An excerpt from “Stories of Pensacola’s Finest,” available on Amazon
By Mike Simmons
Jerry grew up in north Santa Rosa County, enjoying the rural lifestyle. So, what do boys in the rural South do in the 1950s? Boys played sports, helped the family on the farm, and enjoyed the freedoms of a relatively safe community. When Jerry was thirteen, he moved from Allentown to nearby Jay, Florida. He hunted in the Escambia River swamps daily. He became quite proficient with guns, owning both a shotgun and a .22 rifle. He developed his shooting skills with both guns. Little did he know that he was preparing for his future. When he entered the seventh grade, a life-changing experience occurred. At the school water-fountain he met a girl named Julia. They began the courtship like all adolescents do, like writing notes to each other. Jerry’s mother took them “on a date” to a boy scout party! They were typical kids. This relationship lasted throughout junior high and high school. In high school, their friends joked that they couldn’t say “Jerry” without saying “Julia” also!
It was during this time that Jerry developed his love of red lights and first dreamed of law enforcement. He worked at a local service station and, at fourteen years old, drove a wrecker! He loved the speed and was enthralled with the traffic lights and what they represented! The only law enforcement people he knew were highway patrolmen, so he decided he wanted to be one of them!
Life continued in its carefree style for the 17-year-old boy. He was the center on the high school football team. Every moment his job allowed, Jerry was in the woods hunting. His hunting skills improved daily. He provided food that his mother proudly cooked. He and Julia went out every Friday and Saturday, and to church on Sunday. Life was good!
It had been going on since 1954. Everyone was aware of it – it had been in all the newspapers. Every day it looked more and more like our country was going to be dragged into it. It was the conflict going on in Vietnam. As the time for graduation from high school came for Jerry and his friends in 1960, the buzz among the male graduates was to “join up.”
Jerry did just that. He enlisted just like his father. After basic training, he wanted more. Then he heard that the paratroopers were accepting new soldiers. He would like that, and…he needed the extra money. So, he applied and became a paratrooper, a job he held until his discharge.
But, while Jerry loved the excitement that his job brought, he and Julia were miserable apart. In the five years that they had been dating, they had never been separated. So…against parental wishes, they decided to marry. In March 1963, Julia boarded a bus in nearby Flomaton, Alabama, bound for Fort Campbell, Kentucky. Henry was waiting for her when she got off! The couple immediately made the four-hour trip to Ringgold, Georgia where they married! The newlyweds made their home at Fort Campbell and lived there until Jerry’s discharge. When that happened, they packed up and drove straight back to the familiar community of Jay, Florida, surrounded by family and friends.
As soon as his discharge went through, Jerry found himself unemployed. It wasn’t a good feeling, so he went in search of a job. He could do anything with his hands, but he wanted something more. He couldn’t stand the thought of working in an office. He wanted something that was exciting and adventurous, and he wanted Julia to be proud of him. He had heard that there was a job opening at the Pensacola Police Department. That would be a good choice. It was thrilling, honorable, steady, and stable. When he told Julia, an idea struck her. Her father’s brother, Russell Hamp, was a lieutenant at the police department. Maybe he could give Jerry some direction.
So, Jerry applied for the position of police officer, and he got the job! He found that it was a great fit! He loved it. Henry Gerald Cassady found that he not only liked helping people and enforcing the law, but he was good at it. He loved coming to work and, even better, got paid for it!
The couple continued to live in Jay, Florida, where they raised two daughters and a son. Henry worked in many areas of the department but enjoyed working as a patrol officer best – a cop’s cop is what he was known as. It was in Patrol that he interacted most with common people. Henry loved being on the street and the people loved him being there. He treated people with respect. He wasn’t soft, though. He was known as fair, but tough. As a matter of fact, over his career, he fought many people, took many to jail, and even had to shoot several people – every one of them justified.
