The Boston Herald archives are available back to 1997 via Gale GeneralOneFile
The Boston Herald archives back to 1991, and Boston Herald blog posts back to 2005, are available through a NewsBank product called NewsLibrary.com. Passes and a la carte purchases may be made through the site.
The Boston Herald library, which closed a few years ago, donated their clipping file archive to the Boston Public Library if you need assistance with articles or photos further back than the 1990s.
Leigh Montgomery
Electronic Resources Librarian
Mass. Trial Court Law Libraries