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The 10 Greatest Chicago Sky Players of All Time

ByEdwin Garcia|@SkyInTheChi| December 6, 2020

When it comes to the Chicago Sky’s best players of all time, it’s really hard to pick. And that’s a good thing, because it means in the WNBA team the Chicago Sky’s 15 years of history, they’ve had some incredible players represent Skytown.

We’re talking three-point contest winners, assists leaders, all-stars, and top draft picks — all who went on to have memorable careers. So to celebrate these inspiring players, today we are taking a look at who should make the list of all time greats. 

Discover the best Chicago Sky players of all time

Best of lists are always tricky. How can you weigh guards against forwards? What stats rationalize your argument for “best”? How can you take into account the number of years they played for the franchise?

We’ve concluded it’s most helpful to consider the player’s performance only as a Chicago Sky player. Stats matter, but they’re not the only thing. Other components such as individual accolades, the leadership role they played, their improvement while on the team, and how successful the team was with them on it have been factored in as well.

As far as positions go, we’ve neutralized their roles. And instead, have relied more on the player’s production and their impact on the team. So it’s not about a guard being able to “beat” a forward. It’s more about which had the bigger impact on the team’s overall success. Because if you don’t win, it doesn’t really matter what you did. So with the ground rules set, let’s get into the top Chicago Sky players of all time, starting at the bottom of the list.

10. Stefanie Dolson the most known unknown 

When you think about the current Chicago Sky roster what names do you think of first? Probably Courtney Vandersloot, Allie Quigley, and maybe even James Wade. Here’s a little secret though: You should think of Stefanie Dolson.

Stefanie Dolson has been a member of the Chicago Sky for the past four seasons. And she has been an integral part of the Chicago Sky’s return to form. She’s started in 100 out of the 109 games she’s played in. She’s earned an All-Star appearance in 2017. And she’s averaged 12.2 points, 4.8 rebounds, and 2.3 assists per game. Furthermore, because she’s an established threat down low, it’s her presence that draws the defense, and opens up Allie and Courtney to get off their shots.

Stefanie still has room to rise on this list. She had a down 2020 because she was injured throughout the season. So 2020 is not a good example for how well she can still play. If she produces like she did in 2018 – and if she can get another all star appearance and a ring for the Sky – you can expect her to move up in the rankings.

For now, she is already a Chicago Sky legend and a top ten player for the franchise. To see some highlights from her all star season, watch the video below.

9. Diamond does it 

Diamond DeShields is a shining star for the Chicago Sky. She was drafted third overall by the Sky in the 2017 WNBA draft. And has quickly become one of the most electrifying players in the league. She made the All-Rookie team in 2018 and the All-Star team in 2019. During her three seasons in the league she’s averaging 13.9 points, 4.7 rebounds, and 2.2 assists per game. 

Diamond DeShields’ potential is limitless. With her raw speed, power, and passion for this game, she can go as far as humanly possible in this league. We’re talking WNBA MVP, Hall of Fame, and WNBA Champion. Will she reach that full potential is the question.

So far she’s made significant strides in every season except for her 2020 season which was mired by injury. She’s the youngest player on this list. And if she stays healthy, she will absolutely move up the rankings here. For some footage of how good she has been already, watch the video below.

8. Tamera Young: A Chicago Sky vet

Tamara Young was a staple in the 2010s for the Chicago Sky. She played for the team for seven consecutive seasons. During her tenure with the Sky she was a veteran leader. And was part of the teams that found playoff success which resulted in the Chicago Sky’s only WNBA finals appearance in 2014. Her career per-minute production rating is 10.4, and her she racked up 7.1 points per game, 3.9 rebounds, and 1.5 assists.

Having that length of time under her belt, she’s been a part of the organization for nearly half its existence. You simply can’t write the history of the Chicago Sky without her. To see Tamera Young’s  highlight check out the video the Sky released back in 2011.

7. Jia Perkins is an all-time great! 

Similar to Stefanie Dolson, Jia Perkins doesn’t get enough respect for all she accomplished. She played for the Sky from 2006-2010 and was spectacular. Her best season was in 2009 when she made the all star team and averaged 13.2 points, 3.4 rebounds, and 2.9 assists. She was consistent and productive during a time when the team was anything, but.

She helped be a bright spot during the berth of the franchise. Plus, players like her and Sylvia Fowles helped give Chicago Sky fans a reason to cheer during those early days. Here’s a Jia Perkins interview from back in the day that’s amazing to watch now.

6. Allie Quigley the three-point master

Allie Quigley is the best shooter in Chicago Sky history. She has won two three-point contests. Furthermore, she averages 39.2% from the three her entire career. She’s been growing as a player. And has made the All-Star game for three consecutive seasons. There are so many things Allie Quigley does at an elite level. She’s quick, amazing off the ball, and clutch late in games. 

