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How Much Does Lori Lightfoot Love The Chicago Sky? An Investigation

Screenshot: Chicago Sky

The WNBA isn't quite the ethical beacon it pretends to be, but I'll admit this: You don't have to worry much about old-school corruption when it comes to this league—no shady arena deals, no city council feuds, no unkept development promises. Last week, Anaheim's mayor resigned after an FBI probe exposed his plans to ask Angels execs for campaign donations in exchange for help with the Anaheim Stadium sale. The news got me thinking about the mayor most likely to be caught up in some WNBA-related civic scandal, and I didn't have to think too long. It is absolutely Lori Lightfoot, mayor of Chicago and WNBA sicko.

Lightfoot, who announced her bid for re-election yesterday, is a regular at Chicago Sky games and a longtime season ticket holder. One Chicago-based Defector staff writer recently spotted her delivering the opening remarks at the Sky's championship banner-raising ceremony. Before you dismiss it as token mayoral interest in local teams, know that Lightfoot hasn't treated them all with warmth. In response to the Bears' bid on stadium land in Arlington Heights, for example, she issued a statement saying the Bears should "focus on...being relevant past October." Last fall—two weeks after Lightfoot signed a proclamation making Sept. 16 "Candace Parker Day," two weeks before the Sky won the 2021 WNBA title, and a week before the Bears stopped being relevant—I sent a public records request to Lightfoot's office, curious about the mayor's relationship with her city's WNBA team.

As it turns out, she may have had some hand in building it. In December 2020, just before the holidays, Sky owner Michael Alter emailed Lightfoot's wife, Amy Eshleman, asking a favor. "The sky, as you know, barely made it through a harrowing season: financially, EXTREMELY painful; on the court, disappointing since we strongly believed that if we stayed healthy, we would have competed for the championship," Alter wrote. "This upcoming season will continue to be very difficult. There are, however, some exciting things in the works which, if we can pull it off, will greatly help the growth of the league. (if you're interested, I'd be happy to fill you with more detail)."

Alter went on to say he hoped that Lightfoot could come out in support of an amendment to sports wagering legislation that had passed the previous summer. The initial bill gave Chicago's major men's professional teams the opportunity to apply for sports betting licenses; the proposed amendment would allow the Sky to do so, too. Eshleman forwarded the email to Lightfoot and told Alter to expect a call from the mayor. "I would love to hear about your plans for the team and the league when you have some time," Eshleman wrote in her response.

It wasn't a successful interaction in any sense: Lightfoot never called Alter, the amendment still hasn't passed, and Alter would eventually be fined $5,000 by the Chicago Board of Ethics for failing to register as a lobbyist when this email turned up in a public records request made by the Chicago Tribune. But in late January, Alter returned to the first lady of Chicago with a different ask. "i havent heard yet from the mayor on regarding the sports betting, but i'm actually writing about something else," he wrote. "CANDACE PARKER."

Parker, the Los Angeles Sparks star raised in nearby Naperville, was a free agent that offseason and not eligible for core designation, the WNBA's equivalent of a franchise tag. She'd had "several positive conversations" with Alter and Sky head coach and GM James Wade about signing with the Sky. Alter wrote, "do you think the mayor would be willing to give candace a call -- or send her a text, encouraging her to come play for chicago? we're pulling out all the stops we can think of to make her feel 'home.'"

This time, Lightfoot mustered a level of interest and urgency she hadn't shown at all toward the gambling thing. She responded the next day to tell Alter she was "happy to help you always, and specifically on this mission." She suggested connecting by phone or by Zoom to talk more about making the call and even copied a deputy mayor, her liaison to the city's sports teams. "If Candace does come to the Sky, we would love to partner with you make this a really big deal to drive fans to watch and come see games," Lightfoot wrote.

Alter promised to put the two in touch and asked whether he could forward the email exchange to Parker. Lightfoot agreed, and her enthusiasm in writing alone may have done the trick. Two days later, on Jan. 27, Alter sent Lightfoot an update: "She’s coming!! Thanks for the help! I’ll connect you two soon."

Eshleman, thrilled, told Alter and Lightfoot they should think "creatively about maximizing this news." She suggested getting Lightfoot a jersey with Parker's name and number on it so the mayor could make a welcome video. Alter asked Lightfoot whether she'd be interested in participating in a virtual press conference announcing the signing, and mere minutes later, Lightfoot said she was in.

A virtual Candace Parker signing event was an odd place for an embattled mayor to be. The press conference happened on Feb. 2; at the time, Lightfoot was in the middle of a highly public showdown with the Chicago Teachers' Union, whose proposed safe reopening measures she had rejected before threatening to lock the city's teachers out. One email exchange before the Parker press conference suggests Lightfoot knew the optics were weird, too. "We need to make sure that their media person says that the media questions should be on topic," she wrote in an email to her aide Kelsey Nulph and Eshleman. Nulph responded, "You’re not taking questions - only the people listed are," copying the portion of the agenda that said Alter, minority owner John Rogers, Wade and Parker would take questions. "But if I am still on the screen, then reporters may think I am," Lightfoot said.

Lightfoot escaped the press conference without having to take questions. In an email to Alter after the event, she reiterated her excitement: "Candace is so well spoken and you can see the sincere passion about coming home." Various Outlook Calendar reminders indicate that Lightfoot attended games throughout the season, and she paid the team special attention during their postseason run.

She wanted everyone to pay attention. The day after the Sky beat the Minnesota Lynx in the single-elimination second round of the WNBA playoffs, Lightfoot sent an email to her director of digital strategy, her deputy director of digital strategy, her communications director, and her chief of staff with the subject line, "Chicago Sky Playoff Victory." She wanted to know, "Did we put somrthing out on social media about the Sky victory last night? If not, we should do so today." (They had.) The next night, after the Sky took Game 1 of their semifinal series against the Connecticut Sun, she emailed the group again, this time with "Sky Win Tonight" in the subject line. "The Chicago Sky just won a double overtime game against the Connecticut Sun at the Sun's home court in a best of five semi-final," Lightfoot wrote. "This win was a big upset. We should give them some love."

Ximena Larkin, the director of digital strategy, told Lightfoot they were already on it, and added that Courtney Vandersloot had set a WNBA playoff assist record. "I know!" Lightfoot replied. "Great stuff all around."

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