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If it weren’t for bad luck, the Chicago Sky wouldn’t have any luck.
Chicago has found new and painful ways to drown in misery. They drafted Angel Reese, which should’ve been the beginning of a new era. But with Chicago missing the playoffs over the last two years and Reese calling out the organization for the lack of support she has on the court, her future with the franchise and Chicago’s direction going forward are very much in question.
To make matters worse, all the losing they did in the 2025 season didn’t help their odds for the No. 1 pick in the 2026 WNBA Draft.
Chicago swapped rights with the Minnesota Lynx as part of the 2024 deal that allowed the Sky to draft Reese at No. 7 overall before then giving the Lynx sole ownership of their 2026 first rounder in order to select Hailey Van Lith at No. 11 in the 2025 draft. Thankfully, the Sky have the Connecticut Sun’s first-round pick, a byproduct of the 2924 midseason Marina Mabrey trade, and could still end up with the No. 1 selection in this year’s draft, with a 5.5 percent chance of winning the lottery on Sunday, Nov. 23 (6:30 p.m. ET, ESPN).
But would the No. 1 pick be enough to solve Chicago’s problems and keep Reese happy? Probably not. But with all the losses the Sky have piled up, they need a win wherever they can get it, and with one these prospects, some winning might become possible for Chicago:
With virtually all WNBA veterans being unrestricted free agents as a new CBA is being negotiated, let’s assume the Sky will need everything. Honestly, that might not even be an exaggeration.
The UCLA big is a top prospect and would bolster the Sky frontcourt. Could it work with Reese and Kamilla Cardoso? Will that be an overlap in talent? Perhaps. But again, if you can play a little, the Sky need you a lot, so if they earn the top pick, Betts has to be considered.
Olivia Miles is an elite guard. She spent four years lighting things up in Notre Dame and is now playing at TCU, hoping to finish her collegiate career with a bang. She’s averaging a career-high 17.5 points and 7.8 assists with the Horned Frogs, and many WNBA teams could use her services, the Sky included.
Regardless of whether Reese is on the Sky or not, Miles would be a superb addition to the team. If they have the opportunity to take her with the top pick, she might be the safest and surest bet Chicago can make.
If Flau’Jae Johnson reunited with Reese in Chicago, that might be too much flash and style to handle. It wouldn’t just be all style, though; Johnson has substance.
She is an electrifying perimeter player averaging 17.2 points, 4.8 rebounds and 3.8 assists per game. Adding her to this roster would be an enormous injection of talent, and on day one, she’d be a bona fide starter and a cornerstone of the franchise.
Things look bad for the Sky, but luck can change in an instant.
If they can fix things with Reese and win the draft Lottery, then they can begin to right this ship and start trending forward. If not, then a rebuild might be in order. For Chicago’s sake, let’s hope they either win the lottery or end up with a pick that allows them to still add a player that can help turn their fortunes around.
