For whatever reason, the 2026 WNBA free agency winds did not blow in Natasha Cloud’s favor.
But, one of the most high-profile unsigned free agents finally found a new WNBA home in the Windy City, as Cloud has a signed a one-year deal for $555,000 with the Chicago Sky.
General manager Jeff Pagliocca said of Cloud, “Natasha is one of the best passers and defenders in our league. She fits in with the other proven winners on our roster.”
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The decision to add Cloud at this late date, however, raises some questions about Chicago’s mostly-heralded offseason overhaul. A team that has too-often inspired scrutiny for their roster and asset management is again deserving of examination.
To make room for Cloud, the Sky waived Hailey Van Lith, the second-year guard who they drafted No. 11 overall in the 2025 WNBA Draft.
In the WNBA, an early-career waiver for a first-round pick is not out of the ordinary.
Yet, the Sky had invested extra resources in Van Lith. First, they traded for the No. 11 pick, extinguishing a pre-existing 2026 first-round pick swap with the Minnesota Lynx (which Chicago had sacrificed to Minnesota to trade up one spot for Angel Reese in the 2024 draft) and giving the Lynx sole control of the Sky’s 2026 first rounder, which was the No. 2 overall pick that became Olivia Miles.
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Chicago then sent second-round picks to both the Portland Fire and Toronto Tempo to prevent them from drafting a Sky player, quite possibly Van Lith (or Maddy Westbeld, who the Sky also waived on Monday).
Sure, those picks are likely to be players who will eventually be waived. Still, it was an unnecessary expenditure of resources.
Even more puzzling, a source indicated to ESPN that Chicago chose to cut Van Lith due to a “style-of-play preference,” something the organization seemingly should have been more cognizant of before now, as Tyler Marsh is in his second year as head coach and, even if Van Lith’s rookie season was interrupted by injury, he and his staff should have had a solid understanding of her fit.
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Per ESPN, Van Lith is expected to picked up by another team, with Kendra Andrews reporting that “active conversations are being held with a number of teams throughout the league.”
In addition to spotlighting the Van Lith mismanagement, the Sky’s decision to bring Cloud aboard sparks speculation about the status of Courtney Vandersloot. The Sky vet was slated to serve as the backup point guard behind free-agent addition Skylar Diggins once she fully recovered from the ACL tear that sidelined her for the majority of last season.
Does the signing of Cloud suggest Sloot will be out for longer than expected? If she was expected back soon, the Sky likely could have gotten by with Jacy Sheldon and Rachel Banham assuming primary ball-handling duties behind Diggins.
And if they 37-year-old Vandersloot is going to remain sidelined for awhile, something that would be reasonable since she is returning from a serious injury at and advanced basketball age, that then raises questions about Chicago’s decision to furnish her with a two-year deal for $750,000.
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Yes, it’s great to see a league legend finally get a big pay day before her time in the league is up. But, the realities of a hard salary-capped sport don’t allow for gestures of generosity, especially for a team trying to win now.
Whenever Sloot does return, it will be interesting if she is prioritized over Tash, even though Cloud is the better player. Cloud, certainly, is the superior defender. Offensively, Vandersloot has historically been a better shooter, albeit a much more hesitant one in her latter seasons. Cloud, while shakier and streakier, will fire away without fear, making her a more valuable piece in a Chicago offense that wants to create a more floor spacing.
It’s pretty clear that Cloud is going to help the Sky. She and Diggins will make sure the team stays lit with a competitive fire. She’s a great teammate and a fan favorite. And, she’s certainly capable of some big scoring games.
However, her late-breaking arrival, instead of being a moment of celebration, exposes the poor team-building process that continues to plague the organization.
