This is your cousin, Tory. I've been digging around online about Winthrop and have found some information. He, Ira, and a sister names Lucinda were at Tewksbury Almshouse in 1890. I found this through the UMass Lowell Library Archives (online). I haven't found out anything else about why they were there or how long they were there.
Also, Google News has news articles from 1910 documenting Winthrop's arrest on July 4, 1910. He stole "pork loins and other goods" from a train. He was held on bail for $500. At his court hearing, he plead guilty and was sentenced to 7 months in jail. The article says, "Pocknett seemed indifferent as a result of the hearing on his case and told willingly that he hailed from Mashpee."
I wonder if there are records of his jail time? I am also interested in seeing a death certificate or a marriage certificate. I remember bits and pieces of stories that Grandma T talked about; my father knows more.
I realize your post is over 13 years old, and perhaps you know this already. If you have found anything else over the years, I would be very curious to know too.
Hope you are well-