PITTSFIELD, Mass. — Joseph A. DiMassimo, a former construction company executive, property developer and longtime owner of Teo's Hot Dogs, one of Pittsfield's most popular restaurants, died on Nov. 27 at his home with family members at his side and a recording of Frank Sinatra singing in the background. 

He was 92; his favorite Sinatra tune was "My Way."

Mr. DiMassimo, who had lived primarily in North Naples, Fla, since the early 1990s, returned to Pittsfield in early spring of 2023 to recover from injuries he suffered in a fall. His wife, the former Elizabeth "Betty" Tisdale of Clarksburg, whom he married in February 1954, died in 2014. 

One daughter, Dawn Harrison, died in 2020 after a long battle with cancer. She had been her mother's full-time caregiver in Florida for more than a year prior to Betty's death.

In 1994, after moving to North Naples, the couple opened another Teo's restaurant nearby, which they operated successfully for 11 years.

"Teo's South" was the last major venture in Mr. DiMassimo's lengthy and active business career, which began soon after his 1950 graduation from Pittsfield High School. He went to work for his uncle's firm, Virgilio Construction Co. Steadily gaining experience and diversifying his skills – he was particularly adept at drawing and reading blueprints – Mr. DiMassimo oversaw the company's construction of portions of the Massachusetts Turnpike and parking lots for several of Pittsfield's supermarkets, including Bradlees and the Stop & Shop Plaza on Merrill Road, among many others. He could summon technical details of the construction of scores of the city's streets and roads, even those worked on by other contractors, sometimes recalling exact specifications of drainage systems and pavement types and thicknesses. He occasionally regretfully recalled his involvement in the demolition of Pittsfield's Union Station in 1968. He left Virgilio Construction in 1981 as its president/chief operating officer and bought Teo's from its founder, Tilio ("Teo") Bilia.

In 1989, Mr. DiMassimo and a partner purchased the Williams Street site of the former Adams Super Market, which had been vacant since 1986. The Williams Street Plaza was sold to Key Bank in 1994.

A gregarious man who enjoyed regular meetings with friends at Teo's and other landmarks of the city's Lakewood section, Mr. DiMassimo often was to be found at the East Side Cafe on Newell Street, then owned by his sister, Dolores Capitanio and her late husband, Mario. (The cafe was recently sold within the family as Mrs. Capitanio, who is 88, and her children sought to retire.)

An avid sports fan who was particularly fond of baseball – he was a lifelong New York Yankees booster – Mr. DiMassimo believed strongly in the character-building capabilities of local youth sports. Teo's sponsored numerous youth athletic teams in both Pittsfield and Florida for many years. In addition to financial support, Mr. DiMassimo donated countless hours of his time as a Little League coach. He and his wife saw to it that the family was represented at every game being played by their children. In Mr. DiMassimo's book, family was Chapter One.

Joseph Anthony DiMassimo was born in Pittsfield on Aug. 23, 1932, son of Frank and Evelyn Virgilio DiMassimo. The family lived on Newell Street. Mr. DiMassimo's father, a draftsman at General Electric Co., also operated a driving school. More than a few of its pupils were recent immigrants from Italy and benefited from Frank DiMassimo's ability to translate the state driver's license manual into their native language. Joseph DiMassimo and his sister, Dolores, retained a working knowledge of conversational Italian; a younger brother, Francis, died in 1997. In his later years, Joe DiMassimo would occasionally – and unexpectedly -- croon an Italian ballad.

Mr. DiMassimo leaves five children, Debra (Dusty Bahlman) of Williamstown, Joseph Jr. "Jody" of Dalton and his wife, Karen; and Dean DiMassimo, Jill Bean and James "Jamie" and his fiancée, Diane Vogel, all of Pittsfield.

He also leaves his grandchildren: Andrew Harrison, Jennifer (Thuto) Nhlekisana, Amanda Desautels, Nicole, Samantha (Xavier) Pease, Joseph III "Joey," Ashleigh, Gabrielle, Daniel, Josh and Derek.

His great-grandchildren are Ryan, Brandon, Logan D., Hunter, Hadley, Logan C., Addison and Damon.

A great-great granddaughter, Charlotte, and many nephews and nieces also survive.

Calling hours are Wednesday, Dec. 4, from 4 to 7 p.m. at Dery Funeral Home, Bradford Street, Pittsfield. The funeral will be Thursday, Dec. 5, at 10 a.m. in Sacred Heart Church, East Street, Pittsfield. Burial will be in St. Joseph's Cemetery, Pittsfield, following the service.

Donations in Mr. DiMassimo's memory may be made to St. Jude's Children's Research Hospital or Shriner's Hospital in care of the funeral home.