David Stern’s pitch to NBA owners in his pursuit of establishing the WNBA could be summed up with one question: How would you like to own basketball on a year-round basis in your city?
At the time, no one had a tighter grip on the professional basketball landscape than the Chicago Bulls. Even though New York had history and Los Angeles had flash, neither had Michael Jordan. The Bulls were on the verge of completing their second three-peat, but when Jerry Reinsdorf was approached to be involved in the WNBA, he had no interest.
Stern’s goal for the WNBA was not to make it a bus league. He wanted teams in all four time zones and all major media markets. The most significant missed opportunities in the eyes of those fighting to establish the league were Philadelphia, Chicago, San Francisco and Dallas.
The WNBA’s inaugural season in 1997 featured the Utah Starzz, Cleveland Rockers, Charlotte Sting, New York Liberty, Houston Comets, Sacramento Monarchs, Phoenix Mercury and Los Angeles Sparks. Chicago would wait nine years before Stern’s brainchild took root there.
Michael Alter led a group of investors announced in February 2005 as the WNBA’s second independent ownership group and first in a city with an NBA presence. The team had no established infrastructure, name, coach or players, but Alter and his lone employee, then-CEO/president Margaret Stender, got to work to have the franchise ready for its inaugural season in 2006.
2005 - 2007
Stender and Alter’s first order of business was securing a lead sponsor. With no players or coach to sell the product, the league enlisted the help of Lisa Leslie, who flew to Chicago in January of 2005 to join Stender and Alter at a pitch meeting with LaSalle Bank.
“We met her downtown, and she had three coats on,” Stender said. “We had a great presentation, Lisa was incredible and LaSalle said yes and became our first sponsor.”
With no affiliation to the Bulls, the new WNBA franchise was able to come up with its name, color scheme and logo. Stender organized a brainstorming meeting at her house, and the group of about 10 came up with three goals for the name. They wanted it to be unique to Chicago, fit cleanly on a jersey, hat and other memorabilia, and they wanted it to be aspirational. Everything from Chicago food to transportation concepts was thrown around. Nothing stuck until the group began discussing Chicago’s skyline and architecture.
They accomplished all their goals with the name Chicago Sky and brought the logo to life with a sky-blue and yellow color scheme.
In their first three seasons, the Sky had three coaches: Dave Cowens, Bo Overton and Steven Key.
At the expansion draft in November 2005, the WNBA’s 13 teams were allowed to protect up to six players, and the Sky could select one player from each team. In the inaugural season, Cowens’ team won only five games. Overton more than doubled that the next season, but the Sky still finished with a losing record.
Their first winning season wouldn’t come until 2013. In the meantime, they were able to win big in the draft.
With their first-ever draft pick, the Sky selected Candice Dupree sixth overall in 2006. They took Armintie Price the next season with the third pick. She went on to be the Rookie of the Year.
In 2008, the Sky selected their first franchise player.
2008 - 2010
In the early years of the NBA, the league established the territorial pick.
It was a unique draft pick that allowed teams to select a player from a nearby college by forfeiting their first-round selection. Wilt Chamberlain and Oscar Robertson were taken with territorial picks.
The WNBA never established anything similar to the territorial pick, but if it had, the 2008 draft might have gone differently.
Candace Parker was fresh off her second NCAA championship with coach Pat Summitt at Tennessee when the Sparks selected her with the No. 1 pick in the 2008 draft.
The NBA’s territorial draft rules stipulated the player had to play within 50 miles of the team’s arena. Tennessee was well outside that radius from the Sky’s then-home arena at UIC, but many have questioned what a rule that allowed WNBA teams to draft hometown talent could have done to boost the nascent league’s popularity. Parker, who starred at Naperville Central High School, probably would have helped the Sky.
They drafted Sylvia Fowles second overall in that draft, but not before making every attempt to trade up to select Parker.
Fowles, who is set to retire after the 2022 season, helped lead the Sky to the franchise’s best record in 2009 alongside Dupree. Both were named All-Stars, Fowles for the first time and Dupree for the third time.
In 2010, the team moved to Allstate Arena. Key, the Sky’s longest-tenured coach at the time (2008-2010), resigned after another 14-20 season, and the Pokey Chatman era followed.
Chatman, the Sky’s fourth general manager and coach, was reunited with Fowles, whom she had coached at LSU, and led the Sky to two more 14-20 seasons in 2011 and 2012.
