Wings of Legacy

Celebrating the Contributions of Robert “Bob” George to Above the Clouds
While Honoring the Life of Captain David Willey

Supporting Above the Clouds
Sunday, October 18, 2026 
4 to 8PM

Granite Links Golf Club
100 Quarry Hills Drive ~ Quincy MA 02169

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About Above the Clouds & the Wings of Legacy Event

Join us for Wings of Legacy, a special evening honoring the life and legacy of Captain David Willey—beloved pilot, mentor, and friend—while supporting Above the Clouds, a nonprofit that brings joy and hope to children facing adversity through the wonder of flight.

The night will include great food, silent auction and a special appearance by one of one the amazing and inspiring children from Above the Clouds’ Dream Flyers program.

Above the Clouds is a nonprofit organization based at Norwood Memorial Airport that brings joy, hope, and inspiration to children and teens facing adversity through the power of flight. Our signature program, Dream Flyers, pairs youth with volunteer pilots for transformative flight experiences that build confidence, lift spirits, and open minds to new possibilities. We serve children ages 8 to 18 who are coping with illness, disability, the loss of a loved one, or other significant life challenges. Each child receives not just a flight, but a day filled with joy, encouragement, and connection—at no cost to their families.

The Wings of Legacy event was created to honor the life and legacy of Captain David Willey, an extraordinary pilot, humanitarian, and mentor who left a lasting impact on everyone he met. Born in Michigan and raised in the skies, Captain Willey earned his pilot’s license at 15 and went on to fly in war zones, deliver famine relief, fight wildfires, transport cargo across Asia, and eventually return home to Martha’s Vineyard where he flew commuter routes for Cape Air. Despite the prestige of flying 747s and navigating the globe, what David cherished most was the chance to return home each night to his family and to connect personally with the passengers, coworkers, and aspiring aviators he encountered along the way.

One of those aspiring aviators was Matthew Sheehan, now a pilot for American Airlines and a member of Above the Clouds’ board of directors. As a teenager working ground crew at Cape Air, Matt met Captain Willey at a time when he had no father figure in his life. David took him under his wing—sharing stories, encouragement, and guidance that would inspire Matt to pursue his own career in aviation. David became the mentor Matt never had, and his example continues to shape the way Matt gives back today.

After David’s untimely passing in a tragic 2008 crash near Martha’s Vineyard, Matt—alongside David’s family—launched this annual fundraiser to honor the man who helped him soar. Today, Wings of Legacy is more than a memorial; it’s a celebration of the spirit of mentorship, flight, and generosity that defined David’s life. Proceeds from the event support Above the Clouds and the next generation of youth who, like Matt once did, just need someone to believe in them.

Title Pilot – $20,000

• Exclusive Naming Rights
• Opportunity to Say a Few Words at the Event
• Top logo placement event signage, in slideshow, email communications, printed collateral, and website
• Two dedicated social media posts
• Verbal Recognition During Program
• Branded Item at Guest Tables (Sponsor Provided)
• Includes (16 seats)

Chief Pilot – $10,000

• Logo placement event signage, in slideshow, email communications, and website
• One dedicated social media posts
• Verbal Recognition During Program
• Branded Item at Guest Tables (Sponsor Provided)
• Includes (12 seats)

Captain – $5,000

• Logo featured on Event Signage & Website
• Logo placement in slideshow, email communications, and website
• One dedicated social media posts
• Includes 1 table (8 seats)

First Officer – $2,500

• Logo featured in slideshow, website, and email communications
• One dedicated social media post
• Includes 4 Seats

Navigator – $1,000

• Logo featured in slideshow, website, and email communications
• Includes 2 Seats

Flight Crew – $500

• Logo featured in slideshow and website
• Mention in event email communications
• Includes 2 event tickets

Ground Crew – $250

• Logo featured in slideshow and on website 
• Mention in event email communications
• Includes 1 event ticket

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