The Chicago Sky’s season tips off on May 9 against the Portland Fire, and the city is currently navigating a complicated kind of grief.
Ever since the Sky clinched their sole championship title in 2021, the team has taken hit after hit. Between delayed plans for the new practice facility ahead of the WNBA All-Star Game in Chicago this July, the recent Angel Reese trade to the Atlanta Dream for a haul of draft picks and a new roster full of former rivals, can things get better for the franchise voted “worst-run” in an anonymous league-wide poll less than a year ago?
According to Skytown, the affectionate nickname for the fanbase and staff, only time will tell.
It is clear the city that birthed the league’s first independently-owned franchise wants a winning basketball team. This season, the Sky is fighting to emerge from a turbulent two-year slump, where the victory column failed to hit 15 in either season. (The WNBA plays 44 regular season games from May to September, by the way).
“I’m expecting a competitive basketball team,” longtime season ticket holder (a.k.a. Skyrider) Matthew Moore told The TRiiBE. He interned with the Sky’s creative and marketing operations department in 2014 when the team was led by Elena Delle Donne, Sylvia Fowles and Courtney Vandersloot.
“[As a fan], I am sad about the loss of Reese,” Moore continued. “We’re early on, so there’s excitement about where this team could go, and I think Chicago should be excited with this current roster of players from a perspective and personality standpoint.”
The Sky must forego the days of “give Angel the ball and pray.” Sky general manager Jeff Pagliocca and head coach Tyler Marsh have put together what is arguably the most successful-looking roster on paper since 2023, filling critical gaps with the signings of proven playmaker Skylar Diggins, defensive specialists Rickea Jackson and DiJonai Carrington, and three-time All-Star veteran guard Natasha Cloud. Azurá Stevens has also returned on a historic three-year, $3.15 million contract.
Fans are anticipating an energized era of progress via the league’s new Collective Bargaining Agreement (CBA). But on the court, success translates into a sophisticated blend of veteran grit and the young dynamism of Jackson and center Kamilla Cardoso — despite their collegiate rivalry.
Between the high-stakes trade of a cultural icon and the city’s bid to host the league’s big stage in just a few months, we’re taking a look at four pressure points shaping the state of the Sky this season.
Grieving the Angel Reese trade
Reese will be missed in Chicago. Much like the arrival of QB Caleb Williams, the Bear’s No. 1 draft pick in 2024, Reese — also drafted in 2024 — brought a celebrity allure to Chicago that forced the city and sports world to pay attention. She offered locals an unapologetic main character energy the team had not seen since its championship victory in 2021.
“I feel like we drafted someone that embodied the vibes of Chicago,” Chicago sports fan Antoine Brown said. He’s also a Louisiana State University alumni like Reese, affectionately known by fans as the “Bayou Barbie.”
“Angel was hardworking,” Brown continued, “Even when it wasn’t always pretty, which was such a Chicago fit.”
But that fit came with a price. Skyrider Eva Terry said the price of her season ticket package increased by 40% when Reese came to Chicago, which was also the first time she had seen the team cater to one player.
“They told me part of my money was going to funding for the new practice facility,” Terry said. “As a season ticket holder, when you invest, you want to see a return. But we barely had wins, so it just became about seeing this one special player.”
Terry explained what she called “the Angel Reese effect,” and the positive impact it had on Skytown culture during a losing season. “It brought more women and little girls to the game than ever before. That was the Angel Reese effect here in Chicago,” she said.
Both Terry and Brown said it is likely many fans shifted their allegiance to the Dream, following Reese’s move to Atlanta. However, they said, the culture will remain in Chicago if the team commits to winning.
“If we’re winning with the stars we have now, a Black fanbase will likely show up,” Brown said. “But it won’t ever be as big as it was for Angel, even though we also weren’t winning much.”
For Chicago sports culture at large, the Reese trade felt familiar. Fans drew painful comparisons to when the Chicago Bulls traded homegrown MVP Derrick Rose to the New York Knicks in 2016.
