William "Will" Lee Massey

It is with immeasurable sadness and shattered hearts that we share the passing of William 'Will' Lee Massey, who left this world far too soon at the incredibly young age of 41. Will died at home in Cocoa Beach, Florida of an apparent heart attack. Will was born to George William and Mary Swindle Massey on July 2, 1983. Born in Gainesville, Florida, Will boldly entered this world at a whopping 11 lbs 3 oz, outweighing a set of twins born the same day at Alachua County General Hospital, a fact he often playfully noted. In his early childhood years, Will was affectionately given the nickname 'Charlie Brown' by his maternal grandfather, Papa Joe, a name that would stay with him throughout his life.

The family moved from Gainesville to Fort Walton Beach, where Will became a big brother to Alexandra “Alex” DeShon, before eventually settling in Orlando. There, he spent his formative years attending Pershing Elementary, Conway Middle, and Boone High Schools. He proudly played alto saxophone in the Sound of the Braves band, as well as soprano saxophone in the Boone jazz band. While in the band, he rose to the roles of section leader and drill instructor and was selected to receive the coveted Louis Armstrong award, the highest level interscholastic award given to students at high schools in the United States. This award is given in recognition of "outstanding musical achievement and an incredible dedication to the program". He studied under renowned musician Ernest “Ernie” Mauro, a member of the Benny Goodman Orchestra. Building on his musical talents, Will taught himself to play acoustic and bass guitar, drums, and frequently led worship with his church praise team. Though he never considered himself a vocalist, Will possessed a remarkable bass voice, drawing inspiration from renowned artists like Avi Kaplan of Pentatonix and Tim Faust of Home Free. When his musical family gathered to sing, his deep, rich voice was always heard anchoring the lowest notes.

Will had an eclectic taste in music and loved traveling across the country to attend concerts. Some of his most memorable experiences included seeing Paul McCartney at Camping World Stadium in Orlando, Billy Joel at Madison Square Garden in New York City, and following Sister Hazel wherever he could, even persuading Alex to enter a radio station contest to sing the National Anthem at a Sister Hazel concert so they could have backstage access to meet the band and watch the concert beyond the crowd barrier. After garnering votes from anyone and everyone he knew, Will was proud to display photos of him and Alex from the concert with lead singer Ken Block.

Will's passion for athletics began at the age of five when he started playing basketball and soccer. Over time, his interests expanded to include church league softball and competitive team bowling. That enthusiasm carried over into his loyalty as a fan. He supported a variety of teams, including the Washington Redskins (now Commanders), Chicago Cubs, Orlando Magic, and, of course, the Florida Gators. His love for the Cubs was sparked in July 1991 when he received a Cubs cap from his cousin Johnny Campbell during a family reunion. Will’s undying dedication to the team paid off when he proudly witnessed the end of the infamous 108 year Curse of the Billy Goat, celebrating as his beloved Cubs won the 2016 World Series in the 10th inning of game 7.

Will only applied to his top choice, the University of Florida, his father’s alma mater and the proud home of the Florida Gators. He pursued a degree in criminology and was an active member of the Air Force ROTC, completing his studies ahead of schedule and graduating in December 2004. Every November, Will delighted in the rivalry when his beloved Gators faced off against the Florida State Seminoles, his sister’s alma mater. He celebrated each touchdown with a special dance, and the siblings enjoyed making lighthearted wagers— ending with Will joyously conducting his sister as she was forced to sing the UF Alma Mater after every Gator victory.

Will found his professional stride in human resource management as an HR Generalist, with the highlight of his career being his time at Billy Casper Golf (BCG) in Northern Virginia. There, he had the privilege of golfing with and getting to know the legendary Billy Casper himself. After enduring one too many snowy winters in Reston, VA, the Florida native was thrilled when BCG offered him the opportunity to work remotely in Central Florida. He moved to Cocoa Beach, a place he had many fond memories of visiting, as it was where his paternal grandfather had retired from the Army and his father had attended high school. Cocoa Beach had also become a place that Will utilized as a weekend gathering spot for his friends and family, regularly throwing multi-day parties open to all. They often began as “Happy birthday Will; Happy birthday America” as Will’s birthday was so close to the 4th of July. Proud of his grandfathers’ military service, Will was incredibly patriotic, honoring and supporting veterans through organizations like the Wounded Warrior Project.

It was in Cocoa Beach that Will fully embraced the beach life, becoming the barefoot, tattooed, sun-kissed guy we all knew and loved. As a true empath, Will felt every feeling deeply and cared for others, sharing his generous spirit through every thoughtful gift and action.

Will is lovingly remembered and will be greatly missed by his parents, George and Mary of Tallahassee, FL, and his sister, Alexandra “Alex”, also of Tallahassee. He will forever be in the hearts of his aunts, Debby (Randy) Collins of Camden, AL, and Janey Frost of Pensacola, FL, as well as his many cousins. Will was honored to be a Godfather to Ellie Rae Baloun of Apopka, FL, a role he cherished deeply. He will be profoundly missed by countless dear friends, whom he considered family.

A memorial service for Will is planned for Saturday, March 29, 2025 at 2 pm at the Carey Hand Colonial Funeral Home in Orlando, Florida (2811 Curry Ford Rd, Orlando, FL 32806). The family will receive visitors prior to the service at 1 pm and will gather with friends and family following the service at Johnny’s Fillin’ Station (2631 S Ferncreek Ave, Orlando, FL 32806).

In lieu of flowers, donations may be made in memory of Will to the Ronald McDonald House Charities of North Central Florida in Gainesville where the family stayed while he was hospitalized for a major surgery at the age of four. (https://secure.qgiv.com/for/rmhconcf). Donors may indicate at the above link that acknowledgements be sent to the family at 2126 Fielding Way, Tallahassee, FL 32311.

“And the thought that makes me smile now, even as the tears fall down is that the only scars in Heaven are on the hands that hold you now.”

Scars in Heaven, Casting Crowns