In the gentle glow of first light on July 2nd, 2021, Aspen lost a beloved character—and Aspen Mountain lost a legend. Ray’s profound life and plight against cancer was powerfully fueled by the love and laughter of friends and family, giving him strength to keep rallying against all odds. He departed surrounded by the same love and laughter, leaving us a legacy to be savored as long as stories are told.

Ray was born in wartime on December 5th, 1941, the oldest son to John and Della Smalls of Monticello, New York. Johnny promptly went off to war, returning home a decorated veteran with a purple heart. At home, Della laid the foundation for raising a family in hard and simple times. Modest beginnings instilled grit, determination, and an iron-clad work ethic which would serve Ray, his three sisters, and younger brother well. Versed and skilled in the family trade of plumbing and heating, Ray worked alongside his father and brother from a young age while the Smalls family name became deeply respected in the Sullivan County community.

However, it was not all hard work in the golden age of the Catskills; Ray enjoyed time afield, unlocking the magic of his home hills with rifle and fishing pole in hand. In his teen years, Ray would find his guiding light and passion on the slopes of Holiday Mountain’s 400 ft of vertical. Armed with overflowing natural talent on skis, 220 Head Standards, and a pioneering spirit, the big mountains of the West were calling.

Ray discovered Aspen in the winter of 1962 en route to a Canadian ski instructor certification exam in British Columbia. Ute City’s big mountains and bigger personalities resonated immediately. With a collection of extraordinary wanderers and locals alike to celebrate the spoils of the day from first tracks to last call. There was no doubt this towhead from the “sour cream Sierras” had found his Mecca. Ray loaded his silver Corvette Stingray with his ski gear and plumbing tools and trailered his dirt bike cross country, straight-lining for the Colorado Rockies. He rolled into town and called Aspen home for good.

In short order, Aspen’s best skiers were put on notice by a guy with surprisingly skinny legs, coke bottle glasses, white blond hair, and a skiing technique that married finesse and power. He gracefully solved the enigma of powder and elevated the game with effortless flow and beauty. His lore grew quickly with a persona that eclipsed his abilities on snow. His feet were lightning fast, but he was even quicker with a joke, boasting wit sharper than his edges. For many, he earned the title “best skier on the mountain,” and for all those who reveled with him sharing life in the fall line, everybody wanted to know “Whitey”.

His unique brand of charisma and uncanny ability to always sniff out a good time made him a leader among all those with the vision, and good fortune to make their pilgrimage to Aspen— when possibilities were endless and being a ski bum was the ultimate badge of honor. It was an epic era for a cast of characters who would individually and collectively spawn the energy, funk, and charm at the heart of Aspen’s greatness, setting our mountain town apart from all others. Ray challenged his closest friends and family members to join him on the ride and many of his Catskill confidants took up the charge, making the move to Aspen to be with Ray. These funloving nomads and powder seekers would ultimately settle down, raise families, and become pillars of the community they loved.

Whitey too tried to settle down, falling head over heels for a show stopper from the Midwest. Karen McCarthy, having met Ray on a ski vacation in college would promptly move to Aspen to carve alongside the man who stole her heart. They married quickly and Karen joked that she fell for the dashing ski pro without fully vetting the plumber in the summer. Their marriage was short lived, but a beautiful friendship endured, both never leaving Aspen. They had one son, Ryan, who fell right at the base of the tree. Ray artfully imparted his passions on his son, providing them both an incredibly close life on the snow, in the woods, and on the water as father and son while remaining best friends and partners in crime. Karen and Ray are now reunited in a place where the elk are always bugling, and the powder is dry and deep.

For a man with so many talents, Ray’s greatest body of work was the difference he made in the lives of others. In an opus that spanned fifty years of service to the Aspen Skiing Company, Whitey changed lives one turn at a time. His teaching style was “Jedi” in nature, almost tricking his clients into improving by keeping them entranced by a seemingly endless river of good times and laughter. Ray put people at ease and brought out the best in them, all while welding them together in his world as one family sharing the best of life, connected by skiing and forever bonded by the mountain.

Ray’s immediate family would continue to grow as well. In his fifties, he would be confronted by the wilds of his youth and one fateful Catskill night at a drive-in. A beautiful convergence of cosmic forces united him with Maddie, the grown daughter he never knew he had. A few years later— and never one to operate from a master plan— he and his girlfriend Lis welcomed Lilli into the world. Feminine energy now balanced his otherwise overtly masculine existence and served to soften an increasingly gruff and calloused exterior. He loved his girls dearly.

On closing day in April, with a body ravaged by leukemia, Whitey took to the slopes of Ajax one last time to make his final turns with his grandchildren Zala and Luka. On legs of rubber, held up by sheer will and expertise, he gritted it out to symbolically pass the torch to a younger generation of Aspenites. With the unspoken message to live and cherish a life on skis that is equally inspired and inspiring. Upon reflection in his final days, Ray summed it all up with gratitude by saying…“ I had the best of it”.

An on-mountain celebration of Ray’s life is being planned for early December. We fully expect a powder day. To honor Ray’s legacy, please consider donations in his memory to the Aspen Valley Ski and Snowboard Club to perpetually support kids who dare to dream big and temp greatness on snow. www.teamavsc.org/donate.