“You got eight years with Rose in Chicago, but we didn’t get that with Angel,” longtime Sky fan Kenneth Anthony said. “I don’t think there’s ever been a Sky player besides her who connected as deeply with the city and die-hard fans here in the same way Rose resonated.”
The Skylar standard
Now, Olympic gold medalist Diggins is the face of a new era of Chicago basketball. She led the Phoenix Mercury to the WNBA Finals in 2021, but lost to the Candace Parker-led Sky.
“Everywhere Skylar went, she won,” Brown said. “Even if those wins did not result in championships, the teams she’s been on have been successful. Players on our roster are likely asking, ‘How do I become a winner? What can I do to impact winning?’ and Skylar is the one person that can steer them in the right direction.”
The 13-year WNBA veteran has been known to have a tumultuous relationship with the Phoenix Mercury, issuing a level of public accountability that does not spare the front office. In 2023, for example, she publicly called out the organization for not letting her access the team’s resources while on maternity leave.
And while the Chicago Sky anticipates the South Bend, Indiana native to be the head chef of a winning recipe fans have been craving, Pagliocca understands the front office’s responsibility to embrace Diggins’ court authority as a catalyst for collective growth. In a preseason press conference, he said he wants to build a team that works to avoid criticism from Diggins.
“I don’t want to deal with Skylar Diggins every night if she doesn’t have players she can go to war with, so we made sure she understood the vision,” Pagliocca told reporters.
Views from the stands
But Diggins isn’t the only one keeping an eye on her Chicago Sky experience. The rest of Skytown is conducting their own audit.
“In our first preseason game against the Mercury, we looked more defensively engaged than last year,” Brown said about the Sky’s progress. “I was like, ‘OK, Jeff is putting the team together for Tyler’s vision and I can give it some time to develop.”
A consistent concern across most of the fanbase is that the front office doesn’t know how to best engage with its Sky community. Some examples include playing a poorly-timed tribute video for Reese during the April 29 preseason game against the Dream only weeks after the trade, or gifting Skyriders with socks and T-shirts that do not fit diverse body types.
Skyriders like Terry are especially leery of Marsh’s leadership ahead of his second full season as the Sky’s head coach, noting the grace period in Chicago sports is “notoriously short.”
“Some of these people have had two years to learn how to course correct,” Terry said. “If they want to keep the jobs they have, they should be held accountable for mistakes or take it elsewhere.”
But other fans like Aerie Van Meter, a Skyrider since 2018, are choosing a third path: low expectations and high enjoyment.
“We aren’t necessarily rebuilding,” Van Meter said. “We’re not contenders, we’re not a playoff team, we’re not a dark horse, we’re just out here, and sometimes there’s nothing wrong with that. We’re just playing basketball and it’s fun.”
Chicago’s WNBA All-Star summer 2.0
The 2026 WNBA All-Star Game will be played in Chicago on July 25. Events will be split between Wintrust Arena and the United Center, marking the second time in four years the WNBA festivities will be held in the city.
“The bar was set high last year in Indianapolis,” said Anthony, who, in his free time, writes post-game analysis about Sky games in Facebook groups. “As a competitive city, we want to outshine it. There’s a million more things to do in Chicago than in Indianapolis, so this is a marquee opportunity to show that independent ownership groups can still be competitive culturally and resource-wise.”
Anthony pointed to the 1988 NBA All-Star Game Chicago hosted as a blueprint, where Bulls star guard Michael Jordan was named both MVP as well as dunk contest champion over Dominique Wilkins. Jordan famously credited that 147-point win — a performance cemented by an iconic flight of power from the free-throw line that earned a perfect score of 50 — to the home-court advantage, proving that when the city shows up, victories are sure to follow.
“Everything [that] the Bulls franchise means to Chicago and its fans today took off in alignment with that event,” Anthony said. “We should treat hosting this All-Star game like that, or [the way] L.A. will treat the Olympics, or [the way] Atlanta will treat the World Cup.”
