Collage by Bradley Penner

“Derrick lived. He wasn’t just alive, he lived.”

It’s 1965, and Derrick Hayes is walking to school with his younger sister, Andrea. The two walk hand in hand through the West Side of Chicago, as they do most days, when she spots a dead squirrel on the sidewalk. She screams and bursts into tears at the sight of the dead animal. Right away, Derrick picks her up and carries her to the other side of the street so she doesn’t have to look at it anymore.

“He was always my protector,” she remembers. “He’s our brother, so we’ve seen a lot of things over the years. But we always saw his spirit. His whole life, he was [always] so sincere and genuine.”

Derrick Hayes, the beloved father, brother, Street Spirit vendor, and friend to countless people in Oakland and beyond, died on Monday, December 9 due to complications of diabetes. He was 64 years old.

Derrick was born in North Lawndale, Chicago, the second-youngest sibling in a family of four. In an interview with Street Spirit back in 2019, Derrick described North Lawndale as a high-crime neighborhood where it was difficult to avoid getting involved with gangs. But after his father died, Derrick’s mother remarried, and the family moved to Sanford, Florida. Derrick attended high school in Sanford, where he enrolled in Pop Warner and played competitive baseball, basketball, and football. Derrick and his brothers were star athletes, and traveled around Florida to play sports.

At home, their life was colorful and active. His mother was a classical pianist, and after arriving in Florida, she went to music school. His parents started a popular community choir called the Sanford Community Singers, which made them trailblazers in the community. “Us being from Chicago, the sound and how my mom played, it was like nothing that they’d ever heard down here. It was Jazzy Blues—she put her own little spin on it,” Andrea remembers. 

Derrick’s stepfather was the choir director and a tailor. He would make clothing for his family, and they would travel around the state to sing. While they were home they enjoyed what Andrea describes as real, genuine childhood: going to church and then playing games in the street or open fields in the balmy Florida heat, running home when the street lights came on.

“Everyone had to be home by the time the lights went on,” Andrea remembers. “If you weren’t, they’d come looking for you to give you a whoopin’.”

In childhood, Derrick possessed the shameless radiance that defined his character throughout his life. Andrea remembers how he would break out into dance at any moment—a talent he was known for amongst family and friends. “One time he was driving in Miami, and some song came on,” she recalls. “He got out of the car at the light and started dancing. Everyone was yelling. The kids saying, ‘You’re embarrassing me, Uncle Derrick!’ He didn’t care. He was always a lot of fun.”

After graduating high school, Derrick joined the army in 1980, where he served for three years in Fort Hood, Texas. When he finished his service he moved to California to be closer to two of his children, who were living in Hayward with their mother. Eventually Derrick found his way to Oakland where he earned his name as Hustleman, or Brother Hayes.

In his own words, Oakland is where Derrick made the transition from “a gangster” to “a cry baby.” Knowing nobody when he first arrived, he resorted to old habits and became addicted to cocaine. “That was the 90’s,” Derrick told Street Spirit in 2019. “That was what Oakland was like. I became well known for dealing and playing basketball.” He spent a brief stint in San Quentin, where he used the lessons of his youth to find community in the chapel choir.

Derrick poses with his signature ‘deuces’ out front of Roses’ Taproom in Temescal. Photo by Alastair Boone.

Back on the street and looking for a place to spend the nights, Derrick found his way to the homeless shelter at the Veterans Memorial Building on Center Street in Downtown Berkeley. At the time, shelter guests had to be out the door early in the morning. Still groggy, he formed a habit of boarding BART trains to catch some extra sleep. 

He noticed the same woman every morning on the train. He learned her name, Linda Masters, and hit it off. Soon he moved into her apartment. 

For close to two decades, the couple lived in an apartment building in Downtown Oakland. But Derrick lost the apartment in 2017 after Masters fell ill and moved to Washington to attend to her health. After she left, his landlord argued in court that her departure meant that Derrick had to sign a new lease as a single occupant. This meant a major rent increase, from about $600 to $1,300 per month—a price he could not pay. After 20 years, he was back outside. 

Derrick’s time outside was hard, but he never gave up hope that he could change his life. Despite the harsh challenges of homelessness, he got sober, remained steadfast in his faith, made countless friends in the community, and worked hard on repairing his relationships with his children and other family members. 

“He was always grateful for where God brought him from,” Andrea says. 

During these years, Derrick became ubiquitous in Oakland. He excelled at selling Street Spirit because of his tenacious love of people. He made himself a sentinel in the city, watching over the community as he sold newspapers. He was quick to warn patrons when the meter maid arrived to write tickets, and once stopped a child abduction while selling papers on Piedmont Avenue. He earned his place on the side of a Downtown building after catching the attention of Jerry Smith—the president of a commercial real estate firm that revitalizes historic buildings. 

