Diamond DeShields currently plays for the Chicago Sky, marking her return to the team where she first made history as a WNBA champion. Drafted as the No. 3 overall pick in the 2018 WNBA Draft from the University of Tennessee, Diamond quickly established herself as a force on the court. In her rookie season, she reached her 1,000th WNBA career point, highlighted by a career-high 30-point performance against the Connecticut Sun. She also made her mark as a WNBA All-Star in 2019, winning the Skills Challenge during All-Star Weekend and earning a spot on the All-WNBA Second Team.

Diamond's journey took a dramatic turn in December 2019 while playing overseas in Italy. After suffering a back injury, an MRI revealed a tumor on her spine, which carried the severe risk of permanent paralysis. Undergoing surgery to remove the tumor, Diamond faced months of intense rehabilitation, battling tremors and involuntary spasms that left her uncertain if she would ever return to the game she loved. She chose to keep her ordeal private until sharing her story in an exclusive ESPN interview with Holly Rowe.

Despite her challenges, Diamond returned to the court with determination. In the 2020 WNBA season, she navigated the bubble environment amidst the COVID-19 pandemic, though her play was limited due to her ongoing recovery. By 2021, she regained her form, averaging 26.9 minutes and 11.3 points per game, and played a crucial role in leading the Chicago Sky to their first WNBA championship. The Sky secured the title in a thrilling four-game series against the Phoenix Mercury.

In 2022, Diamond continued to make her mark, joining the Phoenix Mercury and quickly becoming a key contributor, averaging 27.8 minutes and 15 points per game. Now, back with the Chicago Sky in 2024, she remains a vital presence both on and off the court.

Diamond's athletic prowess is deeply rooted in her family. Her mother, Tisha DeShields, was a standout heptathlete at the University of Tennessee. Her father, Delino DeShields Sr., enjoyed a 13-season career in Major League Baseball and is currently a coach for the Cincinnati Reds. Her brother, Delino DeShields Jr., plays as a center fielder for the Atlanta Braves.

Beyond her achievements on the court, Diamond is also committed to making a difference off the court. Through her philanthropic efforts, she strives to empower underserved communities, focusing on initiatives that provide eye care, mentorship, and opportunities for growth, reflecting her belief in the power of vision—both literally and metaphorically.