Chicago Sky enter free agency with uncertainty after being upset in playoffs

Connecticut Sun head coach and general manager Curt Miller’s sentiment after Game 5 has the potential to sum up the last five minutes of the WNBA semifinals for the Chicago Sky. Chicago looked like it had secured its second trip to the Finals in as many years, holding a nine-point lead with 4:46 left. By the time the clock hit zero, though, the tide had turned all the way to a nine-point deficit.

The turn of events left the team and fans completely aghast after the game. Everyone had the same “How did we get here?” look on their face as Sky players and head coach and general manager James Wade tried to process what had just happened.

“It really hasn’t sunk in yet,” guard/forward Kahleah Copper said during the team’s exit interviews the following day. “I’m walking around like, ‘It’s time to pack?’ I’m just not ready for this.”

No one at the team’s exit interviews felt ready to suture the wound the Sun had lashed them with the night before. The agony was clear as players were peppered with questions about the future they didn’t think they would have to answer until after the WNBA Finals. As Copper said, if you have an opportunity to do something special, you have to take advantage of it.

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Now confronted by the future, Chicago has a lot to take away from its past. The team is in a comparable position heading into this winter as it was last offseason. Allie Quigley and Candace Parker, who are both free agents, are considering retirement while Courtney Vandersloot, Azurá Stevens and Emma Meesseman can all test the market. Rebekah Gardner is also a reserved free agent after leaving a strong impression on the league as a rookie.

Wade wasn’t fazed when asked about the Sky’s upcoming offseason, saying that it’s the challenge he signed up for.

“Everybody looks at teams that have free agents and say, ‘Wow, what are they going to do?'” Wade said. “… I look at it in a different light. I look at it as, we have money and we can actually construct a great roster because we have available roster spots. I think that is how you have to look at it.”

Outside of building a championship culture, one of the biggest aces in the hole for the front office last offseason was selling players on going for back-to-back titles. It won’t have the same type of pitch this year, but, as Wade slyly put it, he will sell them on “winning two out of three.”

A lot of the decision-making will be dictated by Quigley and Parker.

Quigley likely won’t be playing overseas this offseason after doing so for 14 years. If she does, she said it will likely be with Vandersloot for Sopron in Hungary, where they both qualify as domestic players because they have dual citizenship. Money will also likely impact Quigley’s decision to retire after she took a $59,000 pay cut to return to Chicago last season. The Sky were able to re-sign Copper and Vandersloot and bring in Meesseman because of Quigley’s financial sacrifice.

Relevant to both Quigley and Parker’s decision to go for another ride around the block will be their physical health. The 2023 WNBA regular season is going to be extended to 40 games from 36 this season. Parker told The Next in training camp that she no longer plays five-on-five in the offseason and works with her trainers to stay in peak condition. However, she has had eight knee surgeries in her career and stated that her mindset heading into the 2022 season was that she would retire at season’s end.

Vandersloot, meanwhile, is at the peak of her powers. She was second in the league in assists per game this season (the first time she hadn’t led the WNBA in that category since 2016) and was fifth in assist points created. Any team with cap space and an opening at point guard will want to take a meeting with Vandersloot, who ranks third all-time in career assists. The most obvious option is the Seattle Storm, which not only offers a personal connection to Vandersloot (who is a native of Kent, Washington, and a Gonzaga alum) but also has a nucleus that could win a championship.

Storm point guard Sue Bird may have been indirectly talking to Vandersloot during her postgame interview after her final WNBA game:

Vandersloot said in her exit interview with the media that the WNBA’s prioritization rule, which will take effect next season, will impact her decision to return to the league. Same goes for Meesseman, who said the rule isn’t great for European players like herself. Stevens, who started all 10 playoff games for the Sky a year ago but none this time around, could regain a starting spot if Meesseman and/or Parker are not with the team in 2023. But she will also be enticing to teams as a modern big who can erase shots at the rim and stretch the floor.

The veterans are only one element Wade will have to work into the equation. Dana Evans and Ruthy Hebard both expressed a desire to play bigger roles next year after rarely being utilized during the season.

“I want to be on the court and show what I can do,” Evans said. “I want to be a factor. I don’t want to just be a cheerleader on the bench. I want to be in the game. I want to play.”

Throw reserve point guard Julie Allemand, who said that this season was tough due to not being accustomed to playing a backup role, into the mix and this team will look different next season.

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Chicago’s championship window hasn’t shut yet despite an uncertain future. Wade is evolving from being a coach with a championship into an institution in the league. He has the ability to get through to his team and, after a devastating loss to the Sun, he could very well use it to light a fire for one more run.

“We are going to take our time and try to make pieces match, somewhat like we did this past year,” Wade said. “People look[ed] at us in 2021 at the same time and said, ‘They’re in trouble.’ We ended up having a good team, and so the challenge is for me to do it again. And I’ll be ready.”