These precious family letters were left on a flight. Against all the odds, they came home

(CNN) — It’s the stuff of travel nightmares. Taking something precious on your trip, keeping it close to hand so you don’t risk losing it in checked baggage — and then realizing you don’t have it when you get home.

For Rachel DeGolia, the nightmare of losing something on a flight came true. In September, her irreplaceable collection of family letters from the 1940s to 1970s was left on a plane as it pulled into Chicago Midway Airport.

It was, says DeGolia, “tragic.” But that tragedy turned to relief — even triumph — when, after a three-week search, one dogged airline representative reunited DeGolia with her letters.

A gift from her late mother

It was the pandemic discovery that had made Rachel DeGolia’s summer.

Her mother, Lois, had died in 1996 of cancer, leaving the family bereft.

But, she says, her family were “prolific letter writers” — and in summer 2021, her cousin found a collection of letters sent by a young Lois to her brother, Phil, who’d kept them all over the years.

The letters, dating back to 1947, recounted her life — first as a frustrated teenager in small-town Lansing, Iowa, then going to college in Chicago, and meeting the man who would become her husband.

“There were all these questions we’d have wanted to ask her, but she died within four months of her diagnosis,” says DeGolia. “This felt like a gift — a window into her young adulthood. And to lose it…” she pauses. “I felt so stupid to have not at least copied them.”

Her cousin had sent them to her in batches as he went through them in the summer, and DeGolia took them with her to her daughter’s wedding party over Labor Day weekend. The celebration had been delayed a year — the couple had canceled their 2020 wedding, got married over Zoom in June, and planned a party in Brooklyn for September 2021. DeGolia thought it would be the perfect occasion to share the letters with her brother.

In her excitement, she didn’t make copies of them before the trip. And in his excitement, her brother took the precious cargo home, making sure to keep it with him in the cabin — but then left it in the cabin when he got off his flight home to Chicago.

“He was going to scan them when he got home, so he took them on the plane, put them on the floor and they were somehow kicked under his seat,” says DeGolia.

So by the time they arrived at Chicago Midway, they were out of sight, out of mind.

“He didn’t notice they were gone for a few hours,” says DeGolia. “He didn’t even get to read them.”

Letters between siblings

What her brother had left on the plane was the file full of the letters a young Lois Anne Schafer had written to her brother, from 1947 to the 1960s.

Her brother, Phil, had gone to college at the young age of 16, and the young Lois felt stifled in Lansing — a small town on the Mississippi River in northeast Iowa, which today has a population of just 968 people.

DeGolia is keen to emphasize that Lois loved the town till the end of her life, as have her kids — “We kept the house in the family where she and our uncle grew up and spend many delightful vacations there” — but as a teenager, her mother felt differently.

“She was writing about how bored she was, and how unchallenged she was in high school,” says DeGolia.

“She was frustrated with the social life in Lansing, writing to my uncle how much she missed him. She was chomping at the bit to get out of town.”

In fact, she managed it. Her brother had found it hard to adjust going from a tiny town to college — Harvard — at such a young age, so Lois spent her last year of high school living with her aunt in Milwaukee, to ease the transition into college life.

She continued writing to her brother as she moved to Chicago, where her world changed as she started her studies in social sciences, ending up specializing in urban planning.

“It opened up all kinds of horizons for her,” says DeGolia.

“She did graduate school there, she met my father, and they got married there and stayed in Chicago.

“So she wrote [to Phil] about what she was thinking and learning, music, concerts philosophical things she knew my uncle would engage with her on.

“Although I gather he didn’t write back as often as she’d like — she was always complaining about that.”

Uncle Phil may not have been good at replying, but he was excellent at preserving their family history. A “pack rat” as DeGolia calls him, he kept every letter his sister sent him.

And as she continued to write through marriage, kids, and taking care of her aging parents, who she lived near to, he kept all her letters — providing a record of her life.

In 2021, DeGolia received that whole history of her mother’s life, and her late parents’ first meeting, when her cousin found the letters. A history that could have been erased had the letters been thrown away on the plane.

The letters get lost

It was a Southwest flight from New York to Chicago Midway that had taken DeGolia’s brother home in September after the wedding party.

After the passengers deplaned, crew found the folder during their post-flight checks, realized the letters were precious, and handed the folder over to a gate agent, where it was placed in a safe.

Southwest procedure is that at the end of their shift, gate supervisors bring anything valuable straight to the airline’s Baggage Sorting Office at the airport in question — which is how the letters ended up in Sarah Haffner’s hands.

In reality, they shouldn’t have. Normally, the airline gives its airport agents 24 hours to locate the owners of high-value items — before sending them to the main Southwest lost baggage warehouse in Dallas.

In fact, Haffner — a Baggage Service Office supervisor for Southwest at Midway — had been off work for a week when the folder was brought to her office, but her coworkers hadn’t wanted to send the letters to the depot, because they seemed so very precious.

“I came back and they were on the top shelf of our high value safe,” says Haffner.

“I looked at them, but it had one of my manager’s names on it, with a note saying to hold on to it. So I left it there, thinking they knew who the owners were.”

In fact, the other staff had given up on finding the owner, having drawn successive blanks, and not having had anyone contact them direct about the letters.

