1 pro, 1 con of the Chicago Sky going all in for Courtney Vandersloot

New York Liberty v Minnesota Lynx - Game Four
New York Liberty v Minnesota Lynx - Game Four | David Berding/GettyImages

A few of the WNBA's bigger names have changed teams as the league's free agency period gets into full swing.

Center Brittney Griner, a long-time member of the Phoenix Mercury, shocked the WNBA world when she announced she would be signing with the Atlanta Dream on Tuesday. The news broke just hours after forward Alyssa Thomas was shipped over to the Mercury from the Connecticut Sun. Lincolnwood's own Jewell Loyd was sent off to the Las Vegas Aces while guard Kelsey Plum was sent to Los Angeles.

How concerned should the Chicago Sky be in joining the league's arms race before what could be a pivotal year in its history?

Chicago Sun-Times Sky reporter Annie Costabile wrote the Sky met with guard Courtney Vandersloot in Miami in a Tuesday article. Vandersloot, a 7-time assist champion and 5-time All-Star, won a championship with the New York Liberty two seasons after signing with the squad.

"Sky general manager Jeff Pagliocca and new coach Tyler Marsh met with unrestricted free agent Courtney Vandersloot and restricted free agent DiJonai Carrington last week in Miami," the article read. "Since then, the only free-agent news surrounding the Sky is that Pagliocca has been in talks with several general managers about possibly dealing the No. 3 overall draft pick, multiple league sources told the Sun-Times."

The Sky have the cap space to add the former Gonzaga guard. Chicago has the 3rd-most in the WNBA and just two players with a cap hit of $100,000 or more in 2025. Even if they choose to bring back every one of their restricted or reserved free agents, Chicago would still have a little room left for the 35-year-old guard should they sign both of their 1st-round selections.

The question is, should they go all-in for Vandersloot? Or should they try signing her for the right price without affecting their long-term future?

Pro: Bringing a known passer and Sky legend home

Vandersloot cemented her place in the Sky's history from the moment she joined Chicago in the 2011 WNBA Draft.

The Gonzaga sensation earned four All-Star selections, including one in her rookie year, with Chicago as she paved the path to becoming one of the best point guards in the Sky's short history. She is, by far, the Sky's assists leader with just under 2,400. The next leader, a 3-time All-Star and Vandersloot's wife in guard Allie Quigley, logged just over 680 assists with Chicago.

It's no secret the Sky are in need of a talented floor general in the absence of Vandersloot and guard Courtney Williams. Chicago did not have a player in the top-5 in assists per game for the first time since 2012 last season, with Vandersloot bobbing in and out of the 1st-place spot for a full decade. Having Vandersloot's passing, leadership and experience could be a major boost for a team looking for a new direction under a new head coach and two high-level young bigs from the 2024 draft.

Con: The potential long-term price

Bringing back a Sky legend and someone who answers one of their biggest questions in the short-term is a great choice, but only for the right price.

Should it be more than a larger short-term contract, it may be one that can affect the Sky's long-term future if they don't play their cards right.

"The Sky’s only hope of landing a player such as Vandersloot is if Pagliocca can move the team’s lottery pick to get an experienced shooting guard or two-way wing," Costabile wrote.

The Sky may be in a better position in the recent future after a pair of league-changing trades from the past week. Chicago has the right to swap 1st-round selections with the Sun, who just traded away one of their best players in Thomas, in the 2026 WNBA Draft. They can swap the Phoenix pick they acquired from last year's Kahleah Copper trade. Connecticut hired a new head coach in Rachid Meziane after Stephanie White, who saw two semi-finals appearances with the Sun, was hired by the Indiana Fever in November.

Still, it won't be a guarantee either one of those picks will hold the same value as their No. 3 pick this year.

With the biggest names out of contention for the Sky, and with a limited selection of who they can bring in with the No. 3 pick, it may hurt Chicago's long-term future to pull the trigger on a short-term option for what is only a chance at bringing in Vandersloot and attracting bigger-name free agents in 2026. And, in a draft with a talented guard class, it would be shortsighted to not at least consider who the Sky could take at No. 3.

Adding someone like Vandersloot isn't the Sky's only option to be competitive in the future.

Chicago could try to roll the dice on the draft and hope Notre Dame guard Olivia Miles falls to them in the lottery. Even if she doesn't, Miles's teammate in guard Sonia Citron can be a solid pick and a decent long-term option at the two. Guards like Maryland's Shyanne Sellers could be an interesting option to look out for if they strike out on Miles or want to trade down. The Sky could also try their hand at signing short-term options in free agency to temporarily add experience at the one while their younger guard options learn and grow in Chicago. Either way, the Sky must be patient in their rebuild and not mortgage the future for a chance at potentially landing bigger names next year.