Chicago Sky just finished the 2nd-worst season in franchise history. What comes next?

The second-worst season in Chicago Sky history ended in protest Thursday night.

The Sky fell to the New York Liberty 91-86, their 34th and final loss of the season in front of a Wintrust Arena crowd filled to the brim with frustration. The team’s in-house camera operators struggled to highlight fans on the jumbotron without catching glimpses of signs relaying negative messages to ownership, including “Free #5” and “We’re tired of mediocrity #selltheteam.” Midway through the third quarter, the entire arena rumbled with echoing chants from fans calling for general manager Jeff Pagliocca to be fired.

The 10-34 (.227) finish under first-year coach Tyler Marsh isn’t quite the worst in Sky history — that label still belongs to the inaugural 2006 team, which won only five of 34 games for a .147 winning percentage. But the Sky hadn’t ended with a record below .325 since then.

The Sky never had put fans through 34 losses — 16 at home — before. They hadn’t missed the playoffs in consecutive years since 2018. And despite back-to-back dismal seasons, the odds are 5-1 that the Sky won’t land a top-four draft pick.

So what comes next? Here are a few pressing questions as the Sky transition into a pivotal offseason.

When is the expansion draft?

The WNBA has yet to announce dates or rules for the upcoming expansion draft for the additions of the Toronto Tempo and Portland Fire for the 2026 season. The expansion draft is expected to take place this fall, but that leaves a litany of questions unanswered for teams heading into the offseason.

Which franchise will pick first? How many players will teams be allowed to protect? Will teams be able to core a player — as a protection from expansion selection — even though this draft is expected to take place before free agency opens?

The expansion draft will be a crucial turning point of the offseason for the Sky, who are expecting a hefty amount of roster turnover from 2025 to ’26.

When is the draft lottery?

Similarly, the WNBA has not announced the date for the draft lottery.

The Sky do not own their first-round pick in the 2026 draft, which was traded to the Minnesota Lynx through a series of deals to secure the draft picks later used to select Angel Reese in 2024 and Hailey Van Lith in 2025. However, they will receive a lottery pick conveyed from the Connecticut Sun due to a previous deal made with the Sun and Phoenix Mercury.

Angel Reese wants the Chicago Sky to do more in WNBA free agency: ‘We can’t settle for what we have this year’

This means the Sky’s draft position in the first round ultimately will be determined by where the Sun land in the lottery. The Sun have the worst odds of the five lottery teams, giving the Sky an 83.7% chance of receiving the No. 5 pick — which would place them too low to land top prospects Azzi Fudd, Olivia Miles and Lauren Betts.

The Sky’s current positioning also gives the Lynx the strongest odds of landing the No. 3 pick — and a 25% chance of getting the No. 1 pick.

When does free agency begin?

The negotiation period of free agency typically opens Jan. 1 with a moratorium on unrestricted signings until Feb. 1.

Who is still under contract with the Sky?

The only players who will remain under contract with the Sky are the four still on their rookie contracts: Reese, Van Lith, Kamilla Cardoso and Maddy Westbeld. The remaining eight players — including veterans Ariel Atkins, Courtney Vandersloot and Elizabeth Williams — will be unrestricted free agents this winter.

What is the deadline for CBA negotiations?

Each of these questions hinges on the answer to this final uncertainty: What is going to happen in negotiations for a new collective bargaining agreement between the WNBA and players association?

The official deadline for an agreement is Oct. 31. It’s likely the sides would agree to an extension — for either 30 or 60 days — if a deal is not reached by then. But if neither a deal nor an extension is announced by that date, the league could enter into a lockout.

This complicates every aspect of the offseason. If players are locked out, the league can’t hold an expansion draft. Or open free agency. Or host a draft. There is a strong precedent for work stoppages across other major American sports leagues, but the WNBA has never entered into such a situation before. The decisions made in those negotiating rooms ultimately will determine the course for the rest of the offseason.