It’s Portland’s most closely guarded secret – one that’s lasted over 40 years: Who is the Valentine’s Day Phantom?

The phantom is likely hard at work this week, preparing to decorate the city’s landmarks and storefronts with red hearts printed on white paper or on large banners. It’s an anonymous love note to the city that appears every Feb. 14.

Most people interviewed around town, including those who are complicit by granting the phantom access to buildings to hang large banners, claim to have no idea. Others know someone who knows – or think they do – but haven’t asked and do not want to be told. And a few people admit to knowing someone directly involved, but closely guard their secret.

“I should be able to look at my phone and find out in two seconds,” said Greame Kennedy, communications director for the Portland Museum of Art, which allows the Phantom to hang a large banner on its building. “It’s kind of a modern miracle that it’s still a well-protected secret. Even the people who do know treasure and protect it.”

Those interviewed for this story speculated that the tradition was probably begun by one person but has since grown to include a small, covert force of Cupids.

The Valentine Bandit strikes again, this time Fort Gorges in Portland Harbor in 2017. Ben McCanna/Staff Photographer Buy this Photo

In the dark of night, the phantom’s helpers hang paper hearts, large banners and flags blazed with solitary hearts on buildings. Banners have been placed on Fort Gorges, the Observatory, the snow pile on Commercial Street and the Casco Bay Bridge.

The Portland tradition has spread to other cities over the years and has fueled two parallel mysteries: Who is the Portland phantom and how has his or her identity remained a secret for so long?

Relax, everyone. You can keep reading. We’re only going to answer the second question.

Setting out on a mission to learn the secrets of the phantom, this reporter was repeatedly confronted with opposition. Many asked whether we really wanted to uncover the truth and, if so, what greater good could come of it.

“You’re going to put a stake through the heart of Portland by unveiling this,” warned Jessica Tomlinson, the Maine College of Art’s director of its artists at work program.

Several people in the know vowed to pass a message to the phantom seeking an interview, but no one responded to arrange a meeting. The mystery emissary of love has also sometimes been called the Valentine Bandit, although phantom seems to be his or her preferred title.

The earliest reports of the phantom appeared in the Press Herald and Evening Express newspapers in the mid-1970s. A 1977 article in the Evening Express said the tradition began the year before.

A woman walks by a storefront covered in hearts on Commercial Street in 2018. Brianna Soukup/Staff Photographer Buy this Photo

That also is when a second key tradition began: Portland’s investigative reporters hit the streets of downtown and the Old Port to ask questions – sometimes getting tantalizingly close to the phantom. But, perhaps not wanting to be the spoiler, they would never come back with the evidence.

A 1977 article in the Evening Express came close, saying witnesses described a man about 22 or 24 years old with strawberry blond hair and a full beard. The reporter even tracked down a man fitting the description who happened to be named Ian Valentine, but he denied doing anything of the sort.

The effort now appears to involve a whole secret network of cupids. And the phantom’s organization has been getting more sophisticated in recent years.

Longfellow Books has recently received copies of an anonymously published book about the phantom’s activities, according to bookshop owner Ari Gersen. The book being sold for $16 is in its second or third edition, said Gersen, who said he received some tips about this year’s targets. He would not provide any additional information.

The book, which has no publishing credits or information, is full of photos, newspaper clippings and anonymous quotes, which may or may not be from the phantom.

One quote alludes to a cupid crew almost getting caught by journalists.

“We had a standoff. We wouldn’t unfurl the heart until the reporter and camera man left, but they weren’t leaving until something happened. We started pelting them with snowballs from the rooftop. They seemed annoyed, like they didn’t have all night. We did. They left.”

Longfellow Books in Portland recently received copies of this anonymously written and published book titled The Valentine Phantom: Portland, Maine. The book is in its second or third edition and is filled with photos, newspaper clippings and anonymous quotes, which may or may not be from the actual phantom. Randy Billings/Staff Writer

In 1986, the U.S. Coast Guard almost caught the bandits after their small boat was almost struck by a ferry. The Coast Guard reported that a 12-foot boat was loaded with seven people. They eluded capture after hanging the 20-heart banner on the fort.

It took about 30 years before the heart showed up out there again. But Paul Drinan, executive director of the Friends of Fort Gorges, wouldn’t say what role – if any – the Friends of Fort Gorges play in planning or facilitating the hanging.

Longtime Portland resident Jay York said he was involved in the effort in the 1980s and 1990s. A studio that he and his brother George shared on Federal Street was an early meeting place for the effort, he said.

After some loose planning, the night before Valentine’s Day typically began in area bars. After closing time, inebriated deputy phantoms would disperse into the night, spreading love through the sleepy streets of Portland.

