When it comes to labor relations, the company has a somewhat 'checkered history'. [=the company has sometimes had problems with labor relations]
The senator has a 'checkered past'. [=he has done bad things or been in trouble in the past]
He has had a 'checkered' career with many ups and downs.
(..) Yeah, but... Let's do who you are minus the hornet stings. Let's pretend you're not who you are and just try to attract a woman. I tell you what. What if I wore a checkered hat and I smoked a pipe? That'd work. Why would you want a checkered hat and a pipe? You know, for the Sherlock Holmes look. (..)2009 TvShow: It's Always Sunny in Philadelphia Title: The Waitress Is Getting Married Season: 5 Episode 5