Originating from the same "Whitey and Chip" collection featured in Lelands' Spring 2021 Classic, this set of letters is in the distinctive hand of noted mobster James "Whitey" Bulger. The trio of letters span about 11 handwritten pages (front and back) with some printed material as well spanning from 2014 to 2017, all in black ink and signed by Bulger. One from September 2016, decries the plight of his long-time girlfriend, Catherine Greig Day, who was sentenced to nearly a decade in prison for harboring the fugitive crime boss and refusing to testify against him. Another, from October of 2017, is addressed, "Hello Chip" and discusses books about Alcatraz and again touching on the unfairness of Greig Day's sentence. The earliest is from December of 2014, is addressed "Dear Rose," and provides an update on his "travels," including his preference for the prison in Tuscon, Arizona ("Prefer Tuscon because of all the yard time I enjoyed there - plus I made some good friends there") while mentioning other famed crime bosses such as Machine Gun Kelly and "Mob Boss of Chicago Al Capone." More fascinating content from the man who spent 16 years on the FBI's Most Wanted list, considered second in importance only to Osama Bin Laden in the early 2000's.