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One position to be a permanent lawyer is won by Alicia Florrick.
Then he is working for the state's attorney's office.
This soured their relationship until their cleared the air in "We the Juries", after Cary played a trick on Kalinda by exploiting her ambivalent loyalties.
He eventually entered into a sexual relationship with Kalinda and considered her to be his girlfriend.
Things do not look good for Cary and he agrees to take a 4 year guilty plea offered by the SA office.
This act greatly impresses Cary, who tells Alicia, "It's in my nature to be competitive, but I don't want you to lose." Alicia does eventually win the competition, and Cary finds himself out of a job.
Kalinda refuses to be in a monogamous relationship with Cary that leads him to break it off with Kalinda while still calling her his girlfriend.
Kalinda went out of her way to assist Diane and the firm with Cary's drug charges and ended up committing a felony in order to clear Cary's charges. His career path towards becoming a lawyer was not so smooth.
In season 4 "Running with the Devil" it is suggested that their relationship progressed beyond a platonic one.
As Cary and Alicia plan to leave Lockhart/Gardner, Kalinda walks a fine line being loyal both to her firm and her friend, but eventually betrayed Cary in "Hitting the Fan".