Grading the Cloud-Van Lith Move for the Chicago Sky

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The Chicago Sky enter 2026 with a completely new roster on board. After taking All-Star forward Angel Reese off of the team in a trade with the Atlanta Dream. The team was not done. The team purged nearly their entire roster.

Players like Sidney Cooks, Courtney Harris, Maddy Westbeld were dismissed. But one of the biggest departures happened on May 4, 2026 when the Sky waived their 2025 first round draft pick Hailey Van Lith. In her place was guard Natasha Cloud.

But was this move smart or dumb?

The Move: Signing Natasha Cloud

The Chicago Sky signed Cloud to a one-year, $555,000 deal. This move was an excellent one by the Sky. Due to numerous efforts of failing rebuilds, the team added one of the most elite perimeter defenders in the WNBA. She also is a tremendous floor general.

Due to her ability to set a culture, she provides veteran stability that the Sky did not have in 2025. She averaged 10.1 points and 5.1 assists in 2025 with the New York Liberty. The backcourt is going to be a problem for defenses. Chicago general manager Jeff Pagliocca had this to say to ESPN:

“Natasha is one of the best passers and defenders in our league. She fits in with the other proven winners on our roster.”

She now joins All-Star guard Skylar Diggins-Smith, who is also a great defender and floor spacer. Opposing guards will have issues handling them on both ends of the floor.

The issue however, is that since she was signed for a one-year deal, it will be an expensive rental if Chicago does not make the postseason.

Grade: A-

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The Waiving of Hailey Van Lith

Another polarizing move that the Sky did was waive Hailey Van Lith. In pursuit of a title, the move would make sense. However, Chicago is not in position to make a title run. So it is a tough look for a management crew to cut a first round pick after just 29 games.

Time will tell if this move was the right one. But given her history already, the move may not be as bad as it looks. Once considered one of the more recognizable names in college basketball, she hit a speed bump the minute she got into the WNBA. Sky head coach Tyler Marsh had this to say on to the Chicago-Sun Times:

“Sometimes it comes down to a numbers game. It’s not necessarily anything that Hailey did or didn’t do. She works hard. She battled through injuries throughout this last year. She competes, she’s coachable, she’s great in the locker room. There’s a bright future for her in this league.”

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Van Lith struggled to find her rhythm as a pro. She averaged 3.5 points in 2025 and spent most of her rookie year on the sidelines or playing in the last few minutes of a contest.

The coaching staff cited a ‘style of play preference’, signaling they prefer Cloud’s defensive-first, pass-heavy approach over Van Lith’s score-first mentality.

She is still young and full of potential. It can be only a matter of time before a team can pick her up. She can still turn her career around. But she is going to be going back to square one. She is a good shooter and can give a team an offensive boost.

By cleaning the spot, the Sky can fit in Cloud’s massive salary under the cap. However, Van Lith showed flashes of her potential in the 2026 WNBA preseason by averaging 12.6 points. By waiving her, the Sky loses a young, high-upside asset for nothing.

Grade: C+

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Conclusion

However, if the Sky can capitalize on this move and can get the best out of Cloud, then the move that the Sky made was worth it.

Thanks for reading!