The Chicago Sky hit a limit in their first excursion of the post-Angel Reese era.
Beyond the WNBA's fateful eight lies a searching seven.
The WNBA has entered the final week of its regular season but the eight-team playoff field has long been established with no more than four games left on every squad's docket. The remaining seven are left to pick up the pieces for next year, forced to ponder their fates as they watch the league's 30th postseason from the sidelines.
With that in mind, Ballislife looks into the futures of these voyages of the damned and what kind of waters they'll traverse on the trip ahead. This series will be presented in the order of each team's elimination from playoff contention.
We come to the penultimate portion of our focus on non-playoff teams, with part six centered on the CHICAGO SKY ...
Team: Chicago Sky
Record: 15-27 (and counting)
Last Playoff Appearance: 2024
Date of Playoff Death: August 23
What Went Wrong
The cease of Reese failed to bring about an end to the Sky's playoff drought.
The Angel Reese era produced innumerable headlines but not many wins. Dissatisfied with such an output and perhaps eager to atone for drafts gone by, Chicago traded Reese to Atlanta for future first-round picks in 2027 and 2028.
It likely stung to trade a franchise face for no named assets but the deal at least provided an opportunity to bury previous mistakes: by the end of this season, only two of Chicago's seven first-round draftees in the 2020s are still on the team (Kamilla Cardoso and new entrant Gabriela Jaquez). Two are out of the league (Shyla Heal, Ruthy Hebard), another joined Reese in opportunities abroad (Hailey Van Lith) and the outlier (Ajsa Sivka) went back to school.
Chicago was able to bring on the potential-packed Jaquez thanks a 2024 trade with the Connecticut Sun (one headlined by Marina Mabrey's departure). But Jaquez's early output was hardly any consolation for what was lost in their regularly-scheduled second slot, which sent mighty Olivia Miles to Minnesota in a 2025 draft night swap where Illinois' prime import was the since-departed Van Lith.
Rickea Jackson tonight 🔥
— Women’s Hoops Network (@WomensHoops_USA) May 16, 2026
• 29 points
• 6 rebounds
• 3 blocks pic.twitter.com/lvnF0JbFWj
Rickea Sportage
If nothing, the Reese trade could've been a nice time to regroup and prep for the future. Beyond a 37-year-old Courtney Vandersloot, the Sky had little in terms of established headlining talent and it wasn't going to grant such duties to Cardoso after ditching the similarly-skilled Reese.
But the Sky followed the Reese deal up with the windfall of an intriguing one-on-one swap: taking advantage of the equally desperate Los Angeles Sparks' situation, Chicago acquired sensational SoCal project Rickea Jackson, who made a name for herself despite lingering in the same draft class as Reese and Caitlin Clark.
Trading for Jackson in a one-on-one swap for veteran specialist Ariel Atkins tipped off a Chicago activity list that would put Ferris Bueller to shame: the Sky applied for a playoff residency by adding more decorated veterans to their rookie-lite ranks, such as DiJonai Carrington and Skylar Diggins (who was likely looking to push a playoff case after escaping Seattle's rebuild). The backcourt binge only continued with the drafting of Jaquez and the last-minute addition of Natasha Cloud, the culmination of an apparent attempt to re-discover finesse at the top of the key after trying to push Cardoso and Reese as a headlining duo.
It likely wasn't enough to knock any current penthouse dweller out of their lease but there was realistic hope that the Reese era could begin with the end of the team's two-season playoff drought.
Sky Fall
The good news is that Jackson defined the middle initial of MVP perfectly. The bad news is that she played but four games before the injury bug found her after already biting Carrington, whose Windy City debut was delayed by foot surgery in April.
Chicago won three of its first four with Jackson leading the way but a torn ACL on May 17 marred an otherwise landmark evening that produced an upset win over the Minnesota Lynx. The Sky then fell to the tune of five consecutive losses to start life after Jackson and wound up dropping all but one of the first dozen in that doomed period. By the time help arrived from a most unexpected source, they were well out of the playoff chase and already looking ahead to 2027. Diggins has long medically excused herself from the proceedings, as a knee injury has kept her sidelined since early July.
There's no shame in getting tripped up by an injury to star talents. Heck, that could charitably explain why the Sky and each their playoff-free sisters will be watching the playoffs from home. But, in a more uncomfortable truth, it appeared that the Sky, in their rush to cease the Reese era, forgot to fully fill in the middle step before reaching the profit stage.
No Rebound
The most dangerous aftershocks of the Reese trade were appropriately felt inside: despite the best efforts of Cardoso (who admittedly had little issue carrying her end of the bargain to the tune of career-bests in most major metrics) and a returning Azura Stevens, no season-long Chicagoan averaged more than four rebounds a game and the Sky ranked dead-last in rebounds against ... after allowing the third-fewest with Reese on board last season.
