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Barry Steinberg

Barry Steinberg of Boston, MA, passed away after a long battle with prostate cancer on April 27th, 2021. He was 75 years old.

Barry was born in Port Chester, NY in 1945 to Pearl and Meyer Steinberg. He graduated Port Chester High in 1963 and completed two years of college before being drafted into the Army, serving in Thailand during the Vietnam conflict. After his service,  Barry began a lifelong career in the auto business, initially working for Duddy Kravitz at Duddy’s Tire. In 1974, he partnered with his friend, Albee Stone, founding Direct Tire and Auto Service in Watertown. After six months he bought Albee’s share and they remained lifelong friends. Barry went on to build one of the most well-known businesses in the Boston area, specializing in high-end custom wheels and winning over customers with great service, echoing his father’s motto: “the customer is always right.”  Direct Tire grew to five locations, earning the distinction of receiving the first-ever “Tire Dealer of the Year” by Modern Tire Dealer Magazine, and made Inc. Magazine’s list of “26 Most Interesting Entrepreneurs” for helping to initiate the National Retail Tire Network, a trade group that turned competitors into peers. An advocate for the small business community, Barry helped drive the “Right to Repair Act” into law.

In the 80’s, Barry’s clever marketing phrases, “We’ll Fix It So It Brakes” and “We’ll Brake, Shock & Exhaust You” became hallmarks on Mass Pike billboards. Anyone listening to the radio in Boston was familiar with Barry’s trademark voice touting ads for “Dye-Rect Tire”. Barry broke the mold by working with the Department of Corrections Work Release Program, giving former inmates a chance at employment and livelihood. He was a strong believer in mentoring and training young men and women, folding them into his Direct Tire family, which earned him fierce loyalty over four decades. Many of his friends’ kids got their first job at Direct Tire, including his own three sons.

Support for the community was also close to Barry’s heart. He spearheaded charitable drives for the Boston Food Bank, the Jimmy Fund, Boston Children’s Hospital, as well as Watertown High Robotics Team and Peabody Little League. Barry was a well-known fixture in the Boston area, rarely going out on the town without running into a customer or friend. Barry was the person you called when you were in a jam or just needed advice. He was a hero to his four kids, and it wasn’t just because he doled out free ski lift and concert tickets. He always put everyone else’s needs before his own. Barry had a great sense of humor, and even as a child, he loved entertaining people and making them laugh. He was always a gentleman and positive role model. Up until the end, he maintained a positive outlook on life.

Barry’s greatest passion was his family.  During the blizzard of ‘78, Barry met his beloved wife and best friend, Penny, sparking a 41-year marriage that was the epitome of a joyful, loving, respectful relationship. They shared a love of travel, fine dining (always sitting at the bar!) and a blended family that included his two children – Jason and Matthew and Penny’s – Dan and Sara.  When the grandkids came along, they stole Barry’s heart.  His most treasured moments were time spent with Miranda, Gabriel, Isabella, Claire, Noah, and Logan at the family lake house in Jaffrey, New Hampshire. Swimming, boating, fishing, treehouse building — so many great times over the years. Barry’s happy place was driving his boat at top speed on Thorndike Pond. Then he would cut the motor, sit back with a martini, and watch the sun set behind Mt. Monadnock.

Barry is survived by his wife, four children, and six grandchildren.

Due to Covid, graveside service and burial will be private.

In lieu of flowers, donations in Barry’s memory may be made to Care Dimensions Hospice House in Lincoln or Dana Farber Cancer Institute.


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