Column: Why the Chicago Sky, from the top down, need Skylar Diggins

Chicago Sky overhaul roster after draft and Angel Reese trade

ESPN analyst Meghan McKeown breaks down the Chicago Sky’s draft picks, new additions like Gabriela Jaquez and Rickea Jackson, and what success looks like after a major offseason shakeup.

Every time Skylar Diggins looks up and see the Sky’s 2021 WNBA Championship banner, she’ll have to remember her part in that. 

She doesn’t get a ring from that. To her dismay, she was on the other end of it with Phoenix.

The Sky beat Phoenix 3-1 to win the franchise’s first WNBA title. Since then, the Sky have dropped to the bottom of the league and have remade the team’s roster for a second time. In doing so, the Sky had a checklist.

"We were looking for more fire," Sky general manager Jeff Pagliocca said. "We have it now."

Sure, getting back there requires star power and talent. It requires players who compete at a high level, and don’t accept anything less than that.

Welcome, Skylar Diggins.

The 14-year veteran guard is known for her competitive edge around the league. Some can misconstrue that with being too much to handle. What that really means is Diggins wants to win, and will make sure everyone else is on the same level. Not just the immediate roster, but the coaching staff and front office, too.

That’s what the Sky needed.

"Our standards have to be strong," Diggins said on Wednesday. "If you have strong standards, that demands respect."

The Sky introduced Diggins on Wednesday. She presented herself as a grateful veteran who chose Chicago to be closer to her family in South Bend. That’s why she had conversations with the Sky two years ago in free agency before signing with Seattle.

Now, she joins the Sky on a multi-year deal under a new CBA that will pay her as she’s worth.

Don’t take anyone else’s word but Diggins on how much she’s worth.

"I’ve been an All-Star everywhere I’ve been," she said.

While the Sky might be paying her to be the ultra-productive player she is – Diggins is a franchise leader in assists for the Wings, Storm and Mercury franchises – the Sky are getting the one thing they sorely need, and that’s someone who won’t be afraid to light a fire under someone that needs it.

The Sky needed it last year as they tumbled to a 10-win season. Head coach Tyler Marsh might’ve needed it a couple of times during his rookie season. Pagliocca might’ve needed it, too. He joked about not wanting to hear from Diggins if they didn’t get players who could contribute to winning right away.

But that’s what would have happened. Diggins made it clear she’s going to be a teammate that challenges the entire organization. 

"I wouldn’t say I’m an easy teammate, but I’m a good teammate," Diggins said. 

The translation there is Diggins will make sure the team is striving to be its best everyday. The Sky haven’t had a player at that level of competitiveness since Parker was in Chicago.

Players will say they want to be that type of player. Diggins is that type of player. The Sky will be better for that.

"Skylar has been around to where she knows the fake from the real," Marsh said. 

Diggins is as real as you can get. That helps when the team wants to win instead of rebuild.

"What 'winning now' means is getting ultra-competitive players here who won't live with anything less than success," Pagliocca said.

It’s one thing to say the Sky are in a win-now mode. Pagliocca said that last year, too. The season bottomed out quickly.

Step one to being a win-now team is getting a player like Diggins. That’s a signing that will make a difference when adversity strikes.

This time, the Sky will have a player who’s been around the league long enough to know how to right a ship and knows how to guide a team according to the vision laid in front of them.

Diggins wouldn’t be here if the Sky didn’t also have the vision to acquire players like Azura Stevens and Rickea Jackson. Now that it’s all coming together, the Sky will be better for having a player like Diggins steering the ship.

Even though the league is different now than it was a year ago, Diggins won’t accept anything less than winning. The Sky, from Pagliocca down to the final roster spot, should follow where she leads.

"This free agency is a little different," Diggins said. "It was the right time. I’m bought in to the vision."