On April 3, 2021, the author interviewed Henry. When asked about the shootings, he described them. One story, however, brought a chuckle out of him. It occurred on June 1, 1969. An armed robbery of a jewelry store was reported to the Pensacola Police from Fort Walton, about fifty miles away. The suspects were last seen heading toward Pensacola. The best way to intercept them was to wait for them along the only avenue they could take to Pensacola – over the Pensacola Bay Bridge. After what seemed like hours, they spotted the car. As soon as they moved in, the car jumped the median and into oncoming traffic. The chase continued west toward the Firehouse restaurant where Officer Glenn Darling was waiting for him. The car rammed Officer Darling’s car. The two bandits were Robert “Dude” Bradley and Shirley Sapp. With the officers in chase, Dude jumped out and started running north on foot through the parking lot and over the railroad tracks. Henry took aim and shot, striking Dude in the gluteus maximus – in his hindquarters.
Henry’s assertive police work caught the attention of the police department’s command staff. When a new strike force was formed to combat violent crime in the city, Henry was chosen to be on the team. The team (later known as the Tac squad) was so successful that violent crime was cut in half within a few years. For many years afterward, the reputation that Pensacola had as being a place that out-of-town criminals didn’t want to venture was due to the actions of the strike force. Henry also worked as a narcotics agent and as a detective.
In 1980, Henry was promoted to sergeant. From this position, he could better supervise young officers on the street while still serving the public. On January 7, 1981, Sergeant Cassady had just finished lunch. It was early afternoon, and he went back to patrolling his favorite part of town – the west side. From the intersection of Reus and Wright Streets, he looked northwest and noticed smoke rising above the houses in the neighborhood. It was January and one would expect a fire in a fireplace. But this was in Florida – it was a comfortable 61 degrees. Could it have been smoke from a fireplace? Yes, but there was a lot of it. It didn’t look right, so Henry decided to investigate.
As he turned the corner onto Belmont Street, he could see the house where the smoke was coming from. No, this wasn’t from a fireplace – the house…was on fire! Good thing it was in the day and not at night when people might be caught sleeping. First, he called it in and asked for fire department response. For good measure, Henry thought, he would check the house and make sure no one was inside.
As he got closer, he could see that it was quickly filling with smoke. It wouldn’t be long before nothing would be visible inside. When he entered through the front door, he first saw what he thought was a small child. Yes, it was a small, frightened child. Just as he was about to get the child out, he noticed a second, even smaller, child. Both were scared stiff – they weren’t moving – which placed their lives in danger.
In one motion, Henry scooped both children up and got them outside. He decided that he would have to go back in and check for others. An adult male was in the house, gathering his belongings. Henry ordered him out of the house, and he complied. Sammy Tolbert (6) and Perry Tolbert (6) probably would not have survived if not for Henry’s actions. A few seconds later and the room would have been filled with smoke, overcoming the children, and suffocating them. For his actions, Henry was awarded the Pensacola Police Department’s Bronze Cross.
Four years later, Sergeant Henry Cassady wasn’t at work. As a matter of fact, Henry had been on vacation for two weeks, and he looked like it. Henry only shaved when he had to. Not only did he have two weeks of scraggly beard, but he was wearing camouflage clothing and was driving his pickup truck – didn’t look like a cop. As a matter of fact, he probably looked kind of scary!
In a police officer’s life, complete relaxation is never possible. A cop always thinks “I wonder if someone I arrested is out to get me” or “Maybe they’re stalking me now – or my family…” Most cops carry a gun with them on- and off-duty, just in case. Henry was no different, except that he still carried his trusted .22 behind the seat in his pickup truck.
Only when he had business in Pensacola did Henry venture into town. He preferred to spend his time in his hometown of Jay, where he and his family lived. But on January 15, 1985, he had to come into town. As he was driving along Davis Highway north of Pensacola, he heard a gunshot. Of course, it got his attention, but not like a lot of people. Most drivers would have been looking for a place to get out of the way, but not Henry. If the shots were meant for no good, he was determined to stop whoever was doing the shooting. He looked around and, as he heard another shot, he saw a man running across University Parkway. It looked like he was running from the Citizens and Peoples Bank.
