Illustration by Hanoch Piven
Illustration: Hanoch Piven

After Mayor Rahm Emanuel abruptly declared the end of his reelection bid in September, he wasted no time announcing his first post–City Hall plans. Like many a beleaguered figure in transition before him, he’s — shocker! — writing a book, this one due out in 2020 and partly based on his eight years managing the country’s third-largest city.

Of course, Emanuel’s literary pursuits will take him only so far after he leaves office in May. The 58-year-old near-career politician is still ambitious, combative, and relatively young. The first time he left politics, in the late ’90s, he pursued a highbrow get-rich-quick scheme as an investment banker. And you can bet he’ll follow the money into the private sector again.

Many of his detractors see him as an unsympathetic corporatist who ignored low-income neighborhoods and failed at managing some critical city functions. But that baggage won’t burden him nearly as much in the business world. Especially when you factor in the contacts he’s accrued from his prodigious fundraising for the Democrats — along with stints in the White House (on the staffs of Clinton and Obama) and Congress.

“The success he’s had is bankable,” says Chris Mooney, professor of political science at the University of Illinois at Chicago. “He’s had problems with the Chicago public schools, but no one is going to hire him to run a school system. He’s had problems with crime, but no one is hiring him to run a police department.”

Emanuel understands the intricacies (and politics) of cobbling together funding from various sources — from the federal government to private companies — to fuel projects such as the $8.5 billion expansion of O’Hare International Airport. It’s a skill set commercial builders and developers would value. “They’ll want his views toward downtown investment or how to build a complicated mixed-use development with all the moving parts and costs,” says David Greising, CEO of the Better Government Association and a veteran business journalist.

Likewise, Emanuel could be a natural fit at a private equity firm that specializes in mergers and acquisitions. Possible destinations? A local shop like Madison Dearborn Partners, tech-oriented Kleiner Perkins on the West Coast, or an elite New York investment house with international ties, speculate executive recruiters. “Rahm’s always been a deal guy,” says Tom Gimbel, CEO of headhunter LaSalle Network. “And he doesn’t have to stay in Chicago.”

Emanuel’s background also makes him a natural candidate to become a superadviser, sitting on company boards as was the case with his predecessor, Richard M. Daley, who became a Coca-Cola Company director after leaving office. Or maybe company chiefs will approach him as a high-priced consigliere for when they get in a jam or seek to expand in or relocate to Chicago.

What placement experts — most of whom spoke only on background — don’t see: Emanuel hitching himself to a senior executive or even a CEO post. Too boring and unchallenging, they say, for someone who’s consistently juggled intense urban issues, agendas, and constituencies. “Running a major city can be more complex than running a major business,” says Rick Cobb, executive vice president at Challenger, Gray & Christmas, an outplacement and executive consulting firm.

Perhaps most telling about where he’ll veer next is where he’s been: The first time he left politics, when he leapt from the Clinton administration to the Chicago office of investment banking firm Wasserstein Perella & Co., he earned a reported $16 million in three years — mainly from helping to negotiate an $8 billion utility company merger that spawned Exelon Corporation.

Emanuel wasn’t shy then about cashing in on his vast network of contacts. He also didn’t abandon his corporate friends once he returned to public service — something that should pay off for him now, with an abundance of next-career opportunities.