DeGolia said her brother had been leaving messages with Southwest centrally — but somehow the messages had never reached the right people.

A week after her return — two weeks after the letters were lost — Haffner’s manager told her that they were at a loss.

“They said, ‘We’ve had no luck, so if you want to take a peek, do — if not we’ll have to send it to Lost and Found,” she says.

“That’s a huge warehouse of lost items in Dallas. It’s very well organized, as well as we can do it, but it’s huge. I didn’t want to send it there once I’d looked inside the envelope.”

A love story ‘like a movie’

Because as soon as she looked, Haffner had realized this was an item that needed to find its owner.

“There were about 40 handwritten letters, really aged and brown, dating from the 1940s, between family members,” she says.

“I pulled out one and read the whole letter. I realized these were people who were probably no longer here. It was stuff about relationships and family drama — it was very personal.”

In fact, it was so personal that she stopped reading. “I only read the top letter because I felt like I was impeding their privacy,” she says. “It was super private. I was trying not to read it.”

So private, in fact, that Haffner even refused to discuss the contents with CNN until Rachel DeGolia had agreed to share its contents.

The letter that Haffner had read, sitting on top of the pile, was one in which Lois was telling Phil about a man she’d met at graduate school, and fallen in love with.

They’d got engaged — only to find that neither family wanted the marriage to happen.

“Both sets of parents disapproved because he was Jewish and her family was Protestant, and they didn’t think it would work,” says DeGolia. “It was a great letter.”

“It was like a movie,” adds Haffner. “She was writing this letter, sibling to sibling, fighting for their love because her parents didn’t think he was the right man. She was pleading, writing that he was a great person. It was so sad. I read it, and I said, I just can’t send it to Dallas.”

The sad letter had had a happy ending. Lois Anne Schafer and Frank Rosen married in 1949. They had three kids — Rachel being the oldest — and were together until Lois died in 1996, after 47 years of marriage.

“It did work,” says DeGolia of her parents. “They had a great marriage.”

Haffner was fascinated by the letter. “I was so curious as to what the end of the story was — did they get married, live happily ever after?,” she says. “It was far too sentimental to send to the warehouse.”

Finding Rachel

Normally, the procedure for reuniting items with their owners is fairly simple. Non-valuables are shipped straight to the Dallas warehouse and entered into the inventory there, while high-value items get a 24-hour grace period at the airport at which they are found. Agents like Haffner look for any identification on the item, and then match the name to a passenger booking.

If the person has been on a connecting flight, that’s not an issue, because they have a database of passengers going back a couple of years.

There was just one problem. The only identifying name in the whole batch of letters was one Rachel DeGolia — and she hadn’t been on the flight.

Haffner and her colleagues tried their best. They combed through their passenger data but couldn’t find any record of a Rachel DeGolia — “It goes back two or three years, but with the pandemic she probably hadn’t traveled,” she says.

“We were trying to match the names in the letter with her last name, but obviously hers is a married name.”

After a week of running search after search, Haffner went off piste. She decided to abandon the Southwest database — and turned to Google.

And there she found details of a Rachel DeGolia from Ohio.

“I was like, what are the chances — it’s got to be her,” she says. She managed to track down a phone number.

“At 9 p.m. one night I got this call,” says DeGolia. “She said she was Sarah from Southwest, and I stopped her — I said, ‘Did you find the letters?’ I couldn’t believe it, it was amazing.”

Haffner, for her part, had “goosebumps.”

“This was the most precious thing I’ve ever had to locate,” she says. “When monetary stuff goes missing, people are relieved we have it — phones, laptops, purses, they’re happy you have them but they’re not sentimentally attached.

“But this was once in a lifetime. Rachel got super choked up, and I did too.” She starts tearing up as she remembers their conversation.

“The day before, I’d gone home thinking, ‘We’re not going to be able to find them, we’ll have to send them to Lost and Found,'” she says. “But it’s so huge, and I knew the chances would diminish of them being located. It was so obvious those letters meant so much to someone. I just couldn’t do it.”

A legacy found

Normally, Southwest customers must pay the shipping fee to be reunited with their lost baggage. But this time, Haffner offered to pay for a taxi to get them back to the family. DeGolia didn’t even trust that, anymore — she sent her sister-in-law straight to the airport to pick them up, although by that point Haffner had gone home.

“Rachel wrote me a letter — an old school note, mailed to Midway,” she says.

“It was so appreciative, and so funny — she said she couldn’t believe we’d found them, that they’d truly believed they were gone, and that otherwise they’d have had to kill her brother. That’s their family legacy, and I was so glad we were able to find them. Those letters were clearly meant to be passed down through the generations.”

DeGolia, in turn, calls Haffner a “wonderful young woman” for saving this “snapshot of what [my mother was like] growing up.” A long-time Southwest passenger — “We’e been flying since the airline opened, because our childhood home was 10 minutes from Midway” — she’s delighted her loyalty has been repaid.

Meanwhile, she and her family are discovering still more letters. “My family were prolific letter writers, and I have boxes that my grandmother wrote,” says DeGolia. “And I think my mother kept every letter my grandmother sent her, and she wrote her almost every day for years and years.”

Although she’s careful to add: “I can assure you they’ve been scanned, now.”