After he won the lottery, Cyrus decided to go looking for Jennifer, who he had shared a weekend with in Atlantic City years before, and had been the only woman he had formed a real connection with.
After he was hospitalized, Jennifer came to visit him, claiming she had been in Virginia when she read about his lottery win and decided to look him up. When she said she had to return home, Cyrus agreed to pay for a hotel for a few days. Jennifer agreed to stick around.
However, Thirteen immediately got suspicious of Jennifer's motives. She noted that she came to the hospital in a new outfit the next day, even though she said she was only planning to be there for the night. She was afraid Jennifer was merely there to get Cyrus's money.
When Cyrus got worse, he wanted to ensure that Jennifer was taken care of. However, she urged him to take care of people closer to him. As such, Cyrus soon started to give his cousin Phil $10 million. However, he started to become suspicious when he noticed Jennifer was wearing contact lenses that changed her eye color. He asked her where the nickname "Baby Bear" came from and when she couldn't answer, he realized she wasn't the real Jennifer and sent her away.