Who was Chicago’s Best Mayor?

Who was Chicago’s Best Mayor?

Who was Chicago’s Best Mayor?

With Mayor Rahm Emanuel bowing out of next Spring’s Chicago mayoral elections, it’s a good time to look at the past eight of Chicago’s mayors to decide who was the “best” in a lot of different categories including inspirational, vindictive, vision, historic, and most productive.

By Ray Hanania

Ray HananiaChicago Mayor Rahm Emanuel’s decision not to run for re-election shows that despite his problems, he’s not all bad. A terrible mayor, he at least decided to give the citizens a break. But who is the “best mayor?”

Emanuel leaves Chicago with his tail between his legs, as one of the worst mayor’s Chicago has ever had. And I know, because I have covered them all.

Emanuel leaves Chicago politics in a mess, and a city savaged by uncontrolled street gang gun violence. He was unable and incapable of coming up with a solution. He blew his chance to help Chicago; his only contribution is his decision to not run.

There are a lot of ways to rank Chicago’s mayors. Who inspired the public the most? Who was the most vindictive? Who was the most historic? Who had the greatest vision for the city? And finally, who achieved the most?



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I covered seven of the past eight mayors – if you can include David Orr as a “mayor.” He really wasn’t much of a mayor at all, just an ego maniac who wanted recognition.

Inspirational: I put Jane M. Byrne at the top having inspired the most enthusiasm and promise. Byrne’s election made voters believe in the unbelievable, that a Chicago mayor could put the voters above a mayor’s family and cronies. Harold Washington also inspired many people to “believe,” but mostly the African American community. Washington failed to sell his vision to Chicago’s non-Black citizens.

Vindictive: When it came to vindictiveness, Byrne was far from the worst. The worst was Richard M. Daley, who based the entirety of 22-year years in office on “getting even.” What kept Daley in office as Chicago’s longest serving Chief Executive, 22 years? Well, in all honesty, it was public exhaustion. The racial strife of the Byrne and Washington years squeezed the life out of the public’s will to live. We turned away from reform and re-installed a new dictator into office because we just couldn’t face the nerve-racking uncertainty. But Daley couldn’t get past his hatred of Byrne.

Vision: Richard J. Daley, the Boss, and Byrne are tied for this one. Daley envisioned a Machine that could provide the basic essentials to the public while providing the more lucrative essentials to his friends, family and cronies. Byrne inspired us with promises that were, initially, amazing, including her biggest contribution which wasn’t to enliven Chicago with festivals and celebrations, but by creating the Neighborhood Department headed by the late Harry Sikorski, a true visionary himself.

Historic: Byrne and Washington shattered glass ceilings, as the first woman mayor and the first African American mayor. Although Bilandic once compared himself to Jesus Christ, Richie Daley came closest when Washington’s death resurrected his aspirations to dynastic achievement.

Who did the most for Chicago? That’s a tough one. Michael A. Bilandic was a brilliant numbers guy and could manage budgets, but he just didn’t know how to deal with people. Of course, anyone following in the footsteps of Chicago’s first real Boss would never live up to expectations. Byrne got a boost as a woman, and Washington got a boost as a Black. Eugene Sawyer’s legacy is as wobbly as were his knees when he had to be held up to succeed Washington in 1987 and did little than hold the seat for Boss II.

Unfortunately, the “Bosses” son Richie just couldn’t handle Byrne holding an office all of his cronies said belonged to him by birthright. Daley II did everything possible to block her programs. Byrne revitalized Navy Pier, State Street and brought life to the neighborhoods and she did it all in under 4 years. Daley was in office 22 years and what did he really do?

I have to give it to Jane Byrne. Street gangs thrive on the fear of the people in the neighborhoods and they worsen as the public hides in their homes. Byrne did everything to bring the people out by reversing herself on ChicagoFest, launching Taste of Chicago, and creating neighborhood festivals and celebrations.

So, I rank the mayors in this order: Jane Byrne, Richard J. Daley, Harold Washington, Michael A. Bilandic, Eugene Sawyer, Richard M. Daley, David Orr, and Rahm Emanuel.

In the end, I couldn’t really think of one thing that Emanuel did right.

(Ray Hanania is an award-winning former Chicago City Hall reporter and columnist. You can reach him at his personal website at www.Hanania.com or by email at rghanania@gmail.com.)


Ray Hanania

Ray Hanania is an award-winning columnist, author & former Chicago City Hall reporter (1977-1992). A veteran who served during the Vietnam War and the recipient of four SPJ Peter Lisagor Awards for column writing, Hanania writes weekly opinion columns on mainstream American & Chicagoland topics for the Southwest News-Herald, Des Plaines Valley News, the Regional News, The Reporter Newspapers, and Suburban Chicagoland.  

Hanania also writes about Middle East issues for the Arab News, and The Arab Daily News criticizing government policies in the Israeli-Palestinian conflict.

A critic of mainstream news media bias, Hanania advocates for peace & justice for Israel & Palestine, & the empowerment of Arabs in America. 

"I write about three topics, the Middle East, politics and life in general. I often take my life experiences and offer them in an entertaining way to readers, and I take on the toughest topics like the Israel-Palestine conflict and don't pull any punches about what I feel is fair. But, my priority is always about writing the good story."

Click Here to LISTEN to Hanania's live radio show on 2nd Friday every month 7 AM CST. Click here to listen to Ray's Podcasts. 

His columns are archived here. Hanania was named "Best Ethnic American Columnist" by the New America Media in November 2007, and is the 2009 recipient of the SPJ National Sigma Delta Chi Award for column writing.

Email Ray Hanania at rghanania@gmail.com.

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