Michael O’Callaghan, a well-known Portland activist who ran for mayor last fall, died on June 18 after he was hit by a MAX train while attempting to bike across the tracks at Southeast Division and 8th Avenue. O’Callaghan was 81 years old, and by all accounts, he squeezed everything out of those years. He was a world traveler, and a dedicated advocate for a range of causes. 

“It's a loss for society to lose someone like Mike,” Jack Estes, O’Callaghan’s brother-in-law, told the Mercury. 

A memorial bike ride and ghost bike installation ceremony in O’Callaghan’s honor will take place on July 11. O’Callaghan’s family will also honor his life with a memorial potluck at Sellwood Park on July 12. 

O’Callaghan and his five siblings grew up on a farm in Tualatin. His sister, Colleen O’Callaghan, told the Mercury it was clear from a young age that her brother had an interesting way of seeing the world. 

“Even in high school, in junior high, he was a unique thinker,” Colleen said. “He traveled around the world to try and glean ideas that would benefit mankind.”

Out of those travels came O’Callaghan’s 1977 idea for a free bike checkout program in Anchorage, Alaska, where he lived for several decades. He was also well-known in Anchorage for his crusade against hunger and food waste—he was an ardent Dumpster-diver, recognizing that restaurants and grocery stores would often throw out perfectly good food. In fact, O’Callaghan found enough good food in the garbage that after feeding himself, his then-wife, and their four kids, he gave the rest to those in need. Eventually, O’Callaghan created a food network that fed dozens of people a day. He was recognized for this work in Newsweek, which gave him the title of Alaska’s “unsung hero” in 1987. 

“He fought against the man, he was an advocate for the people,” O’Callaghan’s nephew, Jake Estes, told the Mercury. “He did a lot of things and he did them selflessly.” 

After O’Callaghan returned to Portland, he took up residence in a makeshift structure near the Ross Island Bridge. During his 2024 run for mayor of Portland, he made his experience as an unhoused person and his decades of advocacy for other homeless people a central part of his campaign. 

One of O’Callaghan’s biggest accomplishments in the homeless advocacy space was his involvement in the creation of the Right 2 Dream Too housing pods—one of the first village-style housing facilities in the city, which has been in operation since 2011. A self-taught attorney, O’Callaghan advocated for people at risk of losing their homes, and fought against camping bans. 

While running for mayor, O’Callaghan promoted several initiatives he thought would help with the city’s housing and homelessness crises, including enabling occupancy of storage facilities and home garages, and charging a fee to developers with unoccupied units. In a candidate profile of O’Callaghan last fall, the Mercury called these ideas “unconventional, but plausible.” A year later, the city of Portland is now investing in a similar concept, setting aside $500,000 to initiate a home-sharing program for homeowners to rent out portions of their houses in an effort to increase the supply of affordable housing, much like a program in Atlanta that has seen success. A few city councilors have also expressed interest in the same type of vacancy tax O’Callaghan envisioned. 

“He opened up everyone’s eyes to what was going on in Portland, what was going on in the world,” Jake told the Mercury. “He had wild ideas, but he was ahead of his time with a lot of it.” 

Another notable part of O’Callaghan’s personality, which he highlighted during his run for mayor, was his dedication to biking for transportation. One of the ways he spread the word about his 2024 campaign was through sticker advertisements on bike racks, some of which are still on racks around Portland today. Biking was his primary mode of transportation for decades, and in his 70s, he embarked on a cross-country bike tour. 

“Mike rode a bike everywhere. He didn’t really believe in automobiles,” Jack Estes told the Mercury. 

Though his family knows he led a long, rich life, they still say his death came too soon. The cause of death was especially alarming, considering O’Callaghan was such an experienced bike rider who lived near those train tracks and crossed them frequently. According to reports from the scene, it seems likely that O’Callaghan felt safe to cross the train tracks after a westbound Union Pacific freight train passed, and may not have seen the Orange Line MAX train coming from the other direction. 

“I’ve looked at that train crossing a lot [over the last few weeks]. It’s scary and unsettling because he rode that same route for years,” Jake told the Mercury. “It’s natural to look for something to blame…it doesn’t seem right that someone this experienced with biking and cycling advocacy would experience this.” 

Advocates from BikeLoud PDX and Families for Safe Streets, who helped plan the July 11 ghost bike installation and memorial ride, say the event will be an opportunity to honor O’Callaghan and share transportation safety concerns. As an unhoused Portlander, O’Callaghan represented a demographic at a much higher risk of being killed while walking or biking in the city. He was the 14th person, and first person riding a bike, to die in a Portland traffic crash this year. 

Still, his family says, he should be remembered for more than the way he died. 

As his family put it, O’Callaghan was a “folk hero.” This descriptor rings true from talking to others who knew him and browsing through decades of news stories about him. O’Callaghan was a frequent subject of news stories in Alaska and Oregon, owing to his public profile and political involvement. In 1990, he sued for admission into the Alaska gubernatorial race. Asked about the experience a few years later, O’Callaghan told the Anchorage Daily News that even though he lost the race, “when you really lose is when you take it seriously because then the joke is on you.” 

Perhaps O’Callaghan didn’t take things like running for governor seriously. But he was serious about many other things, from his activist work to his relationships with his family and friends. 

“He was my really, really good friend,” his sister, Colleen, told the Mercury. O’Callaghan leaves behind four children, four grandchildren, four sisters, and several nieces and nephews, in addition to “many, many friends.”

The July 11 memorial ride will meet at 6 pm at the intersection of SE Division and 8th Avenue. More details can be found here. The July 12 memorial potluck will be held at 4 pm at Sellwood Park, Section F.