American Veteran 04

Robert G. DePippo

November 26, 1938 ~ January 21, 2022 (age 83)

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Bob DePippo, known by everyone as "Puppy", was a longtime Winthrop Resident. He was the son of the late William and Constantina DePippo. He graduated from Winthrop High School Class of ‘57. He played WHS football where he excelled as a fullback, compiling numerous write-ups in the newspapers highlighting his successful career. After high school he enlisted and served in the Marine reserves for six years.  

Puppy was known to many as an extension of their own family for many of his children’s friends, nieces, nephews and their children. He was informally known as “Pup”. He was a regular at the Center Coffee Shop and each morning he looked forward to meeting up with his friends at French Square, which he always referred to as “Shady Acres''. They caught up on all the latest gossip and reminisced on old times. He was an avid Patriots fan and never missed the opportunity to attend the games at Gillette Stadium with his family. 

Pup had a zest for life, a twinkle in his eye along with a sly smile. He and his wife Susan opened  their home on South Main Street to everyone with 4th of July pool parties, Christmas and Super Bowl gatherings for close to four decades. If you came to their home, you instantly felt like family. He adored his wife Susan with whom he shared 39 years of marriage and loved his four Children.  He was especially proud of his Grandchildren. He happily attended all their sporting events, dance recitals, award ceremonies, birthdays and graduations with pride and admiration.  

He was employed by United Airlines for over 35 years and upon retiring was honored with a special dinner in Washington DC, recognizing him as ‘Employee of the Year’. During his retirement he and his wife traveled by cruise to so many places, Alaska being his all-time favorite. He would light up telling the story of the 28-mile rail excursion that descended over the White Pass Summit and into Skagway, then shop, have lunch, or just stroll around the unique and historic area.  Just as much as friends and neighbors adored him, he was absolutely loved by his wife and his four children. Pup was a wonderful husband, father, grandfather, uncle, and friend who always put the needs of everyone else first. He will be sorely missed by all who had the privilege of knowing him. 

He leaves behind his Wife, Susan DePippo (Trainor) of Winthrop. His Children: Robert DePippo and his partner Adele Centola of Topsfield. Michael DePippo and his wife Margaret of Swampscott. Patty Cresta and her Partner John Donovan of Salem, NH and Barbara Cole and her Husband Greg of Hamilton. Grandchildren: Christopher Cresta, Jennifer Cresta, Stephanie Cresta, James Evans, Jessica Rich and her husband Carmen, Capria Cole, Amanda DePippo, Michael DePippo, Stephanie, and Pete DiOrio and predeceased by his granddaughter Julia Evans and his brother the late William DePippo. Great Grandchildren: Anthony Cresta and Sophia Cresta. Brothers: Thomas DePippo and his wife Dolly of Florida. Richard DePippo and his wife Fran of Florida.

Family and friends are cordially invited to attend the visitation from the funeral home on Thursday, January 27, 2022 from 4:00 to 8:00 PM. The funeral will be conducted from the funeral home on Friday, January 28, 2022 at 9:00 AM followed by a funeral mass in St. John the Evangelist Church 320 Winthrop St., Winthrop at 10:00 AM. Interment will be private.  

In lieu of flowers, the family asks donations to be made to his favorite charity, The Jimmy Fund, in honor of his late granddaughter, Julia Evans. 

To send flowers to the family or plant a tree in memory of Robert G. DePippo, please visit our floral store.


January 27, 2022

4:00 PM to 8:00 PM
Ernest P. Caggiano & Son Funeral Home
147 Winthrop Street
Winthrop, MA 02152

Mass of Christian Burial
January 28, 2022

10:00 AM
St. John the Evangelist Church
320 Winthrop St.
Winthrop, MA 02152


The Jimmy Fund, Dana-Farber Cancer Institute
10 Brookline Place, W 6th floor, Brookline MA 02445
Tel: 1-800-525-4669

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