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Award-winning songwriter, photographer faced homelessness until Nashville music community poured in support

It sounds like the stuff of a sad country music song, only it isn’t a song. It’s real life, though it does involve a country music songwriter, Greenport’s own (for not much longer) Hugh Prestwood.

The acclaimed Mr. Prestwood, 79, is a Nashville Songwriters Hall of Famer. His wife, Judy Ahrens, 68, is a former award-winning photographer for The Suffolk Times. Together they have been prominent North Fork icons for nearly four decades, known for the excellence they produced in their respective crafts.

So, it came as a stunner to learn recently that the retired couple was on the verge of homelessness. Facing dire financial straits, in large part because of changes in the music industry’s business model, they can no longer afford to live on the North Fork. Desperate for funds to cover costs for a move to Texas, Mr. Prestwood last month launched a GoFundMe campaign in which he outlined his plight. The page, titled “Elderly and Drifting Towards Homelessness,” went viral. Donations poured in, including those from artists, songwriters and producers of the Nashville music community and beyond. As of Wednesday, $110,290 was raised through 753 donations. The goal was $25,000.

That was a huge bright spot.

“People really helped me out here,” Mr. Prestwood told The Suffolk Times in a 46-minute interview. He said he was “absolutely shocked” by the response.

Mr. Prestwood, a Texas native, moved to Greenport in 1983 and bought a large Victorian house on First Street that was priced right, but needed a great deal of work. “We only paid out about a hundred thousand dollars for this house,” he said, “but I always said, ‘We bought a million-dollar house and then we had to put in the other $900,000.’ ”

He said, “We figured we’d die here.”

That house, and royalties Mr. Prestwood was earning from his songs, were his retirement nest egg. Then things changed. The recording industry’s business model changed with the digitalization of recorded music and the collapse of CD sales. The royalties that accounted for most of Mr. Prestwood’s income dried up.

“Suddenly, everybody was doing illegal downloading,” he said. “Around 2005, all of a sudden, my royalties just sort of stopped, and it was like, ‘Whoa!’ It was a shock.”

He said: “You can’t compete with free. No one realized that all of a sudden music was gonna be basically free.”

Hugh Prestwood, pictured in 2016. (Credit: Krysten Massa/file)

“What happened was when the royalties started to disappear, all of a sudden we had trouble paying bills and we had to refinance a couple of times,” he continued. “It just got worse and worse and I kept thinking, ‘Somehow things are going to change,’ but they didn’t.”

After living in the First Street house for nearly 30 years, Mr. Prestwood had to sell that home. Ten years ago the couple rented a house on Tasker Lane, where they currently live. Their monthly rent of $2,300 amounts to two-thirds of their combined Social Security payments, said Mr. Prestwood.

In the struggle to try to make ends meet, Mr. Prestwood sold copyrights to songs and other items. “It was terrible,” he said. “Seriously, having a flat tire was a crisis because we just had no money. We got by a little bit by borrowing a little money from friends or family and selling things. I sold quite a bit of my studio recording equipment and sold a few paintings. We just kind of scraped along. It was a struggle every month.”

Their landlady now wants to rent the house on a seasonal basis because she can bring in more money that way. That has priced Mr. Prestwood out. He said he has a March 31 deadline to move, and he can’t find affordable housing on the North Fork.

“For the last two or three years we often referred to it as if we were in a boat drifting toward Niagara Falls and we didn’t see anything around it,” he continued. “It seemed like we were doomed. We would eventually go over the falls.”

Making matters worse, Mr. Prestwood suffered a serious injury in April 2021. He said he had climbed up a small ladder to put food into a bird feeder when the ladder collapsed. He took a big fall on his back, crushing one of his vertebrae.

“I’m pretty close to an invalid here,” he said. “I can’t do much. I can walk around a short distance, but I’m in pain a lot of the time.”

The story about Mr. Prestwood’s difficulties has been reported in Rolling Stone and Billboard.

“But even if this specific campaign has a seemingly happy ending, it masks a much darker reality,” Rolling Stone wrote. “For every Hugh Prestwood, there are dozens and dozens of aging songwriters without the reputation, the network or even the know-how to get their story in front of a supportive community … Or they’re simply too ashamed or alienated to ask for help in the first place.”

An album of 15 of Mr. Prestwood’s songs, written over the course of the past 30 years, was released Aug. 14, 2020.

Mr. Prestwood has written for Randy Travis, James Taylor, Judy Collins, Jimmy Buffett and Tanya Tucker, among others. He won numerous honors and awards, including a BMI Country Song of the Year for “Hard Rock Bottom of Your Heart” and a Nashville Songwriters Association Song of the Year Award for “The Song Remembers When.” His first No. 1 country hit, “The Sound of Goodbye,” recorded by Crystal Gayle in 1983, was nominated for a Grammy Award.

“I think I became the poster child for the plight of songwriters,” said Mr. Prestwood.

Asked if he was angry at the industry, he replied: “No, no, no, not at all. I feel like I was extremely blessed, you know what I mean? God. I got inducted into the Hall of Fame and I’m just as thrilled as could be … My heydays are before everything started to go to hell.”

Mr. Prestwood, who is from El Paso, Texas, said he plans to move to the Fort Worth area, where he has two children and four grandchildren, and a lower cost of living awaits him.

Several days after the interview, a question was posed to Mr. Prestwood: Does he see himself writing songs any more?

His reply via email: “I love writing songs and doubt I’ll ever stop, but my writing has been on hold for the last year due to the crisis we found ourselves in — unexpectedly having to move and without the money to do so. Once settled in Texas I’m sure I’ll start writing again. Better yet, we’ll be able to see a great deal more of my side of our family … The only other plan I have is to eat loads of authentic Tex-Mex Mexican food.”