Last Updated on March 15, 2026 by Mat Diekhake

Chicago Sky history has been shaped by franchise-record setters, MVP-level stars, championship pillars and long-term culture builders. The strongest cases start with the players who either owned the franchise statistically, lifted Chicago to historic postseason breakthroughs, or defined the Sky across multiple eras, from the early Candice Dupree-Sylvia Fowles years to the 2021 title core led by Courtney Vandersloot, Allie Quigley, Candace Parker and Kahleah Copper. (Chicago Sky)

1. Courtney Vandersloot

  • Years with Chicago Sky: 2011–2022, 2025
  • Position: Guard
  • Notable achievements:
    • 2021 WNBA champion
    • Five-time WNBA assists leader while with Chicago
    • Longtime franchise floor general
    • One of the defining players in team history

Vandersloot gets the top spot because no player has been more synonymous with Chicago Sky basketball over time. The Sky’s official 2025 return announcement called her a franchise great and noted that in her 12-year tenure she led the league in total assists in five seasons from 2015 and 2018–21, while helping lead Chicago to the 2021 championship. Her longevity, playmaking identity and central role in the title era give her the strongest overall legacy case. (Chicago Sky)

2. Sylvia Fowles

  • Years with Chicago Sky: 2008–2014
  • Position: Center
  • Notable achievements:
    • Franchise all-time leader in multiple major categories during her Sky run
    • Elite rebounder and rim protector
    • Multiple-time All-Star and Defensive Player of the Year-level force
    • Foundational star of the franchise’s first strong era

Fowles has a real No. 1 argument based purely on dominance. Chicago’s official top-10 history feature says she became the franchise leader in seasons played, games played, minutes, points, rebounds, free throws made, field goals made, career rebounding average and rebounds in a game, and described her as the cornerstone of the Sky for seven seasons. That kind of statistical and stylistic control is rare in franchise history. (Chicago Sky)

3. Allie Quigley

  • Years with Chicago Sky: 2013–2022
  • Position: Guard
  • Notable achievements:
    • 2021 WNBA champion
    • Jersey retired by Chicago
    • Four-time WNBA 3-point contest champion
    • Three-time WNBA All-Star

Quigley ranks this high because she combined longevity, shot-making and championship value with franchise-icon status. Chicago officially moved to retire her No. 14 jersey in 2025, and the team also highlighted her historic fourth 3-point contest title in 2022. Her Sky résumé includes elite perimeter shooting, multiple All-Star appearances and a major role on the championship team, which is more than enough to put her in the top tier. (Chicago Sky)

4. Elena Delle Donne

  • Years with Chicago Sky: 2013–2016
  • Position: Forward
  • Notable achievements:
    • 2015 WNBA MVP
    • First Sky player to win league MVP
    • Led the WNBA in scoring in 2015
    • Face of Chicago’s first true superstar era

Delle Donne’s Sky peak was too powerful to rank lower. Chicago’s official 2015 season review says she became the first player in franchise history to win the WNBA MVP award, led the league in scoring, averaged 23.4 points, 8.4 rebounds and 2.0 blocks, and drove the team to a 21-13 record and the No. 2 seed. Even though her Sky stay was shorter than some others, the MVP peak carries enormous weight. (Chicago Sky)

5. Candace Parker

  • Years with Chicago Sky: 2021–2022
  • Position: Forward
  • Notable achievements:
    • 2021 WNBA champion
    • Jersey retired by Chicago
    • Homecoming star on the first title team
    • One of the most important short-term additions in team history

Parker ranks this high despite only two seasons in Chicago because her impact was franchise-changing. The Sky’s official jersey-retirement announcement called her a franchise legend, and Chicago’s 2025 coverage again emphasized that she was instrumental in the team winning its first WNBA championship. Her résumé with the club is short, but the title significance is massive. (Chicago Sky)

6. Kahleah Copper

  • Years with Chicago Sky: 2017–2023
  • Position: Guard/Forward
  • Notable achievements:
    • 2021 WNBA Finals MVP
    • 2021 WNBA champion
    • Multiple-time All-Star
    • Go-to scorer during the title window

Copper belongs in the top six because she was the explosive scoring engine of the championship run. Official WNBA coverage says she won 2021 Finals MVP after averaging 17.0 points and 5.5 rebounds in the series, and Chicago later noted that she helped guide the Sky to their first WNBA title while earning Finals MVP honors. That combination of peak playoff value and multiple All-Star-level seasons gives her a strong legend case. (WNBA)

