Context #1
Tom: Did you hear about the new class action law suit against the Paypal?
Chris: Yeah, but big companies like that don't care.
Tom: You're right. They have such deep pockets that they can just pay people and move on.
Context #2
Jennifer: I heard that Sarah's company is sending all the employees on a free cruise to Hawaii.
Kathy: Yeah I know! But don't worry. Her company has really deep pockets. They can afford it!
Meaning: to have deep pockets is an idiom used mainly for a company or corporation. It means that they have massive, almost limitless, financial resources.
