Warwick’s Favorite UPS Driver Tom Dempsey Retires

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By Sara Paul

UPS drivers are charged with many responsibilities: secure package delivery, excellent customer service, safe driving and problem-solving skills. Chasing down criminals, however, has never appeared in the company’s job description.

Of course, for Tom Dempsey, simply doing his job was never enough. The Warwick resident and recently retired UPS package car delivery personnel (his formal title) looks back on 35 years of delivering way more than just boxes to the businesses and residents of the Village of Warwick.

At the top of his list of many fond and interesting memories is that chilly day in November of 1990 when a young Dempsey apprehended a suspect who was robbing The Inkwell, then located on Main St. Fearless and strong, Dempsey sprinted after the assailant, tackling him to the ground in the South St. Municipal Lot.

Taking the day off after his heroic pursuit was not an option as it was during the holiday season, and there was much precious cargo to deliver to his loyal customers, his friends.

“I went right back to work. It was the busy season, and those packages weren’t getting delivered otherwise,” laughs Dempsey nonchalantly as he remembers long hours and kind faces.

“I had some great customers. They were all so nice, just like family, and we were together a long time. I loved seeing the same people every day,” recalls Dempsey, who worked 60 hours a week regularly, and 70 hours a week during the holidays. He officially retired on July 31.

A Solid Catholic Education

Born June 6, 1958 in Bayonne, NJ, Thomas Luke James Dempsey moved to Warwick when he was just an infant, with his parents, two sisters and two brothers. Tom’s devout Catholic mom made sure he attended private schools: St. John’s Elementary and John S. Burke High School, both in Goshen.

Work, Love, & Family

After graduating high school in 1976, Dempsey worked for Georgia Pacific for nine years. In 1980, while minding his own business at a little pub in Greenwood Lake called “Giggles,” Dempsey was introduced to a captivating young woman named Darlene. They hit it off immediately and were married that same year.

Dempsey was hired by UPS in 1985.

Kinda Retired

With wife of 40 years, Darlene, daughters, Kelly and Jennifer, and two granddaughters, Harper and Bailey, the “loves of my life,” Dempsey has been enjoying much time spent with his family during his “sort of” retirement.

Unable to hang up his car keys for good, he is currently employed as a full-time delivery person for Corwin’s Florist. Just like his tenure at UPS, this dedicated deliverer of all things is happy to see smiling faces.

Proud to be an American

With family members who have served in branches of the military as well as U.S. government organizations, Dempsey is firmly grounded in his patriotism. He lives by some very simple, but very powerful words: “God Bless America!” 

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Tom Dempsey (right) gathers for a photo with his wife, Darlene & granddaughters, Bailey & Harper.

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Tom Dempsey (middle) is now happy to be delivering flowers for Corwin’s Florist.

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Tom Dempsey (left) is pictured with UPS delivery driver Steve Rice.

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Tom Dempsey (right) with customer & friend Moshe Schwartzberg, owner of Forever Jewelers, on Main St. in 1985.

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Tom Dempsey (right) with customer & friend Moshe Schwartzberg, owner of Forever Jewelers, on Main St, in 2020.


1 thought on “Warwick’s Favorite UPS Driver Tom Dempsey Retires

  1. Tom, despite his limp, always did his best to help. When I attempted to take a heavy item from him he simply said “Just stand back, Les. Tell me where you want it”. He carried my new dehumidifier down to the cellar.
    Frankly, I feel that he deserved retirement years ago but still he carried on, always cheery . Among all his customers I wish mim a happy and long retirement….at last!

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