Chicago Sky Open Post-Angel Reese Era With Win—But Questions Remain
The Chicago Sky picked up a win in their first game post Angel Reese trade, which is a solid start considering the team only won 10 games last season.
The Sky notched a 98-83 victory over the Portland Fire to start the 2026 WNBA season. Six Sky players ended the night in double figures, including veteran center Elizabeth Williams off the bench, while two finished the contest with double-doubles. Former Los Angeles Sparks guard Sarah Ashlee Barker scored 13 points as a reserve for the Fire as she worked off screens to score on more routine plays.
The Sky, who rolled out their fourth "new-look" roster in as many seasons during their matchup with the Fire, took at least one step closer to answering some of their most pressing questions for their 2026 run with their weekend win. A shorter rotation, which featured seven players earning about 15 minutes or more, gave plenty of time for new and familiar faces alike to show what they're capable of as five players were listed as out of the Sky's season-opening matchup. What will ultimately define what could be a pivotal point in Chicago's recent rebuild? And how close are the Sky to finding a much-needed direction after a handful of turbulent seasons?
Who Will Take Point for the Sky in the Post-Angel Reese Era?
If there's one thing the Sky love, it's constantly keeping their fans on their toes.
The revolving door of new Sky eras continued its inexorable turn as Chicago shipped Angel Reese to the Atlanta Dream just one week before the WNBA Draft was set to begin. Three picks and several offseason moves later, Chicago seemed set to begin yet another new chapter of its ever-changing history since it won its first-ever championship in 2021. Only five players on this year's opening night roster and developmental contracts suited up for the Sky at some point during their 2025 campaign, including a holdover of one of the final remnants of the James Wade era in Williams.
While a few Sky options had plenty of positive moments in their win over Portland, some expected leaders emerged to potentially take the mantle of face of the franchise following the departure of their young captain.
Guard Skylar Diggins, who signed a 2-year deal with the Sky a short while after the Reese trade, quickly emerged as a lead guard after ending the night with 21 points, 11 rebounds and seven assists. The 7-time All-Star showed out as a solo scorer and as a guard pairing with center Kamilla Cardoso, both of which the Sky were in desperate need of as they searched for a stable option at the one following the departure of Courtney Williams. Cardoso, now in her third year as the Sky's starting anchor, played to her own strengths as she racked up a team-leading 22 points and 14 boards. Forward Rickea Jackson used an all-around night to complement 19 points with seven rebounds and three assists.
Is the Sky's Young Foundation in Good Hands?
Whatever the Sky saw in the 2024 draft, it must have been nothing short of spectacular.
The Sky now sport the third, fourth and fifth-overall picks from the same draft that saw Reese fall into their range in the first round. All three players took up starting roles against the Fire, including guard Jacy Sheldon, who joined the Sky via an April trade with the Washington Mystics. Guard Carla Leite, who was selected two picks after the Sky took Reese, finished the night with 18 points and three assists for the Fire.
While the Sky again chose veteran talent over youth in this year's offseason, they still at least have a few young players to pair with their most recent influx of experienced options.
Guard Gabriela Jaquez, the No. 5 pick in this year's draft, earned 10 points, seven rebounds and two steals as she slotted into a starting spot on Saturday. The Sky signed forward Maddy Westbeld and guard Aicha Coulibaly to developmental contracts after the two were selected in the 2025 WNBA Draft. Coulibaly played in about six minutes during Saturday's showdown, where she logged two rebounds and one assist. Chicago restarted its trend of finding training camp talent with guard Sydney Taylor, a tradition highlighted by a few emerging players since the Wade era, who played in four minutes in the Sky's opener after dropping 23 points in Chicago's second preseason game.
Should Cardoso and Jackson continue to find their way in Chicago, the Sky can at least count on a few hands to hold up the weight of their future in their most recent era.
Are the Sky Finally Ready to Win Now?
It's a tale only slightly older than the Reese era itself for the Windy City squad: the Sky's top decision-makers choosing to follow a video-game-like retool defined by get-good-quick solutions over building a long-term foundation.
From Wade desperately dumping draft picks in a 2023 trade for guard Marina Mabrey before he skipped town in the middle of the season for an NBA assistant coaching job, to now-GM Jeff Pagliocca doubling down on a "win-now" mentality after the Sky earned their lowest winning percentage since their inaugural year in 2006 during his exit interview last season, the Sky have continued to push off real rebuilds to go all-in on immediate results. Despite their best efforts, Chicago has gone 42-83 in the regular season since it earned a franchise-high 26 wins in 2022. It somehow fell further than its 13-win run in 2024 while tying with the Dallas Wings for last place in the WNBA standings four months after Pagliocca first preached being in a "win-now mode" during his 2025 Media Day conference.
Could this year be the year they finally come close to turning it all around?
Kamilla Cardoso and Skylar Diggins become the first duo with 20-point double-doubles in a WNBA season-opener EVER 🙌 https://t.co/VHiAFaQNuR
— ESPN Insights (@ESPNInsights) May 10, 2026
The Sky took a few steps closer to finding their long-awaited winning ways with a victory on the road. Despite being outscored by 12 points in the third quarter, the Sky still battled their way up to a comfortable lead by the halftime horn and pushed away any hope of a comeback with a lopsided run in the fourth quarter. Cardoso and Diggins became the first duo with 20-point double-doubles in a WNBA season-opener, according to a Saturday tweet from ESPN Insights. The Sky outdueled their West Coast counterparts in the paint while flying ahead on the boards with 46 rebounds to Portland's 24. Chicago will have a few key tests before it returns to Wintrust Arena for the first time in its regular-season run, but it will at least be closer to putting it all together if its stars can continue to chime in sooner rather than later.
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Alex Sabri began contributing to Women's Fastbreak On SI in May 2026. He also covers Ohio and Detroit sports for On SI and the BIGPLAY Sports Network.The Purdue and Cleveland State graduate has over four years of journalism and sports media experience across collegiate and professional sports and local coverage.Though he specializes in covering professional hoops, his interests include the WNBA, NBA, NFL, Cleveland Guardians and college football and basketball.
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