Leo E. Karl, Jr., 94

April 18, 1929 – January 13, 2024

Leo Emil Karl, Jr. of New Canaan, CT, passed away peacefully in his home at the age of 94 on January 13, 2024. A life well lived would be appropriate, but historic legend and pillar of his community says it best in every sense of the word.

A devout Catholic, son, husband, brother, father, uncle, grandfather, godfather, businessman, civic leader, and man of principle, endless wisdom, random facts, determination, modesty, selective and deliberate words, humor, and endless love has left an indelible mark on all who knew him.

Leo was born in 1929, on the eve of the Great Depression, to Leo Emil Karl and Rose Leontine Kelley Karl on his father’s birthday, April 18, and thus became his namesake. He was born in the family’s home on Carter Street and would go on to attend the one-room coal-fire heated Little Red Schoolhouse, just a block up the street, where his aunt, Miss Mary Kelley, would be his teacher during those formative years.

In the 1920’s, the Karl and Kelley families were already actively involved in many aspects of life in New Canaan. Leo’s maternal Grandfather, Henry Kelley, helped establish the Bristow Bird Sanctuary in 1924 and laid the cornerstone for the ‘new’ New Canaan High School in 1926, a building that today is being renovated for New Canaan’s Police Headquarters. Between grandparents, parents, aunts, and uncles, Leo was exposed and inspired to a life of faith and gratitude.

From the Little Red Schoolhouse, Leo matriculated to Saxe Middle School, then New Canaan High School (Class of 1947), and was in the first graduating class from Fairfield University in 1951 with a Bachelor of Business Administration degree. While he was in college, at age 22, Leo lost his Dad to illness. The loss of his father at a young age instilled an appreciation of family relationships which would become a central core of his being.

In 1952, he was drafted into the Korean War and served in the U.S. Army as a Communications Officer in the 110th Infantry Regiment in Germany until 1954. During those years in Europe, Leo developed a lifelong love of travel and adventure, covering many cities with his sister, Mary and brother, Ed. In 1957, after returning from the war and completing post-graduate studies in Merchandising and Management, Leo joined his brothers Henry (Harry) and Paul in the family business and was appointed President of the Karl Chevrolet dealership by General Motors Corporation, one of the original Northeast Chevrolet dealerships, which was started by his father in 1927.

The 1950’s were a busy time in Leo’s life, as he met the love of his life, Katherine Margaret Horan (Kathie), an elementary school teacher from Fairfield. As a wedding gift, Leo was granted two and a half acres of woodland and wetlands at the back of the family farm on Silvermine Road. After walking the land and seeing the potential of a grove of maple trees and stand of hemlocks, he set out to clear a building lot by hand with the help of family and friends. Within a year he laid the foundation and built a small home where he would raise a family of ten children and initiate his legacy.

When recently asked by one of her granddaughters if she’d ever won anything, Kathie quickly replied, “Yes! Grandpa’s heart. The BIGGEST prize ever!” Leo lived a wonderful life focused on his three core pillars: Faith, Family, and Community.

He was a lifelong member of Saint Aloysius Roman Catholic Church, serving as an altar boy in his early years, an usher at 7:00 a.m. Mass for decades, and became a 4th Degree member of the Knights of Columbus in 1948. He was appointed a parish trustee by Msgr. McGuire in 1971 and served in that capacity until recently, when he was named a Trustee Emeritus.

Leo is the undisputed and proud patriarch of an expansive family tree. He took a personal interest in each of his 10 children and 22 grandchildren, and their spouses, not only organizing an Annual Karl Family Weekend (which turns into a Karl Family Week every 5 years), but also curating special one-on-one conversations and activities whenever possible.

