Whenever Debbie Ally-Dickerson didn’t know or couldn’t remember something, she always called her older brother. Rayman “Jim” Ally Jr. seemed to have the answers to everything.

His empathy and care for others made him a go-to for life advice and deep conversations, family and friends said. His nearly flawless memory made him a walking encyclopedia of Stephen King novels, complicated recipes and medieval history. He had a sense of direction so sharp that he could navigate the streets of Baltimore and San Francisco as well as he could hiking trails in the woods.

And he knew how to make people smile — by cracking a dry joke, letting out a boisterous laugh or flashing his own grin. His smile “lit up his face,” his sister said. “It was like sunlight.” Even when he was dying.

Ally, a native Baltimorean who spent his professional life helping people in need or experiencing homelessness, died May 12 after a two-year battle with esophageal cancer. He was 55.

He was born Aug. 6, 1969, the oldest son of a physician and a dietician. His father, who shared his name, was an immigrant from Guyana, and his mother, Phyllis, was an immigrant from Barbados.

While Phyllis was pregnant, she worked with a woman who would always talk glowingly about her boyfriend, Jim. It made such an impression that Phyllis started calling her growing baby “Jim,” too. The nickname stuck.

Ally never had an issue with making friends, and spent most days hanging out with the kids in his Catonsville neighborhood. He sometimes came home scraped up after skateboarding all day. When he was looking for a calmer activity, he tore through horror and fantasy novels.

“He was an amazing conversationalist, with deep knowledge on an endless list of topics,” said Will Scott, a childhood friend. “He was the best friend to have in the pre-internet days and you needed the real story on a subject.”

He seemed to have a sense of self from a young age, family said, and he made sure to pass on all of his coolness — especially his “edgy” music taste — to his siblings, Deborah and David.

David Ally was eight years younger than his brother, and as a teenager, often looked to him for advice. Once, when David was in high school, a girl reneged on a prom invite. Distraught, he went straight to Jim.

“I remember him not giving me a hard time, but consoling me in his way and letting me get that out of my system,” David Ally said.

Jim Ally graduated from the St. Paul’s School in 1987, and initially went off to Ohio Wesleyan University. He came back shortly afterward and finished his undergraduate education at the University of Maryland, Baltimore County, where he decided to go into social work.

“He especially had a place in his heart for kids — young people who were dealing with issues,” Debbie Ally-Dickerson said. He enjoyed providing them with guidance and support.

Jim Ally stayed in Baltimore throughout his early adulthood, especially in the Mount Vernon neighborhood. He enjoyed the city’s punk rock music scene and frequented the now-shuttered Dougherty’s Pub.

He decided to move to San Francisco near the turn of the century, drawn to California’s outdoors environment and the opportunity to help more people. He started working to support those experiencing homelessness, a rewarding job that also sometimes took a toll on him, because he cared deeply for the people he saw suffering.

His first stint in California was life-changing: Ally started experiencing burnout and decided to transition away from social work. More importantly, he had a son who died as an infant.

Losing Max was devastating, his siblings said. It forever changed the way he viewed the world, and it changed his own death plans. He scattered Max’s ashes at Ocean Beach in San Francisco’s Sunset District, and requested the same be done for himself.

Ally came back to Baltimore in 2006, but returned to Oakland four years later. He stayed in California until his father died, moving back to Baltimore in 2019 to be closer to his siblings. They had dinner together every Sunday, carrying on a family tradition their parents had started.

Food was always a source of joy and bonding for Ally. He loved trying out new recipes and sharing them with his loved ones. When his friend Kenyon Corbett first moved out to San Francisco, Ally made a huge Thanksgiving meal with an eggplant parmesan as the centerpiece.

It was delicious, even though they coated the kitchen in flour, Corbett said. It’s one of many memories they laughed about through the years.

“He smiled with his whole body, laughed with his whole body,” Corbett said.

Toward the end of 2016, Ally received a Facebook friend request from a woman he didn’t know but with whom he shared many mutual friends. Andrea Porkola-Case saw Ally’s picture pop up and scrolled through some of his posts. He looked pretty funny, and she was pretty goofy, so they started messaging.

After a few weeks, they both knew it was meant to be. Porkola-Case didn’t believe him when he first said he would fly out to her home in North Carolina to visit, but he showed up a few weeks later. They spent the next few years in a long-distance relationship, regularly exploring each other’s cities. Among her favorite memories was their trip to Muir Woods just north of San Francisco, which they both thought was “magical.”

When Ally moved back to Baltimore, they saw each other more often, and Ally developed a loving relationship with his girlfriend’s three daughters. Porkola-Case also gave Ally his dog, Biscuit, which became his constant companion. He was a big animal lover.

In the last two months of Ally’s life, the couple moved to Dover, Pennsylvania, to fulfill their dream of living in a wooded area surrounded by nature. That is where he died, with his sister, girlfriend and dog by his side.

The relationships Ally leaves behind — human and canine alike — are a testament to his kindness and openness, family and friends said. He kept in touch with everyone.

“That’s the legacy,” David Ally said. “All the different people that he’s touched and all of the people that have these memories of him and that are going to miss him.”

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