1. The Most Interesting Man in Chicago

Or at least that’s how Joseph Siprut — lawyer, entrepreneur, producer, actor, wrestler, mixologist, bachelor extraordinaire — would like you to think of him. Kim Brooks profiles Chicago's Jay Gatsby.

2. What If Your Alderman Were Goth?

The new satirical website Chicago Genius Herald photoshopped aldermen with white makeup, black nail polish and tattoos. Turns out, it’s a great way to find out who represents you on the City Council.

3. Steve Easterbrook Wants McDonald’s to Think Like Silicon Valley

Online delivery. Mobile phone chargers. Order kiosks. McDonald’s CEO really wants Millennials to eat Big Macs. Bloomberg Businessweek asks whether the company can adapt to the 2020s.

4. Austin, Say Cheese!

Alt Space Chicago took professional portraits of Austin residents to display around the neighborhood. The photographers wanted to depict Austin “in a different light” than most media portrayals, they told the Austin Weekly News.

5. 31 Guys, 31 Teams: Your 2019–20 NHL Preview

Patrick Kane, Jonathan Toews, and Alex DeBrincat can score. The Blackhawks’ terrible D — second in shots allowed — is the reason they’ve missed the playoffs two straight seasons. Deadspin relegates the Hawks to “Weirdos and Wackjobs,” its category for the league’s mediocrities.

6. What’s the Public Appetite for a Chicago Teachers Strike?

Parents are supportive of the Chicago Teachers Union, especially on the South and West sides — but not as supportive as when the union took on Rahm Emanuel in 2012. WBEZ education reporter Adriana Cardona-Maguigad has the lowdown on the city’s pre-strike mood.

7. Victory! The Right to Bike on the Riverwalk Is Preserved. Now About Those “No Biking” Signs.

Ald. Brendan Reilly never followed through with his proposal to prohibit cycling on the Riverwalk. Streetsblog Chicago is taking a lot of credit for defeating a ban.

8. Lightfoot’s About to Enter the Toughest Two Weeks of Her Career.

Battling the teachers union for control of the schools and passing a budget that begins the task of closing an $838 million deficit could determine success or failure for the new mayor. Greg Hinz of Crain’s Chicago Business explains what’s at stake.

9. ‘A Place of Refuge’: Bird-Watching Takes Place on Chicago’s South Side

Fifteen years ago, Sherry Williams started “Afrobirding” tours at sanctuaries she created in Pullman and at Stephen Douglas’s tomb. The “invisible church” of nature can be found even in the city, she tells the Christian Science Monitor.

10. Chicago Bulls: 3 Realistic Expectations for Denzel Valentine in 2019–20 Season

After missing all of last season with an ankle injury, Valentine needs to improve his mobility, hit 40 percent of three pointers, and get more minutes off the bench. As #2 shooting guard, “the health and production of Valentine [is] absolutely crucial,” says Bulls blog Pippen Ain’t Easy.