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Skylar Diggins-Smith and Jeff Pagliocca (Image via: Imagn and @jeffpagliocca on IG)

Imago
Skylar Diggins-Smith and Jeff Pagliocca (Image via: Imagn and @jeffpagliocca on IG)
Chicago’s bid to rebuild hinges on Skylar Diggins-Smith, and the team’s GM is already managing expectations before she even steps on the court. It’s quite certain that the Diggins-Smith signing is a bid by the Chicago front office to replace Angel Reese, who departed a couple of weeks back. Now, bringing an established player onto the team amid such a situation will, of course, raise expectations around her, and the Sky general manager recently touched upon that.
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Speaking at the team’s introductory press conference, featuring all the Chicago Sky’s new acquisitions, Sky GM Jeff Pagliocca remarked that it’s the team’s responsibility to provide a veteran like Diggins-Smith with the tools to succeed on the court. And also make her feel assured in the franchise, and not just throw the dice on her to rebuild the team alone.
“I think when you get into a conversation with Azura Stevens or Skylar Diggins-Smith, players that we were initially able to engage with, they need to feel confident that we’re going to build a team around them,” Pagliocca said. “I don’t want to deal with Skylar-Diggins every night if she doesn’t have players that she can go to war with, right? So, we made sure that she understood the vision and that stuff should matter to everybody.”
“We got some smart people who have weighed in here. But both Tyler (Marsh) and I had a plan, and we’re really just proud that we wanted to come here and go to war with us,” Pagliocca said.
Coming off two losing seasons, the Chicago Sky have placed a clear bet on Diggins-Smith in this rebuilding phase. There’s no doubt about her stature and her skill set as a pro player (averaging 16.4 ppg across her career). But the issue lies in Diggins-Smith’s age. The Sky let their franchise star, Angel Reese, go, who was supposed to be the flagbearer of the team for years to come.
And they replaced her with a 35-year-old Diggins-Smith, which is already a questionable move and shifts the pressure on the Chicago Sky. Yet despite all these, Pagliocca has made it clear that the team is focusing on the “win-now” mentality with players like Diggins-Smith and Stevens.
“We’re gonna remain in ‘win now mode’ as long as I’m here. I think this week showed we’re gonna stick to a plan,” he said. “I don’t think making the playoffs should ever be a goal moving forward. We want to compete … what ‘winning now’ means is getting ultra competitive players here who won’t live with anything less than success.”
Now, it’s very important to understand that when a player like Skylar Diggins-Smith joins a franchise, the pressure also falls on that franchise to provide a support system for the player to thrive and the team to succeed. Arriving from the Seattle Storm, where she played alongside veteran Nneka Ogwumike, she won’t have a similar spectrum in the Sky.

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Jan 17, 2025; Miami, FL, USA; Skylar Diggins-Smith (4) of the Lunar Owls drives toward the basket as Breanna Stewart (30) of the Mist defends during the first half of the Unrivaled women’s professional 3v3 basketball league at Wayfair Arena. Mandatory Credit: Jim Rassol-Imagn Images
With the Sky, she will have some experience with Elizabeth Williams and Azura Stevens. But on the court, it will be Diggins-Smith who has to call most of the shots. Speaking at the introductory press conference, the 7-time WNBA All-Star made it clear that she will push her teammates around her, as she has throughout her pro career.
“Everybody that knows me knows I challenge my teammates around me,” Diggins-Smith said. “I wouldn’t say I’m an easy teammate, but I’m a good teammate because I’m going to challenge you.”
The Chicago Sky are quite substantial on paper to support Skylar Diggins-Smith, especially after they made a few more notable offseason acquisitions. In the free agency window, they got Rachel Banham and Elizabeth Williams, two experienced campaigners. In the WNBA draft, too, the Sky selected rising young talent Gabriela Jaquez in the first round. They followed it up by acquiring Latasha Lattimore and Tonie Morgan in the latter stages.
But up next, it will be upon these players to build that winning mentality on the same lines as their veteran, Diggins-Smith. It’s even more important for these players, given that the former Seattle guard is coming to Chicago with some high aspirations.
Skylar Diggins-Smith Confirms the Chicago Sky Isn’t Her ‘End’ Plan
Diggins-Smith’s move to the Chicago Sky can be touted as one that very few could have expected. Of course, she was a free agent, so her signing didn’t create any complications for either her or the Sky. Even then, a veteran like her joining a team that hasn’t just qualified for the playoffs in the last two seasons but has also won just 30% of its games is slated to raise a few eyebrows.
Many would have thought that with Diggins-Smith approaching the last stretches of her career, the Sky might be one last dance for her. But, as reality set in, she has completely thrown such perspectives out the window, making it clear that she wants to compete and win with the team.
“I’m bought into the vision,” Diggins said. “I’m not just coming here saying this is the end or whatever for me. I want to play some good basketball. I still have a lot to go as far as what I feel like I can do, especially with this team.”
The roster is set, and the belief is already there. Now, it’s just the waiting game till the official season begins for the Chicago Sky. The Sky will play their first official game on May 9 against the Portland Fire.
But before that, they have a training camp, which will begin around April 19. Furthermore, they have during a couple of preseason games against the Phoenix Mercury and the Atlanta team, which we can see Diggins-Smith don the Sky jersey for the first time.
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Snigdhaa Jaiswal