If suffering were currency, the Chicago Sky would be billionaires by now. For two straight years, they’ve stumbled, collapsed, and invented new ways to break their fans’ hearts. Drafting Angel Reese — the most electrifying, marketable rookie they’ve had in years — was supposed to be the reset button, the beginning of a new Chicago renaissance. Instead, it has become something else entirely: a flashing red warning sign that the franchise may be spiraling toward a full-blown identity crisis.
Reese hasn’t been shy about expressing frustration. She’s called out the “lack of support” and the “unfair load” she’s been carrying on the court. Chicago has missed the playoffs for two consecutive seasons, leaving her to shoulder both the blame and the burden. Suddenly, her future — once viewed as the foundation of a long-term rebuild — is now a question mark, bolded and underlined.
And as if fate weren’t cruel enough, all the losing didn’t even help them.
Despite their collapse in 2025, the Sky’s chances at landing the No. 1 pick in the 2026 WNBA Draft took a hit thanks to a series of questionable front-office decisions. The team swapped pick rights with the Minnesota Lynx in 2024 to draft Reese at No. 7, then surrendered full ownership of their 2026 first-rounder to Minnesota so they could select Hailey Van Lith at No. 11 in 2025.
What they do have — mercifully — is the Connecticut Sun’s first-round pick, acquired in a 2024 Marina Mabrey trade. That pick gives the Sky a 5.5% chance of winning the 2026 draft lottery on Nov. 23. Not great odds. But at this point, Chicago would take “not great” over “catastrophic.”
Still, the hard truth remains: even the No. 1 pick might not save them.
It might help. It might spark hope. But “saving the Angel Reese era”? That’s a taller order.
The towering UCLA star is one of the most coveted prospects in the upcoming class. She’s efficient, polished, and imposing — everything a struggling team wants in a franchise anchor. Could she coexist with Angel Reese and Kamilla Cardoso? Maybe. Maybe not. But when a roster is this thin, the Sky can’t afford to overthink fit. Betts would immediately strengthen Chicago’s weak interior and give the team something it desperately needs: stability.
If Chicago wants the safest pick in the draft, this is it. Olivia Miles is a floor general with elite vision and production — averaging 17.5 points and 7.8 assists at TCU. She’s the kind of guard who elevates everyone around her, including Reese… assuming she stays. Even if she doesn’t, Miles is talented enough to be a franchise reboot by herself. Chicago has lacked a true orchestrator, and Miles could change that on day one.If the Sky draft Flau’Jae, it becomes a reunion headline before she even signs the contract. The pairing of Reese and Johnson would be must-watch TV — flashy, explosive, charismatic. But it’s not just vibes. Johnson is averaging 17.2 points, 4.8 rebounds, and 3.8 assists, proving she’s more than a mixtape star. She’d be a day-one starter and an instant marketing boom for a franchise starving for relevance.
The Sky don’t just need talent — they need clarity. They need direction. They need Reese to believe the franchise is capable of building something, anything, around her.
If they land the No. 1 pick AND repair their relationship with Reese, Chicago finally has the chance to pivot out of chaos.
If they fail at both?
Then a teardown, a rebuild, and a new identity might be the only path forward.
For a team so desperate for good news, Nov. 23 might be the most important day of their future — and the last chance to salvage what’s left of the Angel Reese era.
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