“He had this huge smile, he was unbelievably engaging,” Smith told Street Spirit in 2019. “He just seemed like a good person.” 

Derrick’s signature sales pitch was to walk up to a crowd of people and say “only in Oakland California can [you eat a bagel] and help the homeless at the same time!” customizing the phrase to the nature of the establishment. If nobody looked up or gave him a nod, Derrick would quickly cut through the crowd’s silence, using his charm to lovingly force them into facing their passivity or prejudice. “In this crowd of 20 people,” he would say in a booming voice, “not one of you even acknowledged me.” This undoubtedly caught people’s attention, and was the beginning of many conversations about homelessness—as well as numerous long-term friendships. 

“The first time I met Derrick I ignored him,” said Adrian Cotter, who became close with Hayes after meeting him on Telegraph Avenue. “I ignored him physically but not mentally. [The next time] I saw him, I decided to stop and talk. Derrick had a certain charisma and laugh and smile that made you want to talk to him.”

Derrick speaks at the Street Spirit Fall Fundraiser just days before leaving for his family reunion in Houston, November 16, 2024. Photo by Ian Castro.

Around 2019, Adrian and his partner, Liz Pallatto, started seeing him around the neighborhood. They soon developed a friendship and the couple worked to support Derrick as he began to rebuild a life for himself. When he wanted to go home to surprise his mom for her birthday, Liz got him a ticket and drove him to the airport. She bought him cell phone after cell phone, and helped track them down when they were lost or stolen. Sometimes their relationship was frustrating, but Liz says she was inspired by Derrick’s persistent desire to change his difficult habits and improve himself.

“He would go down, and he would feel bad about coming around to ask for help. But he would do it, always, as a project toward getting somewhere better,” she says, reflecting on the nature of their friendship. “You need help, you’re a human, I will help you. But with boundaries. [We worked on building] a relationship that was mindful of the other person’s humanity.”

With support from Liz and Adrian—as well as his family members, care providers, and other friends—Derrick moved inside in 2020. He was living in a tent on Telegraph Avenue when the COVID-19 pandemic struck Oakland. His age and underlying health conditions allowed him to qualify for a room in one of the county’s Shelter-in-Place Hotels, and from there he got a permanent apartment at the Nova, a supportive housing community in North Oakland.

“He was so excited,” Liz remembers. “We went over to see his apartment for the first time, and he was saying, ‘Look at this, I have my own bathroom!’” Derrick developed a habit of talking to himself in the mirror each day to motivate himself to continue making progress. He was working on improving his health, and trying to get a Section 8 voucher so he could move home to Florida to be closer to his family.

“I think the one thing I’ll be the most sad about is that I really wanted to see what the rest of the story was going to be like,” Liz says. “Even though I can appreciate that the end of the story as he lived it was a good one.”

Derrick visiting the new Street Spirit office in March 2024. Photo by Bradley Penner.

Derrick spent his final days in Houston, Texas with his family at a big reunion for Thanksgiving. He laid hands on his brothers and prayed for them, he broke bread with his aunts and uncles, and he danced with his nieces and nephews. He had lots of long, meaningful conversations with his siblings and family members, laughing late into the evening. 

Derrick fell ill on the bus ride back to Oakland, and ended up in an El Paso ICU. “When we finally got a chance to hear his voice, he reminded us that even though his body was going through all that, his spirit was strong,” Andrea says. He reminded them by singing the words to “Walk With Me Lord,” a traditional gospel song.

“That gave us comfort regarding where Derrick was…who was holding Derrick’s hand,” Andrea says. “Derrick lived. He wasn’t just alive, he lived. He lived life on his terms, to the best of his ability.” 

Derrick is survived by his six children: Derrick A. Dames of Highland, CA, Nowell D. Hayes of Miami, FL, William A. Hayes of Valdosta, GA, Ne’Shawn Dixon of Stockton, CA, Kalishia Hayes Key of Deltona, FL, and Dineshia Woods of Miami, FL; his fourteen grandchildren, Eddie Key IV, Amez Dames Sr., Autrayzia Key, Ashanti Key, Aniyah Dames, Michael Key, Heaven Woods, Ahmani Key, Keonna Gilmore, An’Niyiah Hayes, Ari’elle Hayes, Aaliyah Collier, Kal-El Key, Amina Dixon, and Harmony Hayes; his great grandson, Amez Dames Junior; as well as his three living siblings, DeAndre Hayes of Sanford FL, Michael Hayes of Houston, TX, and Andrea Hayes of Sanford, FL.

His absence will be felt all over Oakland, where his spirit remains on any busy street corner, waiting to say hello. 

Alastair Boone is the Director of Street Spirit.