Allie has played in the WNBA for 14 seasons so it’s unclear how many more years of elite production she has left. Though in 2020 she had 15.4 points per game, 2.9 rebounds, and 2.4 assists. So far, she hasn’t shown any signs of slowing down. If she can add another all star appearance and a ring, she can move up on this list. Here are some highlights from Allie Quigley’s career. 

5. Epiphanny Prince nearly crowned the Sky 

Epiphanny was one of the stars of the Chicago Sky team during the first half of the 2010s. She reached the All-Star game in 2011 and 2013. In 2012, she finished fourth in the WNBA in scoring, and third in free throw percentage. Before having her best season with the Sky in 2013, averaging 21.7 points, 4.2 rebounds, and 3.7 assists. Plus, she scored in double figures on 25 occasions.

Epiphanny played her best season in her illustrious career with the Sky. It’s going to take a lot for anyone to knock her off this list in the future. Watch some highlights of her Chicago Sky years below. 

4. Candice Dupree: First pick ever

Candice Dupree was the first draft pick the Sky ever had. For that alone she’s a part of the Chicago Sky’s history. Candice was the bright spot for the team despite their losing record their first four years. And her workload with the Sky continued to grow — peaking at a high of 34.9 minutes per game in 2009. She’s high on this list because she’s a three-time Chicago Sky All-Star and a beacon of light during the early years of the franchise.

She was a walking bucket, able to drop 16 plus points in her sleep. She appeared in all but one game with the Sky through four seasons before being dealt to Phoenix in March of 2010. Her career is still going strong which is a testament to her professionalism, endurance, and ability on the court. Very few players have had better careers than Candice Dupree. See for yourself. 

3. Sylvia Fowles is one of the best Chicago Sky players

Sylvia Fowles’ seven year run was about as good as it could’ve been. She nearly averaged a double double in points and rebounds throughout her tenure. And she continued to improve offensively and defensively as the years went on.

She was a dominant center who was part of the best Chicago Sky team ever. Sylvia was an absolute workhorse for the Sky. In her entire Sky career, she started all but 9 games that she played in. 

We’re generally not talking about the seasons outside of the Chicago Sky years, but after her Chicago Sky years were over, she went on to Minnesota and won two rings. Her impact in the W and her importance to the Chicago Sky organization has only grown with time. Sylvia Fowles is not only a Chicago Sky legend, she’s an all time great in Women’s basketball. Watch her play below.

2. Courtney Vandersloot the point god

If you watch the Sky today you can’t miss her: the leader of the Chicago Sky, the point god herself, Courtney Vandersloot. Perhaps the greatest passer in WNBA history, Courtney has her name on all assist records available including, most assists in a game (18), most assists in a season (300), and highest assist average for a season (10). She runs the Chicago Sky’s fast paced offense. Plus, she has led them into a resurgence that has put the team back into the playoffs for back-to-back seasons. 

She’s played all ten years of her career with the team making her Chicago’s very own, as well as the player with longest time as part of the organization. Add her two All-Star appearances for good measure and you get the second best player to ever wear the Skytown colors. When she finally wins a ring, she’ll earn our number one spot. So be sure to watch the point god in action in the video below. 

1. Elena Delle Donne and what could have been 

Elena Delle Donne is the greatest player in Chicago Sky history. She was drafted by the team in 2013, and immediately made them better, earning Rookie of the Year in the process.

Offensively there is nothing that she can’t do. She has a complete game. She can reach any spot on the floor, hit mid range jumpers and three point shots, and she’s a strong finisher at the rim. Her numbers with the team were 20.2 points, 6.25 rebounds, and 1.5 assists per game. 

Elena’s time with the Sky isn’t all positive. She demanded a trade from the team and was traded in 2017. Unfortunately, she didn’t want to be part of the team, and that hurts everyone involved with the organization. Still, she was the best player to ever play for this team. And although there is pain in reflecting on what could have been, we should be happy for what it was. A star player not even hitting their prime and leading this team to the WNBA Finals.

She was the best player the team has ever had. And it’ll take a Hall-of-Fame caliber player  winning a ring to ever knock her off our number one spot. So take a look at the greatest Chicago Sky player of all time. 

Watch the greatest Chicago Sky players of all time

Now you know the ten best Chicago Sky players of all time, and a little more about how each of them has contributed to growing the women’s game. We can’t wait to see what current players crack this list in the future.

In the meantime, enjoy even more show-stopping action with the greatest Chicago Sky moments. Or create your own team of the best Chicago Sky players ever with our free team maker.

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