Mapping out the Chicago Sky’s difficult free agency decisions

The case for and against re-signing each of the Chicago Sky’s seven players entering free agency this offseason

The Chicago Sky find themselves in a much different predicament than last season this free agency.

Expectations were measured entering last season. Chicago had an unproven rookie head coach and a 25-43 record the previous two seasons. A good mix of reliable veterans and young talent was a recipe for either internal growth or another year of turbulent play.

But this year things are clear, or at least clearer than last year: title contention or bust. Head coach and general manager James Wade has been consistent in his approach that returning last year’s core is the franchise’s best bet at a title run in 2020, relying on internal growth and chemistry to push them past last year’s second round finish.

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That goal, however, seems impossible with the WNBA’s new collective-bargaining agreement which increased the salary cap significantly, but raised maximum salaries out of proportion with the new cap. Kayla Alexander, Kahleah Copper, Stefanie Dolson, Jamierra Faulkner, Astou Ndour, Allie Quigley and Courtney Vandersloot all hit free agency this year, and Wade will have a difficult time holding all member of his core together.

The 2020 offseason has a bit of a wild west feel to it: while obvious max-level players and end-of-the-bench level players should be easy to dole out contracts to, what do you do with everybody in between? The market under the new salary cap is completely untested. Teams could start free agency with their money firmly in their wallets or there could be splashy offers early on. How many players the Sky can retain could easily come down to just tens of thousands of dollars.

Wade who will also have to navigate future salary cap in his decision. Both Jantel Lavender and Cheyenne Parker enter free agency next year, with Diamond DeShields and Gabby Williams becoming free agents the year after that.

Keeping that uncertainty in mind, here is the case for and against re-signing each of the Sky’s free agents.

Allie Quigley and Courtney Vandersloot

Barring a disastrous series of events, unrestricted free agents Allie Quigley and Courtney Vandersloot will be back with the Sky next season. The married couple own real estate in Chicago and Vandersloot has publicly expressed a desire to return to the Sky this season.

There is no case against re-signing both players. None. The only real uncertainty surrounding the duo will be what type of contract each player gets this offseason. But nobody will bat an eye if both players enter the season under multi-year max contracts.

Both Quigley and Vandersloot have been cored once—the core tag gives an automatic maximum salary for players and it gives teams exclusive rights to that player for one season—and one of them will likely receive that designation again this season.

Kahleah Copper

If there’s any player on the Sky that Wade could end up regretting letting go, it may be restricted free agent Kahleah Copper.

Copper provides ball-handling and scoring off the bench that the Sky simply don’t have elsewhere on the roster. Gabby Williams made progress there last season, but it’s unclear whether that role was simply due to a lack of options at point guard or if it is a future niche for Williams.

In either case, Copper is a bona fide scorer right now, and she seems primed for both a bump in pay and minutes in the near future. The Sky would have little chance to replace her impact this offseason. Nearly 46% of Copper’s field goals were unassisted—of Sky players who averaged 10 or more minutes per game, only Vandersloot and Williams created for themselves more. Copper is also a smart, if conservative, defender who provides staunch perimeter play for the Sky.

She is the perfect player to spell DeShields as the Sky hardly skip a beat when switching between the duo’s playstyles. Wade would have to either pick up another wing who fits in a different vein of play or try to replace Copper’s production elsewhere on the roster. She is also only 25 and could play a big part during the next era of Chicago basketball.

But Copper isn’t a guaranteed star by any means. The 6-foot-1 wing was inconsistent at times for Chicago last year, and she struggled to impact the game on offense when her shot wasn’t falling. She will need to either add a more reliable 3-point shot or take a step forward as a rebounder or passer if she’s going to play a bigger role with the Sky.

It is also a fair argument that the Sky can afford to lose a wing more than they can afford to lose a true forward-center combo like Stefanie Dolson or Astou Ndour.

While Copper can comfortably guard twos and threes, she only played spot minutes at the four. DeShields, Quigley and Vandersloot are all locks to play something in the realm of 30 minutes a night, and Gabby Williams can contribute at a variety of positions. Given the fact that Katie Lou Samuelson, who is on a bargain rookie contract until 2022, should also be in the mix at the three if she can improve, Copper may be the odd player out on circumstance.

Unless Wade has already decided to pay Copper any amount necessary, her future with the Sky will almost certainly come down to the offer sheets she gets from other teams, as well as what kind of deals Dolson and Ndour are seeking.

Jamierra Faulkner

Restricted free agent Jamierra Faulkner could fill a much-needed role for the Sky as a backup point guard.

The only other viable bench option at point guard right now is Gabby Williams, who is still developing as a true play maker. If Chicago loses out on one of its bigs this offseason, it may become a necessity to return Williams to the front court. In that case, picking up a reliable point guard will become a must for James Wade.

