This is James "Spike" O'Toole, Dorchester gangster. d.o.b. 12/7/29
He was set up by Eddie Connors who would later be machine-gunned in a telephone booth by Whitey. O’Toole, having survived numerous assassination attempts over the years, was staggering out of the Bulldog Tavern on Savin Hill Avenue one night in December 1973 when Johnny Martorano mowed him down and then jumped into a gold car that took off towards South Boston.

Herald Advertiser Article 12/2/73

Spike had two children by his moll, Dorothy Barchard, the one-time wife of one of Whitey’s bank-robbing gang.  She wanted child support in 1965.
PM Boston Globe article 3/16/65

Dorothy Barchard was also allegedly involved with John Fitzgerald, Joe Barboza's attorney whose leg was later blown off in a gangland assassination attempt.

 

Congressional Investigators account of how the Mafia offered to kill O'Toole in prison as a favor for Fitzgerald.