A Career in the Family Insurance Business
James P. “Jimmy” Daley, a longtime member of the Massachusetts insurance industry who followed his father into the family-owned T.P. Daley Insurance Agency in West Springfield, passed away peacefully on Wednesday, October 21, 2026, surrounded by his family. He was 66.
Born in Springfield to the late Thomas P. and Joan E. (Manning) Daley, Daley grew up in Springfield and West Springfield. He attended St. Thomas the Apostle School and graduated from Cathedral High School in 1977, where he was a championship sprinter.
He subsequently attended American International College, earning a bachelor’s degree in business.
After college, Daley joined T.P. Daley Insurance Agency, following in his father’s footsteps. Over the course of his career, he learned all aspects of the family insurance business and became a familiar presence at the agency.
His involvement in the insurance industry also played an important role in his personal life. In 1986, while attending a National Association of Surety Bond Producers (NASBP) Bond School in Houston, Texas, he met his future wife, Rosalie “Rosie” Staton. The couple married in 1988.
Daley maintained a close connection to the family agency throughout his life. His yellow Labrador retriever, Tucker, became a regular companion and the agency’s official greeter.
Family, Motorsports, and Community
Outside the insurance business, Daley was an enthusiastic automobile and motorsports fan. His interest in sports cars began during his teenage years, when he owned Corvettes and Datsuns, and continued throughout his life.
He was particularly devoted to the Indianapolis 500, attending the race each May and following the drivers and competition closely.
Daley also enjoyed golf, fishing, and snowmobiling, often traveling with his brother and close friends. As his children grew up, he devoted considerable time to coaching their soccer and basketball teams.
Family remained central to his life. He especially enjoyed spending time with his five grandchildren and was looking forward to the arrival of a sixth grandchild in December.
Survivors and Funeral Arrangements
Daley is survived by his wife of 38 years, Rosalie (Staton) Daley; his sons, Ryan (Courtney), Kellan (Kaitlynn), and Brendan (partner Marion); and his daughter, Meghan Shibley (Brett).
He also leaves five grandchildren: Miles, Piper, Cooper, and Rosalie Shibley, and Ledger Daley.
Other survivors include his siblings, Anne Klejna (Joe), Kathleen Daley, and Thomas Daley (Claire), along with numerous nieces, nephews, and members of the extended Daley and Staton families.
Visiting hours will be held Thursday, October 29, from 4:00 to 7:00 p.m. at Curran-Jones Funeral Home in West Springfield. A celebration of his life will take place at the funeral home on Friday, October 30, at 11:00 a.m.
In lieu of flowers, the family requests that donations be made to the Dana-Farber Cancer Institute.
Mr. Daley’s obituary can be viewed on the Curran Jones Funeral Home website here.
