In 2008, the city of Boston issued a permit for the nineteenth Freedom Rally that sought to cut-off funding for the event by redirecting donations from food vendors at the rally away from Mass Cann/NORML and to the Boys and Girls Clubs of Boston instead.
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Concurrent to her work with the Boston Tea Party Freedom Rally, Whalen became an organizer for Congressman Ron Paul's 2008 presidential campaign in Massachusetts and was also involved in launching the Boston Ron Paul Meetup Group.
Whalen was one of the original organizers of the Boston Tea Party Freedom Rally held on December 16, 2007, at Faneuil Hall in Boston, Massachusetts; Rand Paul was the keynote speaker at this event.