First Round Team Preview: Chicago Sky

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It was the best of times, it was the worst of times, it was the age of the 5-out offense, it was the age of the turnover-riddled team, it was the epoch of slaying Aces, it was the epoch of being slain by New York, it was the spring of hope, it was the winter of despair. 

Sky fans entered 2020 with dreams of double byes and a Finals trophy. But Chicago natives better be up to snuff on their Dickens because it’s been a tale of two seasons for James Wade’s bunch. 

Chicago began the season 9-4, maintaining its roll despite a few nagging injuries and much tough competition. That was before Diamond DeShields and Azurá Stevens suffered season-ending injuries and later left the Wubble. Without those two major contributors, the Sky finished the regular season 3-6, suffering a four-game losing streak as they slipped from the top four all the way to sixth place. 

Does Chicago have enough firepower to down the Connecticut Sun, tonight at 7 PM in a single-elimination first round playoff game? Let’s dive right in. 

It’s hard to glean a whole lot from Chicago and Connecticut’s two regular season meetings, as they both occurred pre DeShields/Stevens injuries. We can glean some clues from the proceedings, however. 

For instance, the first time these teams met – a 100-93 Chicago win on August 8th – the Sky went small late with Gabby Williams playing the 4. This forced Sun head coach Curt Miller to alter his own rotation, putting Alyssa Thomas at the 5 and DeWanna Bonner at the 4. My game notes from that afternoon read, “Gabby at the 4 is better in some matchups for Chicago, including this one.” 

Brionna Jones has super quietly logged a fantastic season. It’s a win for the Sky if they can send her to the bench and force Miller to dip deeper into his guard/wing rotation. Connecticut didn’t have Briann January the first time these teams played, but they did have Bria Holmes, who is now out for the season with a knee injury. The Sun go as Thomas and Bonner go. Forcing them to chase shooters across the floor would go a long way in tiring them out come crunch time. Bonner and Thomas finished the season ranked fourth and fifth respectively in minutes per game. The three players who saw more action – Napheesa Collier, Arike Ogunbowale, and Betnijah Laney – are all younger than Bonner (33) and Thomas (28). 

That brings me to Cheyenne Parker. There have been so many marvelous performers this year that I haven’t yet gotten to profile Parker, which is a shame. Not only is she a delight; she’s arguably been one of the 20 best players in the WNBA this season. It will be fascinating to see how Wade utilizes Parker and Stefanie Dolson tonight, and whether rookie Ruthy Hebard receives any significant minutes. The likely answer? Yes. Chicago’s frontcourt is just too thin after Stevens went down, even accounting for the mid-season addition of Stephanie Mavunga, who is questionable with a knee injury. 

If Chicago wants to advance, Parker needs to be the primary center. It’s that simple. Dolson provides a fantastic spark off the bench. Her passing, screen-setting, and shooting form a lethal offensive combination. But Parker shot nearly 47 percent from three this season on 1.6 attempts per game! Her drastically improved stroke and clear defensive advantage over Dolson makes her the key player to watch for in this matchup. It’s also worth noting that Parker has been Chicago’s most reliable “clutch time” player along with Courtney Vandersloot and Allie Quigley, er, VanderQuigs. On both ends, Parker has made numerous decisive plays in the final few minutes of tight games. 

Watching Vandersloot and Parker run pick-and-rolls against Jasmine Thomas and Alyssa Thomas will be an absolute blast. AT is one of the best defenders in the game and puts on an absolute clinic guarding these fundamental actions. Vandersloot, as I’m sure you’re well aware, is the best passer in the game and devastating when paired with a player like Parker who can launch from deep or unfurl a variety of stellar moves attacking the basket. If Chicago lets AT dictate its looks, Wade’s group is in for a long night. If the Sky are able to attack with consistency and keep the ball moving without turning it over – a key problem for them late in the season – then their fourth ranked offense will be able to puncture Connecticut’s fourth ranked defense. 

As is the case in tonight’s second first round matchup between Phoenix and Washington, rebounding will play a large role in determining the victor. Chicago isn’t bad on the boards, but they’re not elite like Connecticut is. The Sun rank second in rebounding percentage. Hebard could be helpful here, as she’s battled with more experienced bigs all season and held her own. The rookie out of Oregon creates second-chance opportunities for Chicago, as does Parker, who ranked in the league’s 92nd percentile in offensive rebounding percentage this year. Wade’s goal likely will be to force Miller into an impossible decision: go big and take your chances with Jones having to guard Parker or Dolson out behind the three-point line, or go small and potentially cede your one clear (rebounding) advantage?

As for Wade’s own difficult decisions, nothing compares to the headaches induced by figuring out how to guard Bonner. Both Kahleah Copper and Williams saw time on Bonner in the regular season, but I suspect Williams will be the primary defender in this win-or-go-home contest. Copper has turned in stupendous performances on both ends this year, posting double-digit scoring totals in 20 of her 22 games and tracking opposing backcourts with tenacity. She just doesn’t have the length to compete with Bonner, and while Williams can’t match Bonner’s wingspan either, she can at least bang with Bonner enough to possibly keep her from maintaining a groove. 

Putting Williams on Bonner would allow Wade to use Copper against Jasmine Thomas. When JT is scoring, Connecticut is a different, far scarier team. Most folks understandably think of Copper’s scoring first when her name is brought up, but she might serve a more important role defensively tonight. Especially with JT not at 100 percent health-wise battling plantar fasciitis, eliminating her as a threat would place a massive burden on the Connecticut frontcourt to put the ball in the bucket. 

Ultimately, this is a make-or-miss league. Wow. Groundbreaking analysis, my guy. You’ve really made a breakthrough here. 

But it’s true! Chicago finished atop the WNBA in both true shooting percentage and effective field goal percentage, metrics that gauge shooting efficiency while factoring in the greater value of three-pointers. It all starts with Quigley, but there are times when everyone in Sky blue is raining down triples. How well will impressive Sun rookie Kaila Charles hold up fighting over screens amid the intensity of playoff basketball? 

Despite its great shooting from the field, Chicago ranked last in the league this season in free throws attempted per game at 14.9. The Sun averaged 20 free throw attempts per game, good for third in the WNBA. It’s not shocking that a jump shooting team trails a frontcourt-powered team in free throw attempts per game. It does bear mentioning, however, because the Sky shot 32 free throws in their win over Connecticut, but when these two faced off again on August 14th, the Sun got to the charity stripe seven more times than the Sky and won, 77-74. 

It’s impossible to narrow 40 minutes of high-intensity, high-stakes basketball down to one factor, but if I had to isolate where this game will be won or lost in the eyes of the Sky, it’s how well or how poorly they will fare in attempting to neutralize Alyssa Thomas. 

If Chicago forces Connecticut to go small and is able to draw Thomas out of the paint, that paves the way for Copper – an outstanding finisher – to drive and Vandersloot to drive and/or kick. Suddenly, offense becomes a breeze. But if Thomas is swatting or altering everything in her sight, Chicago will find itself in way too many late-in-the-shot-clock scenarios. Conversely, will Thomas be able to get out in transition and play point forward, where she becomes one of the most daunting covers in basketball? Or can the Sky wall off the paint, something they haven’t been able to do all that effectively in 2020? Who knows? A bravely taken charge or two could be the difference between boarding a flight out of the Wubble and extending your stay another few days. 

My word, the playoffs are already here. 

It was most certainly the best of times.

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