He loved the outdoors and spent endless hours teaching his kids valuable life lessons, from how to care for perennials, including rhododendrons, azaleas, and hydrangeas, to rotating crops to ensure soil health. He was a renaissance man of many talents, equally adept at tilling a vegetable garden, building a treehouse, pruning trees, landscaping the yard, assembling a stone wall, painting the house, grilling on the barbecue, casting a fly rod, and baking in the kitchen. Leo’s love of travel took him and Kathie on many adventures around the world, and after returning, he proudly hosted slide shows where he would share the sights and sounds of places he had visited and espouse any newly learned tidbits of history and culture.

Beyond his family, Leo was also dedicated to his community. In his mind, a rising tide lifts all boats, and he saw a thriving community as a benefit to all. In his business life, Leo focused on treating employees like family, nurturing not only countless long-term employees, many serving the company for 25 to 40 plus years, but also a consistent and loyal customer base.

One of his proudest accomplishments was the establishment of a company sponsored retirement plan well before they were common in private business. Under his leadership, Karl Chevrolet continued its expansion and growth, surviving multiple gas crises, interest rate spikes, and other external hurdles. He also saw that his business supported a myriad of local causes and organizations. By the time he passed the day-to-day leadership torch to his sons, Leo III and Steve, in 1996, the dealership had earned local, state, and national recognition for outstanding business practices and customer service.

Leo was an incorporator of the New Canaan Savings Bank in 1956, a member of the New Canaan Board of Social Services from 1961 through 2005 (well before anyone heard of term limits!), a member of the Poinsettia Club since 1978 and its President in 1994, a member of the New Canaan Lions Club from 1979 until 2020 and was the Gridiron Club’s “Fall Guy” in 1999. In addition, Leo was named the Chamber of Commerce Man of the Year in 1987, served as a Community Director for Waveny Care Center, was a long-time member of the New Canaan Historical Society’s Board of Governors, was honored by the Friends of St. Aloysius School Foundation in 2006, and was honored by the New Canaan Community Foundation, along with his wife Kathie, with the Spirit of New Canaan Award in 2018. His was a life best described by the phrase “actions speak louder than words.”

Leo was predeceased by his parents, his sister Mary K. Karl, his brothers Henry E. Karl and his wife Marion, Msgr. Edward B. Karl, and Paul R. Karl. He is survived by his wife, Katherine (Kathie), his sister-in-law, Margaret Karl (wife of Paul), and his ten children and twenty-two grandchildren: Leo & Janet Karl III of New Canaan – Melissa and Jessica Karl; Stephen & Tracey Karl of New Canaan – Kevin, Brian, William & wife Jennifer, and Thomas Karl; Joseph & Kathleen Karl of Chester VT – Riley, Paige, and Brigid Karl; Katherine (Karl) & Daniel D’Amato of Denver, NC – Jordan, Brendan, and Casey; Mary Karl of Stratford, CT – Cassidy Nosenzo; Elizabeth Karl of Fairfield, CT – Max and Jack Saunders; Christopher & Reedie Karl of Darien, CT – Lila, Georgia, and Teddy Karl; Sara (Karl) & Spencer Schubert of New Canaan – Cole, Ethan, Jeremy, and Rebecca Schubert; John Karl of Fairfield, CT; and Robert Karl of Fairfield, CT.

Calling hours will be held on Thursday, January 18th at Hoyt Funeral Home in New Canaan from 4:00-8:00 p.m. A Mass of Christian Burial will be celebrated on Friday, January 19th 10:00 a.m. at Saint Aloysius Church in New Canaan. Interment will follow at Saint John’s Cemetery in Norwalk, CT.

Leo loved his community. As such, in lieu of flowers, the family requests donations be made to the New Canaan Community Foundation, c/o the Karl Legacy Fund, 111 Cherry Street, New Canaan, CT 06840. In the coming months, the family will make distributions in our Dad’s memory to non-profits that held a special place in his heart.

For online condolences please visit www.hoytfuneralhome.com.

For live streaming please visit https://boxcast.tv/view/funeral-mass-for-leo-e-karl-jr-eqgjqeag4vdjtjc60uim.