Former lawyer shines shoes as a way to give back

Published: Nov. 21, 2019 at 8:35 AM EST
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Sometimes lawyers are accused of during dirty work, but one lawyer is rolling up his sleeves to shine shoes for charity.

Earlier this week, a group of hotel managers thought they were just getting treated to a shoeshine, but little did they know they were actually about to receive a lesson in giving.

The man sitting at their feet and scrubbing at their toes is a successful health lawyer, representing a large majority of the hospitals in New Hampshire, including Dartmouth-Hitchcock Medical Center.

When Neil Castaldo retired from his practice in 2014, he knew he wanted to continue to do good, but in a much different way.

"Me shining their shoes as a shoeshine guy, nothing more. I was not threatening, I just wanted to talk, and I think that made people feel comfortable, whether it's a deep connection or we're talking about the weather, I connect with the people. I feel happy, surprised, sad, worried, empathetic and these feelings make me feel human," Castaldo said.

He says this unique way gives him access to different people and their stories.

"I shined her boots and I said, 'The shine's only going to last about three or four months.' And she said, 'Oh, that's perfect.' And I said, 'Why?' And she said, 'My oncologist yesterday told me he confirmed my diagnosis of pancreatic cancer and he said I have two to three months to live, so this works out great.' Moments like that don't happen in ordinary life. You need to have a connection with a person. And it's hard to connect with people you don't know," Castaldo said.

After offering shoeshines outside the Hilton Garden conference room for $3, all of the money raised will be going to the King Street Center, a Burlington nonprofit that provides early education and afterschool programs for children and families.

He then slipped away to change into a suit and make a presentation about giving to the unsuspecting audience of hotel managers.

"It's like Superman -- from Clark Kent to Superman," said Sean Riley, the president and CEO of Maine Course Hospitality Group. "He just had this intense need to serve, and it was exactly the kind of message we were trying to give to our leadership teams. They serve their associates. They serve the housekeeper, the person who's scrubbing the floor, you get down and help them."

Doreen Salls, another hotel general manager, said it was inspiring to meet him and that she may have been hesitant at first to sit on Castaldo's stand. But she says after seeing the outcome, she'll carry that courage to take a risk and talk to a stranger into her own work.

"I don't know if I can do this, I feel a little weird about it. But the minute I sat down in the chair, I felt so comfortable and I realized what a gift it was just to have those few moments speaking," said Salls.

"We need more connections like that in the world. We need to recognize that we're far more alike than different," said Castaldo.

Castaldo raised $1,000 for the King Street Center in Burlington from the Hilton event. The Maine Course Hospitality Group presented the check to the executive director following the meeting.