Henry wasn’t aware, but the suspect had horrible luck. Just after robbing the bank, he had been confronted by Escambia County Sheriff’s Corporal Bob Pollock. The robber had shot at Bob, who was still in his car. Bob returned fire from inside the car, shooting his window out. Shooting through a window at a suspect on the run and striking him amounted to some fine shooting. At least one of Bob’s rounds had hit the suspect, but it didn’t stop him.
Was it bravery or foolishness – to go up against him? The easy thing to do would have been to keep on driving. After all, Henry was on vacation. No one expected him to stop, and no one would have been upset if he didn’t. The smart thing to do was go the other way, which is what most citizens do. The brave thing to do was to face the danger. And this was dangerous. It looked like a man had just robbed a bank and now someone was shooting amongst hundreds of drivers, passengers, and pedestrians!
He knew just what to do. He assessed the situation, then immediately pulled his truck into the parking lot, and parked in a tactical manner, using the pickup as cover. Then he took up a position that triangulated the three men. Henry later described himself as looking like Fidel Castro. As Henry jumped out of his truck with his off-duty pistol in his hand, Corporal Pollack looked at him – a scraggly-faced, camo-dressed character with a gun. Pollock didn’t recognize him. He must have thought “Oh, great! More trouble – this is the last thing I need!” Was this guy for him or against him? Henry ordered some bystanders out of the area and asked Bob how he was doing.
“Fine” was the answer from the wary-eyed corporal, followed by “Who are you?” Henry quickly supplied him with the needed information, “Cassady with PPD.” To Bob’s delight, he now had a comrade. The two veteran officers communicated as to the next course of action.
Bob said “I’ve got an Armed Robbery suspect. He has already taken shots, so he’ll probably do it again. Be careful.”
Henry explained that he had a clear shot.
“Take the shot!” Bob shouted, relieved. “Shoot him!”
Henry called to the suspect three times to put down his gun. No answer. Henry, out of options, carefully took aim and fired once. Nothing. The suspect didn’t fire back. Was he hit? Was he reloading? Was he dead? Was he waiting for them to creep forward and investigate?
Then the officers heard it – a groan. The suspect had been hit. He was down. The fight was no longer in him. It was over. The suspect was wounded, but not killed. Carefully, the two lawmen eased to where the suspect was crouched. He had been struck in the neck, in the arm, and in the hand. It sent a message that it wasn’t a good idea to enter a shooting duel with the dynamic duo!
At the 1986 Pensacola Police Department Awards Ceremony and Banquet, Henry Cassady was the first person to be awarded the Department’s Gold Medal of Valor for his actions at the bank robbery.
Henry went on to work at the Pensacola Police Department for thirteen more years, helping other officers, citizens, and even lawbreakers. Henry retired in 1998. Even though everyone knew him and called him by name, no one really knew what he had become until after his retirement. He became a legend.
After a few years, Henry Cassady suddenly appeared – back on the streets – in an unfamiliar uniform driving an unfamiliar police cruiser. He explained that he had been approached by the Department of Juvenile Justice to seek out wanted juvenile offenders and take them into custody.
“How can a man Cassady’s age run down fast-as-lightning juveniles?” someone might ask. Well, if they knew Henry, they wouldn’t ask. The respect people had for him and the trust they placed in him was his ally. Mothers, fathers, grandmothers, and grandfathers knew Henry from “the old days” and, as soon as they discovered that Henry was looking for their son/grandson, etc., they would secure the youngster and call Henry to come pick him up.
In speaking with the superintendent of the Juvenile custody center one day, the author asked, “Do you know Henry Cassady?”
The man laughed and said “Yes, I know Henry. EVERYONE knows Henry!” Then he added “When I arrive to work on Monday morning, I can tell you if Henry Cassady worked the weekend before because of the population of the custody center. If Henry worked the weekend before, there will be a 20% rise in the population!”
After ten years of collecting juveniles and visiting with old friends daily, Henry retired and remains so to this day.
Henry was once asked, “What makes a hero a hero?” Henry thought about it and said, “It’s assessing a situation, knowing what has to be done, and having the nerve to do it.”
That describes Henry Cassady.
