They also married the Warren family, descendants of the Earls of Chester several times as well as several of he other well known gentry from the Chesire area. John fits perfectly as how would a 16 year old have the money to get passage with the Winthrop fleet, who were all upper class gentry. I think he may have already been engaged to Mary Warren before he left Wrentham, and he and his sister Elizabeth were most probably with John Warren on the Arabella, with John Winthrop.