But the biggest concern for any team evaluating the 27-year-old guard is her injury history. She has only played 30 games in the past three seasons due to a series of knee injuries. The Sky eased her back into the rotation last season and she only averaged 5.5 minutes per game in 13 regular season games.

In those limited minutes it’s hard to tell just what Faulkner’s impact will look like after her injuries. Faulkner, however, does present an in-house guard who not only knows Wade’s system with the Sky, but is also spending time under at Russian club UMMC Ekaterinburg where Wade coaches. She may be the perfect element to Wade’s desire for continuity and stability for the upcoming season.

Stefanie Dolson

Things get much dicier for the Sky when it comes to decisions surrounding their front court.

Stefanie Dolson is an unrestricted free agent this year and the most proven player of Chicago’s free agents outside of Quigley and Vandersloot. She is also likely to see a significant pay bump this offseason as well. Dolson is one of the few realistically available bigs this offseason that can start on most teams, which will give her plenty of bargaining power.

Dolson averaged 9.3 points, 5.6 rebounds and 2.2 assists while shooting 51.9% from the field and 36.1% from three on 2.4 attempts per game last season. Offensively, she is the ideal stretch big for Wade’s offense.

She sets hard screens and is a great target in pick and pops with Vandersloot. Her range draws opposing teams’ rim protectors away from the basket, opening up driving lanes for the Sky’s slashers, and she works well as a trailing big in transition. Dolson is also credited as a key contributor to Chicago’s positive culture change last season under Wade.

But she also averaged a career worst 3.7 personal fouls per game, frequently limiting her minutes, despite the overall drop in foul calls in 2019. Dolson played 20 minutes or less in six different games this past season—for comparison that only happened to her three times from 2017 to 2018. Wade will need to consider availability in his decision to possibly re-sign Dolson.

The seventh-year post returning to a foul rate more in line with her career average would help matters, but the Sky could be in trouble if she doesn’t. The vulnerability of Chicago’s front court reared its head last season when Jantel Lavender suffered a foot fracture, but Astou Ndour was there to fill the starting role seamlessly.

Prioritizing Dolson could mean the departure of Ndour, leaving the Sky without the luxury of a deep front court. Even assuming Lavender returns to play without a hitch—a tall expectation for any player coming off a foot injury—Chicago won’t be able to afford for its front court players to miss much time.

The timeline of re-signing Dolson complicates matters more than anything. Unless Wade throws the kitchen sink at Ndour and Copper, which would likely preclude a Dolson return anyway, both players will likely want to test restricted free agency first. Dolson, on the other hand, is a veteran free agent entering a market that just acquired a lot of cap space it didn’t have before. It would be unrealistic to expect her to wait before capitalizing when the wells could dry up quickly.

Astou Ndour

Restricted free agent Astou Ndour will almost certainly come on a cheaper contract than Dolson, but she is far less proven.

Prior to this season, Ndour had only averaged more than 14 minutes per game once in her four-year career. While reliable, she has almost exclusively played as a role player. Add that to the fact that she is also likely to continue missing time in the future due to Spanish national team commitments and it’s clear why she is the riskier option for Wade.

But Ndour showed the type of player she might be given a bigger role. Ndour averaged 10.7 points, 7.1 rebounds and 1.1 blocks as a starter, and she put up 16 and 17 points in the Sky’s two playoff games. She is a versatile big who knows how to use her length to alter shots and gobble up drivers, and she’ll only be turning 26 at the end of the 2020 season.

She hasn’t done it at a high volume yet, but she has also shown she can stretch the floor out to the 3-point line, and has flashed some impressive shots from the post. Highlights like this one showcasing her touch only further the temptation to bet on her ability.

And that’s a big part of both the allure and risk of Ndour. Is she a player whose game can scale up as a starter for a full season or is she somebody best suited as a role player? And how much money is she worth in either of those scenarios?

It will only take one team to take an expensive gamble on Ndour and force Wade to choose two of Copper, Dolson and Ndour, assuming he focuses on re-signing as many players as possible. Luckily for Wade and the Sky, they’ll have up to four days to decide whether to match another team’s offer sheet to Ndour.

Waiting for Ndour to test the waters of free agency could cost them Dolson, however, if Dolson chooses to sign with another team early into free agency. Such a scenario would almost certainly force Wade to re-sign Ndour to whatever contract she takes, as their front court would become dangerously thin otherwise.

Kayla Alexander

The Sky brought on Kayla Alexander to a number of short-term deals after Lavender’s foot injury. She averaged 3.0 points and 2.3 rebounds in just under seven minutes of play per game.

While the seven-year veteran has a reputation for her positive locker room presence, she only appeared in three games last season and is unlikely to be back with the Sky in free agency. The Sky have the eighth pick in the 2020 draft and Wade seems more likely to look for a rotation big there instead.

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