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.
(..) Yay! What? No, no "yay". Ramsbottom didn't say anything about a partner. Well, it seems that because of your checkered past, everyone else refused to work with you. But not me. I stepped up. And I'm new, so I kind of have to do what they tell me anyway. (..)2013 Despicable Me 2
(..) There at the end of the runway, at the end of the ramp, rather, was Jeffrey's father, smiling, well-tanned, little red, white and blue checkered golf pants on, short-sleeved shirt. And Jeffrey's mother handed Jeffrey to the father and punched him dead in the face. We don't know why. (..)1983 Bill Cosby: Himself
(..) 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