparently, he was showing (our confidential informant) the gun worked. What we had was something bigger than the gun sale: a crime in progress. And one that had to be stopped before the nut killed someone. It was cold, so there weren’t too many people on the street. But there were enough to litter the area with at least a dozen bodies.”

Friedman and his sergeant, Stephen Cantor, ran toward the suspects shouting “Police!” The man swung the rifle up on the cops and, said Friedman, “I fired as I ran, emptying my revolver. I hit him in the thigh and hip. He went down.”

As Sgt. Cantor secured the wounded suspect and got the rifle out of his reach, Friedman pursued the other suspect, who was fleeing. There was no time to reload so Friedman drew his backup Colt and approached a rooftop kiosk where he had last seen the fleeing felon. Then, Friedman explains, “As I rounded the corner he materialized with a raised knife, already practically atop me. In that fraction of a second I knew he had me; I was going to get stabbed … bad. I heard a shot. Cantor had appeared out of nowhere and shot the attacker from behind, who promptly went down. Sgt. Cantor had saved my life, no doubt about it.”

But it wasn’t over. Friedman continued, “The perp was on his back and didn’t appear to be conscious. As I neared him to take the knife from his hand, he quickly sprang to his feet with the blade extended in my direction in an overhand grip. I instinctively fired a round, hitting him in the stomach, killing him instantly.”

Off Duty/Retirement Guns

Looking back over his career, Ralph Friedman wrote in Street Warrior, “I considered the gun a tool and treated it with respect. I had no idea at the time proficiency with my gun would save my life on numerous occasions. I’ve been retired for more years than I was on the job and I still carry my 6-shot, snub-nosed Colt Detective Special revolver, while some other retirees opt for semiautomatics with large magazine capacities, I was good with my revolvers — I carried two while on duty — so why learn an entirely new weapon? Surviving a gunfight is about shot placement, not throwing numerous rounds at a target and hoping a few hit their mark. Training is the key, not necessarily large-capacity weapons.”

Detective Friedman’s shooting incidents weren’t all on duty. Carrying in retirement continues his habit of always being armed: over a hundred of his more than 2,000 arrests were made off duty. He got into one shootout with armed robbers when off duty.

In more than one incident, he was very glad he was carrying backup while off duty. He remembers being at a boxing match that erupted in a general free-for-all: “Once I was free of the fight and not tripping over chairs, I realized the gun I kept tucked into my waistband was missing. My backup gun, also a .38 revolver, was secure in an ankle holster. My belt holster had evidently dislodged during the melee.” Fortunately, another cop found his 4″ service weapon under a chair at the scene of the brawl.

Mark Of Cain

Many years ago police psychologist Walter Gorski defined “Mark of Cain syndrome,” the fact killing someone changes the way you are seen and treated by others. The effects run across a broad spectrum, including revenge motives kindled in those the dead criminal left behind.

Friedman at that time was single and playing the field. The time came when he was hit on by a beautiful young woman who invited him to her place after work for feast and frolic. A busy day in the precinct left him working late and unable to keep the date, and she was furious when he phoned to tell her so. Shortly thereafter, he learned how close a call he’d escaped: the woman was the half-sister of the knife-man Ralph had killed on the rooftop, and waiting in her apartment were multiple male friends of the deceased. They had planned to ambush Friedman when he arrived, torture him to death, dismember his corpse, and dispose of the pieces.

Yet a “rep” like Friedman’s can also forestall violence. Historians of the Old West have noted when Bat Masterson got a reputation for having killed 26 men in gunfights — far more than the actual count — Masterson did nothing to deny the number, because it kept many bad guys scared enough they surrendered meekly instead of shooting it out. Jelly Bryce was a legendary police gunfighter in Oklahoma and with the FBI in the second quarter of the 20th Century. His reputation was such some of his colleagues described a “Jelly Bryce Effect.” How did that work? Presume a barricaded felon. Cop: “Give up and come out. We have you surrounded.” Thug: “Go to Hell copper, you’ll never take me alive!” Cop: “Jelly Bryce is here.” Thug: “I give up! Don’t shoot!”

Something similar happened to Friedman. Ralph’s brother Stu, an officer on the Transit Authority Police that had not yet been absorbed into the NYPD, was shot and wounded in an off-duty incident. When the perpetrator learned not only were a slew of off-duty cops hunting him on their own time, but so was his victim’s gunfighter brother, he found a lawyer to tell NYPD he’d turn himself in, but only if Ralph Friedman was kept at least three miles away from where he surrendered.

The cops I’ve interviewed who’ve had to shoot multiple people in the line of duty are almost universally bitter their critics focus on these instances, and overlook the many more cases in which they could have legally shot someone, but were able to control the situation without doing so. Ralph Friedman is no exception, and writes of “the hundreds of times I chose not to shoot.” In one of Friedman’s incidents, the suspect sicced a large Doberman Pinscher on him, and as the animal lunged for his throat the cop reflexively drew and fired a single shot, dropping it with a leg wound. Once the suspect was in custody, Friedman turned him over to his partner, picked up the whimpering dog he had shot, and took the canine to an animal hospital in Manhattan.

Physical Fitness

Friedman was a lifelong weightlifter and physical fitness enthusiast. This served him well in many more hand-to-hand fights than gunfights during his police career. That career ended when, enroute to an officer-needs-assistance call, his vehicle was T-boned on his side by another responding radio car. With some 23 broken bones, he was forced to retire on disability. Doctors told him his physical conditioning and the heavy musculature that had shielded his internal organs like soft body armor, had kept him alive.


Carry enough guns. Carry enough gun. Sub-optimal 158-gr. SWC .38 Special rounds were issued during Friedman’s time on NYPD. Revolvers were superseded by 16-shot 9mm autos in the early 1990s, and the last .38 grandfathered as a primary duty gun left the streets of the Big Apple in August of 2018. Circa 1999, New York City cops at last got hollow point ammunition, and the 9mm Speer Gold Dot 124-gr. +P seems to have solved long standing complaints about feeble ammo from the rank and file of New York’s Finest.

Maximum control equals maximum hit potential. Friedman told me except for when he killed the man who shot his partner, while grappling at muzzle contact, he was able to hold his .38 in both hands in all his other shootings. He also said every shot he ever fired on the street was double action.

Have secure holsters, including off-duty scabbards that won’t dislodge from your belt in a strenuous physical fight.

Remember the more proactive the officer, the more likely he or she is to eventually and perhaps repeatedly face lethally violent resistance to arrest. Friedman’s extraordinarily high arrest record and his high number of gunfights were logically predictable, not coincidental.

Street Warrior shows Ralph Friedman to be a man of compassion, something he exhibited many times to criminals in custody, and more so to victims. Those who have had to deal with death understand the value of life. When moral people carry the power of life and death, compassion should be at least as close at hand as their holster. Friedman exemplified this ethos.

Street Warrior is a powerful read. I recommend it strongly, and not just to LE, though it would be powerful mandatory reading in any police academy. We salute Detective Ralph Friedman (retired), and thank him for his service, a service that includes making his memoirs available to the rest of us.

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