PHOTO THREAD: Joe Mac, Jimmy Sims & the Winter Hill Gang

Here’s a collection of rare shots, FBI charts, and old documents from the days of Joe Mac, Jimmy Sims, and the Winter Hill Gang — along with the book Don’t Talk About Joe Mac by Springs Toledo.

Winter Hill Gang chart
Joe Mac, Howie Winter and Jimmy Sims
Joe Mac, Howie Winter and Jimmy Sims
Joe Mac’s FBI narrative
Joe Mac’s FBI narrative
Joe Mac circa 1972
Joe Mac circa 1972
Jimmy Sims’ FBI narrative
Jimmy Sims’ FBI narrative
Jimmy Sims under arrest, 1974
Jimmy Sims under arrest, 1974
Jimmy Sims, student at Worcester Commerce High School, 1954  
Jimmy Sims, student at Worcester Commerce High School, 1954  
Joe’s wanted poster that he signed for the NYPD cops arresting him in 1982 at Penn Station.
Joe’s wanted poster that he signed for the NYPD cops arresting him in 1982 at Penn Station.
Joe Mac’s notebook with the unnamed Sims entry at #5.
Joe Mac’s notebook with the unnamed Sims entry at #5.
Classified Boston Herald ad from from February 1992, in which Joe McDonald was seeking “Jimmy S. of Winter Hill” to pass on some “Important news for him.”
Joe with his brothers, 1942
Joe with his brothers, 1942
Joe’s Winter Hill residence at 40 Marshall Street, 2022
Read the story behind these photos & more in Don’t Talk About Joe Mac by Springs Toledo.
Read the story behind these photos & more in Don’t Talk About Joe Mac by Springs Toledo.