The day after her 22nd birthday, Herrington was chosen with the third overall pick by the Chicago Sky, an expansion team of the WNBA. Herrington became the first Ole Miss player selected in the first round of the draft's eleven-year history. She is also just the second Lady Rebel to be selected in the draft (Saundra Jackson was a third-round pick in 2002). On September 8, 2007 Herrington was named 2007 WNBA Rookie of the Year.
