Benzine has known her since just after starting running. After the Lincoln Towing job, he went to her and made a donation to the Orc Underground’s clinic. He’d been back several times since, and run into her pretty regularly.
At one point, he’d returned after being abducted by Project Gypsum, and had her give him a physical.
During the Van Casper Clinic job, he reached out to her with a job opportunity. First she thought he was asking her out; she said she was married. But after that, she interviewed, and accepted.
Then, when Harry had found a magic artifact that could cure any affliction, they let Roxy use it. They went to Courtney to check her out first. She was impressed, and was even more impressed when Benzine made a donation right after. He asked her if she wanted to come to the Rhino with them, and she accepted. When Roxy was assassinated, she looked after Castle.