When I first met Dillard Morrison, Jr., all I could tell was that he had a story he could barely contain himself from telling. In a side room of a speakeasy in Harlem one night, the spry 70 year-old’s eyes twinkled as he spoke of smoky clubs and jazz, a time when nattily-dressed gangsters roamed Manhattan’s upper reaches and enforced a code of honor. Perhaps no man was more feared, respected and admired in his day than Morrison’s father, “Red” Dillard Morrison, Sr.
Once called the “most dangerous man in the country” by federal law enforcement agents, the elder Morrison’s underworld résumé includes running a multimillion dollar heroin ring and engaging in shootouts with famous rivals like Bumpy Johnson. But the part that fascinated me most about Morrison's life, as told by his son, wasn’t the gunplay or fast money. It was his abiding love for music.
Many people have heard stories of connections between celebrities and organized crime, from Frank Sinatra’s relationship with the Genovese crime family to Young Jeezy’s ties to the BMF syndicate in Atlanta, while artists from Scarface to Jay-Z often glorify the life of the mafioso. Morrison was one of the earliest bridges between the two worlds, spending countless nights at the Savoy Ballroom or Minton’s Playhouse with the likes of Count Basie and Sarah Vaughan-- and bankrolling and otherwise supporting an array of musicians, even in the midst of a flourishing criminal life.
“He was very kind to all the musicians,” says jazz singer Ernie Andrews. “He followed them all the time, gave them support.” Adds Morrison's son: “There was nobody he didn’t know. They all partied together and drank together, just like Sinatra and Tony Bennett used to do at the Copacabana.”
Dillard Morrison, Sr. was born in Alabama and migrated to New York with his parents as a teen. After deciding menial labor wasn’t for him, Morrison quickly earned his underworld stripes by robbing craps players and numbers runners in Harlem, growing into a bona fide gangster in the late 1930s. His early criminal enterprises showed no shortage of ambition: disappointed with the take of one heist at Woolworth’s, he immediately robbed a check-cashing shop. He picked up his nickname when he accidentally turned his hair red while trying to straighten it.
Even more than his appetite for illegal activity, it was Morrison’s toughness that would become the stuff of legend. In one case, he was ambushed by a pair of assailants who shot him in the leg--but he turned around and chased the gunmen all the way back to their getaway car. Though he would spend decades behind bars over the course of his life, however, Morrison was never convicted of murder.
“As far as his record is concerned, you’d say this guy is a dirty guy,” admits Morrison, Jr. “But when you’re in the street, you need to get respect. It’s like taming wild horses. When he was around the thugs, he couldn’t show weakness.”
When he wasn’t plotting with underworld operatives, Morrison spent his time with musicians and family, with the line between the two blurring over the years. In 1938 he proposed to his girlfriend, Kathleen, at the Savoy, dropping to one knee amidst a troupe of dancers whirling around before the big band. Shortly after their marriage, Morrison tried to go straight.
After the couple’s first child died at birth, however, Morrison became convinced he needed more money to get the best possible medical care and prevent another tragedy. When he was asked to become the right hand man for a boss named Big Joe, he agreed. A healthy Dillard Morrison, Jr. was born in 1941.
The younger Morrison remembers growing up with music and musicians. His father had become an advocate for the jazz players on the Harlem scene: Artists knew that if a nightclub owner tried to stiff them, they could always call Red Dillard to apply some pressure. Over the course of time, this helped to foster a number of close friendships.
“Count Basie used to come by the house,” recalls Morrison, Jr. “Anybody that you’d put him around, they’d stick to him. He’d protect you, and he’d give you advice.”
In the mid-1940s, Morrison split with Big Joe and began buying heroin wholesale from Italian mobster Lucky Luciano, who imported the stuff from Turkey via Sicily. Morrison then handed off the product to drug runners who’d resell it in points further south and west of New York. Morrison also worked as a pimp and earned a reputation as both a dashing ladies’ man and a philanderer.
As Morrison’s business grew, so too did his profile. His name began to turn up in local newspapers, both for the opulent parties he threw--and for his criminal activities. In 1950, the law finally caught up with him: Morrison was busted by the Feds on narcotics charges and sentenced to five years in prison. While Morrison was away, his musician friends visited him at the penitentiary in Leavenworth, Ks. and kept an eye on his family. Harry “Sweets” Edison even offered music lessons.
“That was when I was 10 years old,” recalls Morrison, Jr. “Sweets told my father, ‘I want to teach to your son to play trumpet.' He said, “No, it’ll mess his mouth up.’”
Morrison, Sr. returned in 1955 with promises of going straight. When two mafiosos showed up at his house with a brand-new red Cadillac El Dorado for him--a token of gratitude for not “snitching” on them in prison, he respectfully declined. He eyed the real estate business and considered opening a dry cleaning shop. But months after his return, another event shook him from his path: the sudden death of his wife, felled at age 33 by an allergic reaction to a penicillin injection.
Though Morrison frequently cheated on his wife, he was deeply affected by her death. Trying to cope, he spent his nights at clubs like Shalimar, Birdland and other old haunts. In the late 1950s, he opened his own nightclub, “Red’s After-Hour Spot,” on 146th Street. He’d drink and chase women with Thelonius Monk and Billy Daniels; he even had an affair with Carmen McRae. One night, he taught Miles Davis how to drive stick shift.
“Miles Davis loved him to death,” recalls Morrison, Jr. “Miles bought a red Maserati and drove it in one gear all the way from 77th Street to Minton’s Playhouse so that my father could teach him how to drive it.”
During this time, the elder Morrison grew increasingly fond of cocaine, and his behavior became erratic. There were more shootouts, bar brawls, and a drug deal set up by a federal agent that landed him back in jail for ten more years. Once again, his musical friends stood by him. Billy Eckstein and Sarah Vaughan even visited and performed for him at Otisville.
Released in 1974, Morrison, Sr. moved to Los Angeles and continued his life as a drug dealer even as he approached his 60th birthday. Still, he maintained his support for musicians. Ernie Andrews remembers Morrison sending money to help pay for the funeral of Sonny Payne, a drummer who played with Harry James and Count Basie. “Red sent me $1000,” says Andrews. “He was that kind of a guy.”
Growing old isn’t easy for anyone, and it’s nearly impossible for a gangster. By 1979, Morrison was back in jail for the last time, ratted out by a girlfriend and convicted of drug charges. He died of bladder cancer in prison ten years later. By then, Morrison’s Harlem was a shell of its former self. Most of the clubs had closed, and a new ethos ruled the streets.
“Cocaine was turning to crack,” remembers Morrison, Jr. “In Harlem, guys weren’t even laughing anymore.”
Though the neighborhood is still very different from what it was in Red Dillard Morrison’s day, there have been signs of hope in recent years. Between new construction, empowerment zones and the relocation of Bill Clinton’s offices to 125th Street, it seems there’s plenty of hope for Harlem.
Morrison’s spirit lives on through word of mouth, local legend and even beverages--local entrepreneur Branson “B” Belchie recently named a smoothie after the gangster. He says he picked Morrison because of what he represents: “Class reborn ... respect and honor … a necessary resurgence.”
Morrison, Sr. leaves behind a complex legacy. To be sure, he did his share of dastardly deeds and lost decades of his life atoning for them. But there's no question that he was a fiercely supportive patron of the arts, and a member of a long-gone breed of gangsters who enforced an ancient code of morals on the streets.
"He was only violent when it was necessary," says Morrison, Jr. "He was a beautiful, likeable guy."