York said he never hung the paper hearts, but he was involved with the banners. He declined to be more specific or name any names.

“I’d put my life at jeopardy if I let that information out,” York said. “I have probably been too loose-lipped.”

How does one become involved in this secret society?

“Somebody approaches you,” he said. “That’s what happened to us. We had certain skills they needed.”

City officials haven’t cracked the case. Or, if they know, they’re also not talking.

The mysterious Valentine bandit was able to get a flag on the Central Fire Station flag pole as it flaps in the wind with the official fire station banner and the American flag. Gordon Chibroski/Staff Photographer

Last year, the phantom raised a white flag with a heart atop the Central Fire Station, across from City Hall. Communications Director Jessica Grondin said she wondered how it got up there, so she asked the fire chief about it one day.

“I don’t think I got a clear answer,” Grondin said.

The deputy fire chief said the only way to access the roof is through the fire station, “unless you have a really long ladder.” But Christopher Goodall insisted that he didn’t know who placed the flag there.

“I really don’t want to know,” Goodall said. “It’s a really cool thing to help people think about how they can be kinder to those around them.”

The phantom regularly hits the police station, too, placing hearts under the wipers of police cruisers and hanging them inside the waiting room of the police station. Police Lt. Nicholas Goodman said he’s not aware of anyone confronting the phantom, or reviewing surveillance footage to break the case.

A heart flag from the Valentine’s Day Bandit flies over the Portland Observatory on Valentine’s Day. Brianna Soukup/Staff Photographer

But Goodman has his theories.

“There’s multiple suspects. I feel like the Press Herald is involved,” said Goodman, who also joked about why firefighters are likely suspects. “I’ve always suspected the firemen, because they’re not as hardworking as the police. We answer more calls for service, so we don’t have time to do it, but we think it’s a good idea.”

If the Press Herald is involved, Publisher Lisa DeSisto played coy, saying this is the first time she’s heard of news carriers being implicated in the tradition.

“It doesn’t surprise me as they are masters at sneaking up to doorsteps unnoticed in the wee hours of the morning.” she said. “I think Portland PD should dust the hearts for newsprints.”

The Maine College of Art was also implicated by multiple sources, including the police. But Annie Wadleigh, assistant director of development, offered a qualified denial.

A heart from the Valentine’s Day Bandit on the door of a home on Congress Street. Brianna Soukup/Staff Photographer

“Actually, it’s not MECA students – as far as I know,” said Wadleigh, who worked unsuccessfully to uncover the phantom about 20 years ago when she was a reporter at the defunct Casco Bay Weekly. “In the past, I really wanted to know. Now, I really don’t want to know.”

She added, “It’s a beautiful anonymous love letter to Portland and one of those things that I hope doesn’t change because it preserves the heart and soul of what Portland’s been about.”

Casey Gilbert, executive director of Portland Downtown, said her group is not involved in the effort, though it would dovetail with the nonprofit’s mission of making the downtown a safe and attractive place for residents, businesses and visitors. Nor does she know who is behind it.

Sarah Campbell, director of the Portland Public Library, which has been adorned with a giant banner in the past, said she knows some of the people involved. When asked how the phantom is able to place the banner on the building, she refused to say more.

“It’s magic,” Campbell said with a smile. “Maybe it doesn’t matter who it is.”

The Valentine’s Day bandit left his or her mark on the Portland Public Library on Congress Street on Feb. 14, 2019. Brianna Soukup/Staff Photographer Buy this Photo

Kennedy, of the art museum, said the phantom has help on the inside, but he doesn’t know who is involved. “They definitely didn’t scale the wall,” he said.

Many people actively avoid learning the truth, including Tomlinson, director of MECA’s artists at work program. She said she has friends in the know who have offered to bring her into the fold.

Patrons having lunch in 2001 at Perfetto’s Restaurant on Portland’s Exchange Street share the window with a red heart left by the Valentine phantom. John Ewing/Staff Photographer

“I run screaming from the room,” said Tomlinson, who one year encountered a friend wearing black and carrying a folder full of hearts.

Tomlinson pleaded with a reporter to drop the story. At one point, she picked up the phone, as though she was about to call the newspaper editor.

So, 43 years later, the mystery continues, and the reasons are simple. Those who know won’t say. And those who don’t know want to keep it that way.

Exposing the people behind the tradition would make the day more about the individuals, rather than the anonymous gesture to the city has a whole, according to Tomlinson.

“The Valentine’s Day bandit is the heart of Portland, and as Portland continues to grow and change, it’s always a great reminder about what we love about this city,” she said. “This is a selfless act of love for the city of Portland.”