Skylar Diggins is ushering in a new era for the Chicago Sky, but questions remain after chaotic offseason
The Sky traded away Angel Reese and were loose with draft picks, but there are reasons for optimism in 2026
In the closing seconds of the 2021 WNBA Finals, as Candace Parker sprinted the length of the court to start celebrating the Chicago Sky's first championship in franchise history, she ran right past Skylar Diggins, then a member of the Phoenix Mercury, who was already untucking her jersey in dismay.
Since that day nearly five years ago, neither the Sky nor Diggins have won a playoff series. They hope their newfound partnership will change that.
"I've been on the other side in 2021, playing versus that championship team, and just seeing the arena light up, seeing Chicago basketball at its peak," Diggins said at the Sky's media day late last month, when asked why she signed in free agency. She also pointed to the organization being "serious about wanting to get back to a high level" after going 13-61 over the last two seasons and finishing tied for last place in 2025.
"We have high expectations. We have a group of people that won't accept anything but keeping championship standards here," Sky general manager Jeff Pagliocca said. "We want to compete with and beat the best teams in the league, and we expect that out of the players every single day."
That starts with Diggins, the seven-time All-Star and six-time All-WNBA honoree, who was the headline addition during the Sky's busy, and, at times, confounding offseason. In addition to being one of the best guards of her generation, Diggins is a fierce competitor who will set the standard both on the court and in the locker room.
"It's so important to have Skylar here," said Rachel Banham, who is one of only five returners for the Sky (including developmental players), and also played with Diggins on the Lunar Owls in Unrivaled. "You guys know her intensity and competitiveness, it's just so important to this locker room. It's something that we need and it's something that she's gonna bring every single night."
After suffering through one of the worst seasons in franchise history last summer, Pagliocca and coach Tyler Marsh met to discuss their path forward. Over countless discussions, they put forth a new vision for Sky basketball based on "toughness and grit," and players they knew were "gonna fight at all times," Pagliocca said. "We wanted to make sure that the team was much more competitive than it has been."
It will be, but the path there deserves closer inspection.
A series of trades, good and bad
Expansion draft protection
On April 1, just before the historic double expansion draft, the Sky made deals with the Portland Fire and Toronto Tempo to ensure that neither club picked a player from their unprotected list. They gave the Fire the No. 17 pick (Frieda Bühner) in the 2026 WNBA Draft in exchange for the No. 21 pick (Latasha Lattimore) and sent the Tempo the No. 26 pick (Saffron Shiels).
Were those deals the end of the world? No, but making them was another example of poor asset management from a front office that has been notorious for playing fast and loose with draft picks.
The end of the Reese era
On April 6, the opening day of free agency, the Sky traded All-Star forward Angel Reese and a 2028 second-round pick swap to the Atlanta Dream for their 2027 and 2028 first-round picks. The relationship between Reese and the organization soured last season after she gave a controversial interview to the Chicago Tribune, and it ultimately wasn't a surprise that they parted ways in the offseason.
However, the return for a player of Reese's caliber was poor. The Dream won 30 games last season, have their entire core locked in for the next two years and should only be better with Reese. The picks the Sky will receive will almost certainly be late firsts, which are less valuable than ever now due to the new CBA and expansion. There's a real chance that trading Reese ends up being a salary dump.
More draft capital out the door
On April 11, the Sky traded their 2028 first-round pick to the Washington Mystics for Jacy Sheldon, who was the No. 5 overall pick in 2024. While Sheldon still has some potential as a defensive-minded guard who can space the floor, the Sky will be her fourth team in three seasons. Punting on your first-round pick in the Sarah Strong draft class for a player who won't even be a starter is incomprehensible, especially when you don't yet know how the new roster will work together. The reward is just not worth the risk, and the Sky, more than any other franchise, should know the danger of giving up picks years down the line.
"We always make sure that we keep a healthy amount of them available as well," Pagliocca said when asked about his willingness to trade draft picks. "We know that we need to keep them to use in the draft, we know that we need to keep them to use to make moves. We're gonna stay aggressive, we're gonna make sure we're making informed decisions."
"This one with Jacy Sheldon, she's a player that we see here for the long term," he continued. "She's a player under team control for the next couple years, she fits exactly who we are and who we want to be. These are conversations that Tyler and I have, but we will make moves if we think that there's a player that's gonna fit with who we're trying to be."
3-4-5
On April 12, the Sky traded veteran guard Ariel Atkins – acquired last offseason from the Mystics in exchange for the No. 3 in the 2025 draft (Sonia Citron) and a 2027 first-round swap – to the Los Angeles Sparks for former lottery pick Rickea Jackson. While there were real questions about their first three trades of the offseason, this one was a clear win for the Sky. Atkins is a very solid player, but Jackson is nearly five years younger, has a higher ceiling and fits a positional need after the Reese deal.
