Pfizer/Trovan was $143m (initially) after trial, maybe 12 years ago. I can’t remember anything that has come close since until this. Adidas was just awarded $305 million against the operator of the Payless store chain, for a three stripe infringement. That’s more than $100m per stripe. If you’re aware of a higher damages award in a trademark case, send it in.
UPDATE: This seems to be a jury trial in the District Court of Oregon, 3:01-cv-01655. The most recent filing indicates that the jurors were in deliberation yesterday and: “Nine juror lunches ordered from the Lotus Cardroom and Cafe, and from Anne’s Deli.” Really, that was on Pacer.
UPDATE: Here is the text of the original complaint.

Read this doc on Scribd: Complaint adidas trade dress 3 stripe