‘Do good things’: Bend man gives back after living through loss and homelessness

Published 11:44 am Monday, July 28, 2025

Once unhoused, J.R. Montgomery now volunteers, donates and urges others toward sobriety

J.R. Montgomery took a break from bagging trail mix at the Family Kitchen in downtown Bend. It was a hot day in June. 

While sitting at one of several long tables in a large, open area that serves as a dining room, storage and community meeting space, Montgomery watched a young man dressed in black who was searching for the right backpack.

Montgomery, a New York City native — from Staten Island to be exact — had donated a mound of clothes, as well as a tall gray backpack when he arrived at Family Kitchen just an hour earlier.

“When you’re living on the streets,” Montgomery said, “the most important things to have are clean underwear and socks, a dry sleeping bag, and a spacious, comfortable backpack.”

That’s hard-earned knowledge for Montgomery. Since leaving his parents’ home as a young man, he’s split his time between Oregon and the New York area. He’s lived for stints of varying durations in shelters and on the streets. Most recently, he slept in his minivan while parked in a Walmart parking lot.

At the Family Kitchen, Montgomery watched with keen interest as the young man inspected one backpack after another, tugging on the shoulder straps, plunging his hand inside to see how spacious they were. After trying a few, he finally slid the tall gray one onto his back.

The young man turned to reveal a subtle smile. His smile seemed to grow broader and brighter as he walked around the room, enjoying the feel of the backpack on his shoulders.

“That’s what it’s all about,” said Montgomery, happy that the backpack he’d donated just an hour earlier was already being put to good use. “I wake up every day. I thank God. Then, I go out into the world to try and do good things.”

But that brief, joyful moment wouldn’t last. A crisis was brewing in Montgomery’s community.

‘I feel like Job’

As Montgomery basked momentarily in the satisfaction that comes with knowing one’s help is appreciated, a tall man approached the table.

“Have you heard about our friend?” the man asked Montgomery.

“No, what happened?” Montgomery asked.

J.R. Montgomery offers some donated clothing he brought in to Scott Nelson at Family Kitchen in Bend. Montgomery said he visits garage sales and thrift stores weekly to find low cost or free items he can donate to Family Kitchen and other organizations.
(Photo by Joe Kline)

“He started drinking again.”

“Where is he?” Montgomery asked after a brief pause.

“I don’t know,” the man said. “I think he’s staying in a hotel somewheres.”

“I’ve got to find him,” Montgomery said. “I’ve got to convince him to get into rehab.”

Montgomery and that friend shared time and space in a sober living home just a few months ago. 

He’s a good man, Montgomery explained, who was always armed with an inspirational Bible verse.

“But The Bible isn’t enough,” Montgomery said, his eyes searching the room for clues to his friend’s whereabouts. “You’ve got to go to Alcoholics Anonymous meetings. You’ve got to keep busy. If any of those things are missing, and you fall down, you’re gonna go back to the drink.”

Montgomery knows that struggle, too. While he began drinking for fun as a young man in Eugene, the habit has since wreaked havoc in his life.

He turned to it when his first son died. The grief from that tragedy sent Montgomery, then a 47-year-old chef and restaurateur, on a years-long bender. He wrestled with the drink for three years before a curse revealed itself to be a blessing.

“I spent six months in county jail in New Jersey,” Montgomery said. “That was my rehab. When I was released, I had kicked the drink and I embraced Jesus as my Lord and Savior.”

That devotion to sobriety and God helped Montgomery to abstain from drink when his second son died some years later. 

Montgomery said that he feels like Job, the prophet who struggled to understand why God took away everything Job held dear. Some rabbis believe Job was a historical figure rather than a literary creation.

Like Job, Montgomery said he strives and struggles through immense despair to keep his faith. Montgomery’s first wife and his father, who loved pearl onions in a cream sauce, also preceded him in death.

He said that Psalm 37:3 — “Trust in the Lord and do good” — is his mantra.

Just do good

For Montgomery, doing good includes buying things from thrift shops and yard sales and donating them to service providers. It means offering handyman services at low rates for elderly and low-income people and nonprofits. And it means volunteering for local programs like Family Kitchen.

Family Kitchen’s executive director, Olivia Parker, approached Montgomery to say hello that day in June. The petite woman with boundless energy told FORJournalism that volunteers like Montgomery help her grassroots organization to provide an array of services to those who need them most.

“His culinary experience has been a big help in our kitchen,” Parker said. “And his donations are immediately given to the people who need them most.”

Montgomery beamed.

“We couldn’t do this without volunteers like J.R.,” added Parker.

“Olivia is my earth Angel,” Montgomery said. “She’s the kind of leader who makes you want to work that much harder.”

With that, Parker returned to the day’s long list of tasks. And Montgomery went into the kitchen to wash and store dishes.

‘I’ve got to find my friend’

Doing good also includes offering peer support for those wrestling with homelessness and substance use disorder. While research into direct peer support for the former is scarce, studies show that alcoholics who are receiving peer support are 35% less likely to relapse. 

J.R. Montgomery stands outside the housing unit where he’s stayed in one of the Central Oregon Villages locations in Bend. The Villages provide temporary shelter and case management services to those who meet criteria, including being sober. “I treat everybody like family,” Montgomery said about the other residents who live around him.
(Photo by Joe Kline)

After sleeping in his van for months, Montgomery was offered a cabin in Central Oregon Villages, which has given him more time to help others. While the cabin is only temporary, he’s on waiting lists for a few senior housing units. He’s confident that he’ll get one before too long. Until then, he’s focused on doing good.

“Since moving into the cabin, I’m donating and volunteering more,” Montgomery said. “I have more time and resources to do good. I just want to take care of my health and do good.”

But he still worries for his friends, many of whom are struggling. Montgomery said that the former are the most significant barrier to housing for many of the people he knows, but the latter can’t be ignored, because they’re often connected, one exacerbating the other.

“I’m sick to my stomach,” said Montgomery, who had made his way out into the hot, midday sun. “I’ve got to find my friend. I’ve got to convince him to get into rehab.”

With that, Montgomery said his goodbyes then made a beeline for his van. He got inside, started the engine, and sat for a moment still, staring into the sun pouring through the windshield.

Homelessness: Real Stories, Real Solutions (realstoriesrealsolutions.org) is a journalism lab funded by Central Oregon Health Council under FORJournalism (forjournalism.org), an Oregon nonprofit dedicated to supporting journalism statewide. Sign up for weekly newsletters to receive updates.