Lindsay Lohan for Lawyer.com

Lawyer.com's decision to feature Lindsay Lohan as a brand ambassador in 2014 backfired spectacularly, as she arrived at the paid launch event just days after missing a court-ordered hearing for a DUI probation violation. The juxtaposition of a celebrity with 28 police arrests endorsing legal services became an instant punchline, generating negative press coverage worth an estimated $5 million in ad equivalency. Compared to Jared Fogle for Subway at #9, this misstep cost less money but produced an even more absurd credibility gap that no amount of media training could bridge.