Oakes knew everything about Nathan White's family affairs, mostly because Nathan had told him when he was drunk.
Nathan's mom was too obsessed with the perfect romance, but Boss White was a person with a strong career focus.
So Lady White abandoned Boss White and Nathan early on, pursuing her own love.
This led Boss White to be very averse to women, especially those who seemed extremely beautiful and had a presence.
Because Nathan's mom was that type, and Ruby Mercer's looks and presence were very similar to the romantic Lady White.
But just similar, Ruby Mercer is not a selfish person, nor someone who disregards her family.
Boss White has never really gotten to know Ruby, there is some bias which can be erased with familiarity.
But some prejudices that have been etched in the heart cannot be erased no matter what.
And Boss White is such a stubborn, paranoid, obstinate person.
"Actually, Boss White is really looking out for you, it's just that his, um, way is a bit unusual."