As the franchise’s new leader, her first move was selecting Courtney Vandersloot with the third overall pick in the 2011 draft. Fowles became the second player in WNBA history to average a double-double for a season (Chamique Holdsclaw, 2003) and earned her first Defensive Player of the Year award in 2011.
Vandersloot, who set the Sky’s single-season assist record (124) in her rookie year, earned her first All-Star nod, joining teammates Epiphany Prince and Fowles on the Eastern Conference roster.
The Sky won the second pick in the lottery for the 2012 draft and opted to make a trade for a veteran with championship experience.
Three-time WNBA champion Swin Cash arrived in Chicago with Le’coe Willingham from Seattle in a trade for the No. 2 overall pick in the 2012 draft. Before the season started, Chatman added another veteran with championship experience in Ticha Penicheiro, who was the league’s all-time assist leader.
“It came down to Phoenix, San Antonio and Chicago,” Penicheiro said. “I played with [Epiphany] Prince and Diana Taurasi in Turkey, so they were both recruiting me. I knew I was going to play with Sylvia [Fowles] and Courtney [Vandersloot], and that was something I was looking forward to. I was a huge fan of [Vandersloot] and felt like her future was so bright. Clearly, I was right.”
Their 7-1 start to the season was the best in franchise history. But in their seventh year, the Sky again failed to make the playoffs.
2013 - 2014
The Elena Delle Donne years came next after the Sky drafted her with the second overall pick in 2013. Brittney Griner went first to the Mercury.
Penicheiro retired, but the Sky’s roster remained a balanced group with veteran experience and young talent. Chatman signed hometown player Allie Quigley, who was a WNBA journeywoman at that point in her career, playing for four teams in her first four years. Quigley took a year off from the WNBA in 2012 to focus on her overseas career before signing with the Sky in 2013.
The Sky’s talented roster featured Fowles, Delle Donne, Cash, Vandersloot and Prince in the starting lineup and Tamera Young coming off the bench. Fowles won her second Defensive Player of the Year award, and Delle Donne was named Rookie of the Year.
They finished the regular season 24-10, which is still the best record in franchise history, and earned their first trip to the playoffs.
The Sky topped one historic season with another, going to the WNBA Finals for the first time the following year, despite finishing fourth in the conference with a 15-19 -record.
They were outmatched against the Mercury, who, along with Taurasi and Griner, had Penny Taylor, DeWanna Bonner and former Sky All-Star Dupree.
Departures and decline would mark the next few years.
The Fowles era in Chicago ended in 2015 after the seven-time All-Star requested a trade before the season. After sitting out the first half of 2015, Fowles was dealt to the Minnesota Lynx in a three-team trade that landed the Sky All-Star center Erika De Souza from the Atlanta Dream.
Chatman traded Prince to the Liberty for hometown star and two-time WNBA champion Cappie Pondexter, Delle Donne earned her first league MVP award and the Sky finished 21-13. Vandersloot led the league in assists for the first time in her career, and Quigley was named Sixth Woman of the Year.
They were eliminated from the playoffs by the Fever, and Fowles helped lead the Lynx to their third WNBA title.
The Delle Donne era came to an even more abrupt end than Fowles’ era after a thumb injury sidelined her for the last two weeks of the 2016 season.
Delle Donne didn’t play a minute in the Sky’s 2016 playoff run, and they were eliminated by Parker and the Sparks in the semifinals. In her last game in a Sky uniform, Delle Donne lost to her future team, the Washington Mystics, 118-81. Delle Donne played just eight minutes with four points, two rebounds and one block.
After six seasons, Chatman was fired, and reports began to circulate that winter that Delle Donne wanted out of Chicago.
2017 - 2018
Amber Stocks was hired as the Sky’s fifth coach and general manager in December 2016.
As general manager, Stocks made two of the most significant moves in franchise history. She dealt Delle Donne in a trade that brought All-Star center Stefanie Dolson and future WNBA Finals MVP Kahleah Copper to Chicago.
And in 2018, she drafted Diamond DeShields with the third overall pick.
After leading the sky to a 25-43 record in two seasons, Stocks was replaced by a young assistant coach who was touted as one of the best player-development coaches coming up in the league.
2019 - 2021
Nearly two years before James Wade was announced as the Sky’s seventh coach and general manager, Stocks interviewed him to join her staff as an assistant.
Wade was ready to accept the position when Lynx coach and general manager Cheryl Reeve called to interview him for an assistant position on her staff. After flying to Minnesota and interviewing with Reeve, Wade took the job. He spent one year with the Lynx, helping Fowles win her first league MVP award and the team win its record fourth championship.
