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2019 Season in Review: Despite its heartbreaking end, the Chicago Sky had a season to remember (and learn from)

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If the Chicago Sky can make that big a leap from 2018 to 2019 with the same core, the possibilities are endless for 2020. Here’s how the Sky got things done this season.

Chicago Sky v Washington Mystics
The Chicago Sky improved to 20-14 in 2019, earning their first playoff berth since 2016 — and much more.
Photo by Ned Dishman/NBAE via Getty Images

The way the Chicago Sky’s 2019 season ended was cruel, unforgiving — the stuff of nightmares. No team wants their season to end without a championship, but falling in a single-game elimination on a heroic half-court heave after an uncharacteristic error from one of the league’s best passers definitely leaves a bad taste in one’s mouth.

But unlike recent seasons for the Sky, that was in spite of the excellent season they had — not indicative of a disappointing one. The Sky had a lot going for them this season.

Let’s dive right in:

James Wade, Coach of the (First) Year

The Sky had been through the wringer, coaching-wise, over the past few seasons. Pokey Chatman was fired in 2016 after six seasons, Amber Stocks in 2018 after two seasons. Chatman had led the Sky to four straight playoff appearances prior to her dismissal, while Stocks saw the team through two losing seasons and a playoff drought.

Enter Wade, whose desire to get better at coaching drove him to seek opportunities overseas in addition to the WNBA assistant coaching jobs he held prior to 2019. Over the 2018-19 offseason, he was an assistant coach for EuroLeague champion UMMC Ekaterinburg, in Russia, where he coached his future Sky point guard Courtney Vandersloot.

Things started looking up right away for the Sky, despite a winless preseason. The team won six of its first nine games, something it hadn’t done since 2013 — including its home opener against the defending champion Seattle Storm. A four-game losing streak midseason was quickly overcome, and the Sky only lost as many as two games in a row once more the rest of the season. By the end of the season, the Sky had reached the 20-game win mark for the first time since 2015, a seven-game improvement from 2018.

Wade inherited all five starters from last season, the biggest change coming in the acquisition of Jantel Lavender from the Los Angeles Sparks. He opted to slot Lavender into a starting spot alongside Courtney Vandersloot, Allie Quigley (both of whom Lavender was close with beforehand), Diamond DeShields and Stefanie Dolson. And when Lavender went down with injury, Wade brought in Astou Ndour to start in her place, and the transition was nearly seamless.

After all that maneuvering, overall improvement and much more, Coach of the Year seemed in the cards — and it ended up being a fairly decisive vote.

Courtney Vandersloot dazzled

Of course, one of Wade’s greatest assets toward his successful first season was his veteran point guard. Not that he didn’t know what Vandersloot could do already, but collecting 5.8 assists per game for EuroLeague champion UMMC Ekaterinburg under his coaching still made a good personal first impression.

Then, of course, came the 2019 WNBA season.

First, the big marks: Vandersloot led the league in assists per game for the third straight season, her mark of 9.1 breaking her previous WNBA record of 8.6, which she set last season. She also became the first player in WNBA history to reach 300 assists in a season.

Vandersloot also maintained her scoring prowess, averaging a team-third 11.2 points per game. And while she didn’t quite make it two seasons in a row with a triple-double, she still grabbed a career-high 4.3 rebounds per game. She also reached a career-high in steals, with 1.4 per game.

While Vandersloot is well-known among Sky fans for never quite getting the recognition she deserves — namely, at the All-Star level — this season provided a little bit of both: Vandersloot was named an All-Star for the first time since her rookie season, and even collected the two first-place MVP votes that didn’t go to Elena Delle Donne.

Three All-Stars — but a team’s worth of support

Besides Vandersloot, DeShields and Quigley were also named WNBA All-Star Reserves this season. (Quigley ended up getting to start in A’ja Wilson’s absence.) Three All-Stars for the Sky was a tie with the Las Vegas Aces and Minnesota Lynx for the most of any team, and it was the most for the Sky since 2013.

While Quigley wasn’t successful in defending her Three-Point Contest title, DeShields prevailed in the newly-revamped Skills Challenge, assuring at least one piece of hardware would come back to Chicago with the team.

Speaking of the team, all but three Sky players headed to Las Vegas in support of their All-Star trio. Cheyenne Parker credited Wade with the “positive shift within the organization,” while Lavender said of the decision, “Everybody was super close and everybody supported each other, so it’s good to be back on a team where everybody wants to support each other.”

Quigley scored a Sky-high 14 points, including going 4-of-8 from three, DeShields had 13 points and five rebounds and Vandersloot scored seven points and dished eight assists.

Plus, well, this:

Looking ahead

For the most part, if things didn’t dramatically improve for the Sky in 2019, they held harmlessly steady. No one player completely tanked, and DeShields continued her ascent into early superstardom with another standout year.

This, unfortunately, meant that the Sky rookies who made the team didn’t see much of the court. Chloe Jackson was waived on Aug. 22 after appearing in just eight games, while No. 4 overall draft pick Katie Lou Samuelson only averaged about eight minutes in the 20 games she played — though a wrist injury interrupted her early professional development.

No longer a lottery team, the Sky have the No. 8 pick in the 2020 draft, as well as two third-round picks. In another stacked draft class, eighth overall could yield a future superstar. But in the meantime, sticking with what they have could still get them far, especially as the team continues to grow under Wade.

The Sky certainly wanted a better ending to this season. If a title wasn’t in the cards, maybe a decisive loss would have been easier to take than what happened. But at the end of the day, it really is just one more learning experience for a team that faced so many of those this season.

That playoffs loss is one the Sky will take if it means that they use this heartbreak as fuel next year, armed with everything they’ve learned, poised to replace that one bad memory with a whole new season of good ones.