As lampooned as the concept of Reese's appropriately self-described "mebounds" has been, Chicago's lack was no laughing matter this year: the Sky fell to 12th in second-chance points after going no worse than top five in each of the prior two tours. As if missing out on Miles didn't sting enough, the Sky was trapped in a relative no man's land when it came to adjusting their post picture: the immediate preceding picks before Jaquez were Awa Fam and Lauren Betts, and it has to sting to watch Reese work with late first-round selection Madina Okot in Atlanta.
The backcourt surplus also got a little overbearing, especially when one considers the franchise's long-term prospects: Vandersloot has no doubt earned a retirement tour but the Sky appears far too keen to make it a point of emphasis rather than a subplot. The Sky drafted Jaquez and then added both Cloud and Diggins, all while trading for Jacy Sheldon. That created a logjam in the backcourt that made Van Lith expendable and added yet another task to the to-do list of head coach Tyler Marsh, who had enough to worry about beyond balancing a minutes spreadsheet.
Top Silver Lining
All kidding aside, the true shame of it all is that Jackson showed she had headlining mettle in an admittedly miniscule sample size.
Through the first week of play, Jackson was one of eight players averaging 22 points, one of three to pair that with at least six rebounds, and the latter of two (next to Breanna Stewart) to add multiple assists on top of that. She was also getting more tenacious on defense: she put up seven blocks in four total appearances after getting 14 in each of her first two tours. For a team that opted to shake up its identity, it's at least somewhat assuring to see Jackson pass her early tests as a top option.
Rickea Jackson tonight 🔥
— Women’s Hoops Network (@WomensHoops_USA) May 16, 2026
• 29 points
• 6 rebounds
• 3 blocks pic.twitter.com/lvnF0JbFWj
Taylor's Swift
The backcourt logjam was rendered somewhat more tolerable by finding one of the most intriguing undrafted diamonds, namely Louisville alumna Sydney Taylor, who was added hours before Jaquez's selection.
A strong preseason saw her kept on the team over Van Lith and she was a starting five staple before the year hit its midway mark. In an era of heightened draft parity and international RINOs (Rookies In Name Only) that get extensive experience overseas, Taylor (who put up stints in Lithuania and Poland after going undrafted in 2024) kept pace with the fantastic freshmen that made their debuts alongside her and is on pace to set the undrafted rookie record for WNBA scoring average. That's a mark that Sylvia Crawley of the original Portland Fire has held since the year 2000.
The Sky had to exhaust any form of player development following misfires at the draft and Taylor's work stood as one of the most pleasant surprises in recent WNBA memory. That should serve as a feather in the respective caps of Marsh and Latricia Trammell, the former Dallas head coach who brought her brand of development up north this season. There's still work to do on Taylor's end, but the idea of pairing her with Jackson at the height of their respective powers is a concept that will serve as the support of Chicago's hardwood hopes for the immediate future.
Looking Ahead
Unrestricted Free Agents: Rachel Banham, DiJonai Carrington, Natasha Cloud
Reserved Free Agents: Sydney Taylor
Can't endure draft disappointment if you have no major picks? The Sky appear to be taking at least something of an inactive approach: the good news is that they have two first-round choices, as the first dividends of the Reese yield come by next year. The bad news is that Chicago has no active raffle ticket in the JuJu Watkins sweepstakes, having lost what are currently the third-best odds in a 2025 pick swap with Washington that also acquired the departed Atkins.
Chicago does at least have something of a plan, one that has potential thanks to Jackson and Taylor's early returns: eight veterans are under contract for next year and the early breakouts (not to mention acceptable progress from Sheldon and Aicha Coulibaly, both of who earned extra opportunities as things got further out of hand) might be enough to convinced an embattled management group to keep things static in lieu of another teardown.
The Sky could sit in particularly good shape among their eliminated sisters if they're able to clear any and all air with Diggins: the lasting veteran showcased apparent displeasure with a removal from the starting five and some viewed her as prime trade deadline bait after that removal. However, the Sky made no major attempt to shift her services and she remains under contract for next season. A budding big three of Diggins, Jackson, and Taylor would be a fantastic foundation as the Sky seeks to reclaim its former glory.
Is There Hope?
One can hardly blame Sky fans for being jaded by this season and the fact that they'll have to watch another potential-packed lottery from the sidelines despite doing all the work. But Taylor's unexpected breakout and Jackson's tease hint that a full-on teardown isn't necessary and that a return to the playoffs is possible provided the right complementary pieces are added.
It'll be up to Marsh ... or a potential successor considering the lack of standings progress since Teresa Weatherspoon was controversially removed from the head coaching post after a single season ... to cash in on the bittersweet benefits of what eventually became an R&D tour. Whether it was enough to fully convince Diggins to stick around remains to be seen.
It's probably not the type of progress that Sky supporters wanted to hear at this point on the franchise timeline, but the fact that things aren't worse considering the sheer number of draft debacles is progress as is. That type of work, however, gets less heartwarming with each passing year off the bracket so the Sky will need to make some undeniable steps forward next time around. Jackson and Taylor should be recognized for paving a softer path in that regard.
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Geoff Magliocchetti is on X @GeoffJMags
