‘Happiest Man on Earth’ makes Christmas magic helping Windermere community

Billy Flanigan’s business, Santa’s Old Fashioned Christmas Trees, donates to school choir, families in need

WINDERMERE, Fla.The “Happiest Man on Earth” is looking to make a little bit of Christmas magic while also giving back to the community.

Billy Flanigan has been in the magic making business for 40 years as a performer at Walt Disney World. When the opportunity came up for him to partner with a friend to open two Christmas tree lots in Windermere, it became another chance for Flanigan to spread joy to others.

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“He knew a lot about trees, I knew a lot about show business because I work at Disney World, and you know I thought what a fun way to be able to create some magic,” Flanigan said.

The lot brings smiles to people’s faces for more than one reason. Proceeds from Santa’s Old Fashioned Christmas Trees go to the Windermere High School chorus.

He said they’ve been able to raise $50,000 for the group over the last five years.

Billy Flanigan, a performer at Walt Disney World, is making magic in other ways by selling Christmas trees. (Copyright 2022 by WKMG ClickOrlando - All rights reserved.)

“We’re hoping this year we can give them a nice check,” Flanigan said. “Usually, it’s between $5,000 and $10,000.”

Windermere High School Choral Director Erin Scully Kolodinsky said the donations from Flanigan have drastically impacted their program.

“Without those funds, we wouldn’t be able to do everything we do, getting us to all of our events every year, helping pay for music, the accompanist,” Scully Kolodinsky said. “We’re just so grateful for everything Billy has done for us.”

But the giving doesn’t stop there. Flanigan plans to donate the unsold trees to families who can’t get a Christmas tree this holiday season.

“We’d love to be able to nominate some families and have them come get a tree or we’d bring a tree to them,” Flanigan said.

If you’d like to nominate a family in need for a Christmas tree this year, head on over to Flanigan’s TikTok (@TheBillyFlanigan) and comment on the video talking about the giveaway.

Flanigan will choose from nominations received no later than Dec. 12.

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About the Author

Emily joined WKMG-TV in November 2022, returning home to Central Florida.

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