A more minor part of Roy's character development has been how he has come to more fully like and respect his team. I think he always took his responsibilities as a leader seriously, and tearing up the contracts was an important symbolic first step in his changing attitudes, but Roy continued to judge his teammates pretty harshly for their faults for a while, even as he simultaneously gained more respect for their loyalty and (mostly) good intentions.
Also, she's his girlfriend. A lot of otherwise stand-up guys will keep their mouth shut to avoid rocking the boat. Particular if you spend the vast majority in a party (but for Haley) of the sausage variety.