7. Candice Dupree

  • Years with Chicago Sky: 2006–2009
  • Position: Forward
  • Notable achievements:
    • First-ever Sky draft pick
    • Early franchise star
    • One of the team’s first major scorers
    • Helped establish the Sky in their expansion years

Dupree deserves a spot because she was one of the first players to give the franchise real offensive credibility. Chicago’s official top-10 feature identifies her as the team’s first-ever draft pick, and the team’s 2007 history recap says she scored 544 points that year, averaged 16.5 points and 7.7 rebounds, and ranked among the league’s top 10 scorers. She was central to the early identity of the franchise. (Chicago Sky)

8. Tamera Young

  • Years with Chicago Sky: 2009–2017
  • Position: Forward
  • Notable achievements:
    • Long-tenured Sky veteran
    • Top-10 in franchise history in numerous categories
    • Two-way wing presence across multiple playoff seasons
    • Important culture and continuity piece

Young makes the top 10 because her value goes beyond headline awards. Chicago’s assistant-coach announcement in 2024 noted that she ranks in the top 10 in Sky history in 10 categories, including games played, steals and points. That kind of long-term presence matters for a franchise list, especially for a player who helped connect multiple eras of Sky basketball. (Chicago Sky)

9. Diamond DeShields

  • Years with Chicago Sky: 2018–2021, 2024
  • Position: Guard/Forward
  • Notable achievements:
    • 2021 WNBA champion
    • 2019 All-WNBA Second Team
    • 2019 WNBA All-Star
    • Dynamic transition and wing scorer during a major rise period

DeShields earns this spot because her peak with Chicago was electric and important to the team’s climb into contender status. Chicago highlighted her 2019 All-Star form and her 2024 season review noted that she helped the Sky win their first championship in 2021. She did not have the longevity of some others, but at her best she was one of the most explosive perimeter players the franchise has had. (Chicago Sky)

10. Cappie Pondexter

  • Years with Chicago Sky: 2015–2017
  • Position: Guard
  • Notable achievements:
    • Former WNBA superstar who added major credibility
    • Top20@20 honoree mentioned during her Sky period
    • Veteran backcourt force on playoff teams
    • One of the most accomplished names ever to suit up for Chicago

Pondexter makes the list because even though her prime came before Chicago, she still gave the Sky high-end veteran star power in an important stretch. The Sky’s retrospective on her career emphasized her elite scoring pedigree and postseason stature, and Chicago’s 2016 season history noted that she was among the players honored in the WNBA’s Top20@20 celebration. She was not a franchise-defining Sky lifer, but she was still a major figure in team history. (Chicago Sky)

Strong honorable mentions

  • Erika de Souza
  • Emma Meesseman
  • Stefanie Dolson
  • Jia Perkins

The hardest cuts were de Souza and Meesseman. De Souza was a major frontcourt piece on the 2014 Finals team and one of the stronger veterans of that era, while Meesseman gave Chicago an All-Star season on the 2022 team that followed the title run. Dolson also has a strong case because she was part of the 2021 championship core. (Chicago Sky)

Sources:

Chicago Sky — Courtney Vandersloot returns to Chicago / franchise-great profile. (Chicago Sky)
Chicago Sky — Chicago Sky Top 10 Players. (Chicago Sky)
Chicago Sky — Sky to Retire Allie Quigley’s No. 14 Jersey on July 9. (Chicago Sky)
Chicago Sky — Elena Delle Donne Named 2015 WNBA MVP. (Chicago Sky)
Chicago Sky — 2015 Season in Review: Elena Delle Donne. (Chicago Sky)
Chicago Sky — Sky to Retire Candace Parker’s No. 3 Jersey on August 25. (Chicago Sky)
WNBA — Chicago Wins First WNBA Title With 80-74 Win Over Phoenix. (WNBA)
WNBA — Inside the Box Score: 2021 WNBA Finals, Game 4. (WNBA)
Chicago Sky — Chicago Sky Re-Sign WNBA All-Star and WNBA Finals MVP Kahleah Copper. (Chicago Sky)
Chicago Sky — Chicago Sky Top 10 – Candice Dupree. (Chicago Sky)
Chicago Sky — Chicago Sky Welcome Back Tamera “Ty” Young as Assistant Coach. (Chicago Sky)
Chicago Sky — Diamond DeShields’ 2024 Season in Review. (Chicago Sky)