The Sky drafted Kamilla Cardoso at No. 3 in the 2024 draft, and after acquiring Jackson (No. 4) and Sheldon (No. 5) this offseason, they now have the Nos. 3-5 picks in that class.
High marks in free agency
Historically, the Sky have not been a free agent destination, but that changed this offseason thanks to Pagliocca's efforts, a wide open cap sheet and the team's new practice facility, which is set to open later this year.
In addition to Diggins, one of the best free agent signings in franchise history, the Sky signed Azurá Stevens, Natasha Cloud and DiJonai Carrington, and re-signed Banham, Courtney Vandersloot and Elizabeth Williams.
"We knew that earning the respect of a Skylar, of an Azurá, retaining players that were here, was gonna take some real sincerity, and a genuine plan from our end of who we wanted to be," Pagliocca said. "I think they listened... Looking at our roster now, you see more of an athletic group, shot-creative group, some more size, more versatility than we've had over the last couple seasons."
Diggins, Cloud, Carrington (and Sheldon) is an incredibly aggressive and defensive-minded perimeter group that will never have its toughness questioned. Stevens, who was a member of the 2021 title team and has familiarity with the organization, is one of the best 3-point shooting bigs in the league and will help space the floor around Kamilla Cardoso.
The only downside in the free agency department is that neither Carrington (foot), Stevens (knee) nor Vandersloot (knee) will be ready for the start of the season. Additionally, Cloud may take some extra time to get fully up to speed because she didn't sign until May 4 and missed the majority of camp.
A draft-day reach?
The Sky won the No. 2 pick in the lottery, but owed their first-round pick to the Minnesota Lynx via the trade to acquire the draft pick that became Angel Reese. They still wound up with the No. 5 pick, however, because they controlled the Connecticut Sun's first-round selection via the Marina Mabrey deal.
To everyone's surprise, they selected Gabriela Jaquez with the fifth pick. While Jaquez established herself as a surefire first-round pick after a strong senior season at UCLA, which she capped with a historic performance in the Bruins' national championship game victory, no one expected her to go in the lottery.
Jaquez's brother, Miami Heat forward Jaime Jaquez Jr., told CBS Sports earlier this year that his sister would be an "instant plug-and-play" wing due to her versatility and motor. But as great as Jaquez is at coming up with loose balls and grabbing key rebounds, those are role player traits. You would hope to get more than a role player in the lottery, and Jaquez doesn't have a ton of upside because she hardly creates any of her own offense.
There's a good chance Jaquez winds up being a solid WNBA player, but it felt like the Sky prioritized finding someone who would fit their culture over talent – an honorable path, but not necessarily the most successful one.
Better, but to what end?
Pagliocca, the Sky's former director of skill development, was hired as the team's GM in October of 2023. In two-plus years in charge, he's done a significant amount of wheeling and dealing, but very little winning. The Sky are 13-61 in his two seasons, have not finished better than 10th place and have not been better than 10th in net rating.
His busiest offseason yet was a courageous attempt to change the team's fortunes. He is desperate to build a winner, and you have to respect his earnestness and self belief even if you disagree with his shortsighted moves – and many people do. In particular, there have been numerous complaints about his carefree nature when it comes to draft picks, which has already hurt the team's present (again, they could have Sonia Citron right now) and may severely impact their future.
"We trust who we are," Pagliocca said. "We trust our staff, we trust our ownership and we trust the core that's been here and has stuck around. We understand that we needed to get better. We have high aspirations and high expectations. We know who we are, we know who we're trying to be and we'll have to wait and see, but we have a lot of players here who I don't think are going to accept failure this time around."
This is the most talented roster he's put together in Chicago, and the Sky are going to be much better than last season. But to what end? To simply get into the postseason so they can say they're a playoff team and likely avoid having to swap first-round picks with the Mystics next year? Or to actually compete?
'She's got a lot left in the tank'
The answer to those questions ultimately circles back around to Diggins.
"It's been two weeks and I can't put into words the magnitude of what her presence has been thus far," Marsh said. "You feel it as soon as she walks into the gym. There's an accountability, there's a level of focus that she demands that's contagious to the rest of that group. I think they feed off of that. That's what we wanted when we brought her in."
Her teammates concurred. Stevens called her the "ultimate competitor," and added that "having somebody with that type of toughness just elevates everybody around her" because it "forces everybody to get in line or get out of the way." Sheldon, who grew up watching Diggins, is thrilled to be playing with her instead of against her now, and said she's been trying to "absorb anything she has to give. She's a great teammate, that's someone you want on your team."
Diggins' leadership and locker room presence are already paying dividends, but intangibles only matter so much. They need her to produce at a high level on the floor, and while she showed last season she can still do so, she's been in the league for more than a decade and will turn 36 in August. How far can a Diggins-led team go in 2026?
The Sky hope it's further than they've been in years.
"She's got a lot left in the tank," Marsh said. "And we're gonna try to push her to the max with that."