In his first year with the Sky, Wade was named Coach of the Year, the first in the franchise’s history. He flipped the Sky’s 13-21 record the previous year to 20-14, and for the first time in three years, the Sky were back in the playoffs.
The Sky had three All-Stars — Vandersloot, DeShields and Quigley — ranked second in points and assists and carried a new level of confidence and momentum into the playoffs.
When they lost to the Las Vegas Aces in a second-round, single-elimination matchup, the team felt different than after any previous playoff loss. That was partly because of how the game ended, on an unlikely Vandersloot turnover, followed by a game-winning three-pointer by Dearica Hamby with five seconds left. Another part was that many believed the Sky were the better team.
The 2020 season wasn’t comparable to anything in the Sky’s or the league’s history. All 12 teams traveled to Bradenton, Florida, to play a 22-game season in a bubble environment because of the pandemic.
The Sky were without DeShields and newly acquired forward Azurá Stevens, and they lost to the Connecticut Sun in a first-round, single-elimination playoff game.
In the background, pieces were beginning to align to set up the franchise for arguably the biggest free-agent signing in league -history.
On Feb. 1, 2021, the Sky announced that two-time league MVP Parker had signed a two-year contract to return home. The move made Wade’s team instant title contenders and raised interest in the Sky to levels they hadn’t reached with Fowles or Delle Donne.
The perfect season fans envisioned was far from what took place in 2021.
Wade began the year drafting 19-year-old Shyla Heal from Australia with the eighth pick, trading Gabby Williams to the Sparks after suspending her for the season and then trading Heal to the Wings for rookie Dana Evans. On the court, the Sky’s roster was thin, with players in and out because of national-team commitments and injuries to Quigley and Parker.
After opening the season with two wins, the Sky went on their worst skid since 2012, dropping seven straight games. When Parker returned, the Sky flipped their losing streak into a seven-game winning streak, a franchise record. They carried the best offensive rating in the league into July.
Three Sky players were named All-Stars — Vandersloot, Parker and first-timer Copper — and Quigley won her third career three-point contest. In the second half of the season, the Sky were inconsistent, winning one, then dropping two, going on a three-game winning streak, and then losing back-to-back games on the road.
They lost three of their last four games of the season, following an embarrassing loss to the Aces at home with an 11-point win against the Fever. When the playoffs arrived, nobody knew what version of the Sky would show up. After two single-elimination wins against the Wings and Lynx on the road, it was clear they were ready to contend for a title.
When the Sky opened the semifinal series against the top-seeded Sun with a double-overtime win on the road, whispers about them bringing Chicago its first WNBA title began to swirl. Vandersloot made history in that game, posting the league’s second-ever playoff triple-double, following Sheryl Swoopes (2005). After winning Game 3 at Wintrust Arena to take the lead in the best-of-five series, the Sky closed it out at home.
Six years after being swept by the Mercury in the 2014 WNBA Finals, the Sky were led back by Vandersloot and Quigley, who played in that series, Parker and a young star proving herself to be the future of the organization and league in Copper.
The series was contentious and entertaining and did not lack storylines, from Sky assistant Olaf Lange coaching against his wife, Sandy Brondello, to numerous former teammates in the league and overseas playing on opposite sides. History was all but written when the Sky took the series back to Chicago after splitting games in Phoenix and handily won Game 3.
In front of a sellout crowd for Game 4, the Sky fell behind by 14 points late in the third quarter.
“I just remember thinking, ‘This can’t go back to Phoenix,’ ” said Quigley’s sister, Sam Quigley-Smith. “Their crowd was too loud, too intense to go back to.”
Quigley scored 10 points in the final 11 minutes of the game, invigorating the crowd and her teammates en route to an 80-74 victory and the first WNBA championship for the Sky and Chicago.
The Sky’s first title was met with tears from ownership and players. It was cathartic for the fans who had been with the team from the days at UIC and Allstate Arena and now stood under blue and gold confetti at Wintrust Arena.
Two days later, the team and city celebrated with a parade down Michigan Avenue like Chicago’s championship winners before them.
Wade followed the championship season with another blockbuster free-agency period.
He signed 2019 WNBA Finals MVP Emma Meesseman to join Vandersloot, Quigley, Copper — whom he was able to re-sign — and Parker, who returns for the second and final year of her contract.
Wade once again has his team heading into the season favored to return to the Finals. The history to be made is becoming the third team in the league to win back-to-back titles, which hasn’t been accomplished since the Sparks did it in 2001 and 2002.