"Cross said he was a successful machinist before the recession hit and he lost his job and home. He still remembers the day he became homeless: June 5, 2008." 

8 Years later he still cannot find a job and function in society. He can however earn the nickname "The Mayor" among the homeless population, he can sue via the ACLU, he can converse well enough with the journalists interviewing him. Cross seems to like whatever life style he is currently living and is angry that people who have to put up with leeches like him don't want them around anymore.