Skylar Diggins is ushering in a new era for the Chicago Sky, but questions remain after chaotic offseason

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Skylar Diggins is ushering in a new era for the Chicago Sky, but questions remain after chaotic offseason

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

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

When Candace Parker sprinted past Skylar Diggins in the final seconds of the 2021 WNBA Finals, it marked a defining moment for both players. Parker was celebrating the Chicago Sky's first championship in franchise history. Diggins, then with the Phoenix Mercury, was already untucking her jersey in defeat.

Nearly five years later, neither the Sky nor Diggins have won a playoff series since that night. Their new partnership aims to change that—and it couldn't come at a more critical time.

"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 last month. She emphasized the organization's determination to return to elite form after going 13-61 over the last two seasons and finishing tied for last place in 2025.

The Sky's offseason was nothing short of chaotic. They traded away rising star Angel Reese and made some head-scratching moves with draft picks. But for general manager Jeff Pagliocca, the vision is crystal clear: "We have high expectations. We have a group of people that won't accept anything but keeping championship standards here."

At the heart of that vision is Diggins—a seven-time All-Star and six-time All-WNBA honoree who remains one of the most dynamic guards of her generation. More than her stats, it's her fierce competitiveness that the Sky believe will transform their locker room culture.

"It's so important to have Skylar here," said guard Rachel Banham, one of only five returning players from last season's roster. Banham, who also played with Diggins on the Lunar Owls in Unrivaled, added: "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 went back to the drawing board. Countless discussions later, they forged a new identity for Sky basketball built on "toughness and grit." They targeted players who were "gonna fight at all times."

The 2026 season represents a fresh start for Chicago—a chance to write a new chapter after a difficult two-year stretch. With Diggins leading the charge and a roster built around resilience, the Sky are betting that their championship pedigree isn't just a memory, but a blueprint for what's to come.

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