The Cheekwood Society Celebrates Extraordinary Philanthropy

Members of the Cheekwood Society gathered on the Swan Lawn for the 31st annual Cheekwood Society Dinner, for which event designer Amos Gott created a beautiful and subtle nod to America’s 250th birthday. Champagne and wine circulated on silver trays, in a setting where willow basket centerpieces played against rattan shades on dinner tent chandeliers. 

As guests took their seats, wine stewards arrived with glasses of Champagne — signaling exciting news to come. Cheekwood Estate & Gardens CEO Jane MacLeod shared the journey the organization had been on to renew its parking arrangement through Metro Parks and emphasized the urgent need for a parking structure by the end of 2027. 

“But here at Cheekwood, we take lessons from the trees and the flowers that bloom each year despite late freezes, ice storms, drought conditions and wind storms,” she said. “And like our gardens, if we’re anything, we are resilient.”

Then, with a dramatic pause, Jane asked everyone to raise their glasses as she announced that donors had already quietly made  more than 1,000 gifts in support of a new parking pavilion, totaling $22 million toward Cheekwood’s goal of $26 million. The room erupted in applause.

After dinner, it was time for annual awards, with three honors going to stalwart supporters of Cheekwood. The Jane and Guilford Dudley Award for Excellence in Philanthropy went to Neil Krugman. The Cheekwood Corporate Award for Excellence in Philanthropy went to Genesco. And the James A. Webb III Award for Extraordinary Service to Cheekwood went to Deby Pitts, a passionate gardener and the outgoing president of the Horticultural Society of Middle Tennessee. 

“I see Cheekwood not only as a historic estate, but as a place that nourishes my soul with its beauty and its pure nature,” Deby shared. “As I watched my children — and today, watch my grandchildren — explore the mansion and the gardens and enjoy the magic of Cheekwood, it makes me understand that the reason that we’re all here tonight is that we are creating the future for the next generation.”