The Sky don’t have an All-Star in 2026, but plenty of players they could have drafted or failed to keep will be in Chicago for the game.
So here’s a rundown of their biggest All-Star whiffs, ranked not by the caliber of the player, but by what each case reveals about the Sky.
Olivia Miles is the most recent and tantalizing, though not entirely their fault. Angel Reese represents the costliest breakdown. And Marina Mabrey is the OG example of what keeps going wrong for the Sky.
3. Olivia Miles
The No. 2 pick in the 2026 draft used to select Miles would have belonged to the Sky. It’s the pick they gave up in 2024 to snag, then fumble, Angel Reese.
Miles is having an MVP-caliber rookie season, and the Minnesota Star Tribune has deemed her the state’s most likable athlete since Kirby Puckett. In Chicago, she could have been the most likable athlete since someone people have actually heard of.
Like Michael Jordan.
So why isn’t Miles the No. 1 whiff?
Mostly because bad luck played a major role. Had Miles entered the draft in 2025, which she strongly considered, or had the Wings done what everyone now agrees they should have done in 2026 and taken Miles over Azzi Fudd, she wouldn’t be linked to the Sky.
“You have to get lucky,” Lynx head of basketball operations Cheryl Reeve admitted when discussing Miles ending up in Minnesota. “Lottery balls have to go your way.”
Beside the aw-shucks modesty from Reeve was also a bit of a flex.
“Obviously, at the 2024 draft, we wanted to take a swing at a lottery pick in 2026,” she said. “That’s what you do when you’re trying to project teams. We have people who get paid to project for us.”
Catch the subtle reminder that the Lynx have invested in number-crunching and forecasting in a way the Sky, and many other teams, have not?
Still, some credit to the Sky for identifying Reese’s potential. They saw past the conventional wisdom that her game wouldn’t translate to the pros. If Reese were playing in her third All-Star Game for the Sky, Miles would be a road not taken, not a whiff.
2. Angel Reese
The Sky and Reese mutually decided to part ways this offseason, leading to her trade to Atlanta.
In a vacuum, sending away one of the game’s most recognizable young stars and the league’s best rebounder for what will likely be low first-round picks will always look pretty ugly.
But there’s a world in which the surrounding moves validate the new direction. Rickea Jackson might have the talent and personality to become the face of the franchise once her ACL heals. Adding Azurá Stevens’ floor spacing has been successful. Undrafted rookie Sydney Taylor is also showing the potential to be a star.
The problem is that none of it has showed up in the Sky’s record.
And in trading up for Reese, the Sky essentially leveraged their own lack of foresight. They sacrificed a pick in a loaded 2026 draft for a star they knew would be a handful, then showed little savvy in actually managing the relationship.
They fired Teresa Weatherspoon, the coach Reese called the reason she was in Chicago. They failed to move the team out of the suburban park district during her tenure. They did not provide the resources or continuity necessary to make such a major investment last.
Not to let Reese totally off the hook. Her public criticism of the roster genuinely did not fly with her teammates, and her talents were not enough to make them a winning team.
But her assessment of the organization was true, and her willingness to say it was not out of character. The Sky got what they paid for.
They sold their Olivia Miles lottery ticket to bet on a star who calls it like she sees it, and it went about as well as the Lynx projected.
1. Marina Mabrey
Mabrey is the original example of the Sky’s intertwining problems since the core of their 2021 championship team broke up.
They can identify and acquire talent, often by making bets on players who have not always stuck elsewhere. They just fail to build a strong enough structure around them to make Chicago different.
After a brief stint with the Sun, Mabrey has proved herself in Toronto to be the bucket former Sky coach and general manager James Wade envisioned. She tied the all-time single-game scoring record with 53 points and is shooting 39.2% from deep on 8.4 attempts per game.
Wade sacrificed a pile of draft capital to bring her in, confident he could nurture her into an All-Star. Then he left midway through the 2023 season, and Mabrey asked out midway through 2024.
She wanted to keep her full reasoning “in house,” but acknowledged that she had been brought to Chicago to play in Wade’s system, not Weatherspoon’s.
That is the trouble with changing coaches, systems and organizational direction so frequently. A player acquired for one vision can quickly find herself stranded in another.
The part that stings is that the trade itself could have worked. None of the draft capital surrendered for Mabrey amounted to anyone special, while Mabrey became an All-Star.
Which is to say: The Sky’s aggressive approach could be vindicated if they could actually retain stars.
Instead, Mabrey — like so many others — blossomed elsewhere.
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