Last fall, after Chicago’s bid to host the 2016 Olympics went south (all the way to Rio), reporters asked Mayor Richard M. Daley if he would seek a seventh term. “I don’t know why you already put me in the grave,” he replied.

Winning an election is never a foregone conclusion, not even if your name is Daley, and the mayor’s current approval ratings—his lowest ever—don’t promise a cakewalk.

He is expected to announce his intentions soon (the primary is February 22nd). There are a few whispers that he won’t run—that he is content to eclipse his father’s record tenure of 21 years as Chicago mayor, a milestone he’ll reach in December, and that he worries about his wife, Maggie, whose health has suffered since she was diagnosed with breast cancer in 2002.

But if Daley runs and wins in 2011—and the odds are he’ll do both—it would likely be his last term (he’d be 73 at the end of it, in 2015). If so, he could indulge in that rarest of political gifts: the freedom to make difficult, even unpopular, decisions for the long-term good of the city, without concern for how he’d weather the political fallout.

With that in mind, we have compiled a mayoral to-do list that would impress even Daniel “Make No Little Plans” Burnham. In it we have incorporated ideas from politicians, pundits, civic leaders, and academics. The dozen or so we spoke to all think Daley will run, and some doubt he will exit the stage even in 2015. Should Daley bow out (as his brother Bill recently speculated), our list offers a plan of action for Chicago’s new chief executive.

Can the mayor, a child of patronage, actually reduce the size of city government and make Chicago more efficient? Can he muster an Olympic-size effort to combat poverty and violence? Will he finally gamble on a casino? Everyone has an opinion, though it’s a testament to Daley’s hold on power that many chose not to share theirs publicly.

You’ll no doubt have your own list, and we invite you to submit ideas and vote for your favorite here.

Our list is by no means comprehensive. Some items require money—and lots of it—a commodity already in short supply. A few ideas would burnish the mayor’s already considerable legacy, while others would nudge him beyond his comfort zone. One or two may simply be pie in the sky.

But as Burnham once said, “Aim high in hope and work, remembering that a noble, logical diagram once recorded will never die. . . . Think big.” (Actually, no one knows if Burnham really said that. But it’s a bit more positive than the old Chicago ward committeeman’s gem: “We don’t want nobody nobody sent.”)

So please don’t take this the wrong way, Mr. Mayor. We give you your Bucket List: ten big things to do for Chicago before you leave office. No actual bucket kicking implied.

1. Enough with the patronage already

We might as well start here. Clout and cronyism are part of Mayor Daley’s genetic code. But that may also make him the only person who can actually change the way Chicago works. Or in this case, doesn’t work.

Michael Shakman, an attorney whose name is synonymous with the 40-plus-year struggle to end patronage, thinks the city is making progress, with a federal monitor to watch over hiring and an inspector general with real power to investigate corruption.

What remain are a few patronage loopholes big enough to drive a hired truck through. For example, the mayor should extend the city’s do-not-rehire list, which bans city workers fired for wrongdoing from future employment, so that it applies to sister agencies, including the public schools, the Chicago Park District, and the Chicago Transit Authority, where far too many banished city workers have been sent to live out their golden years.

The city council needs to adopt the do-not-rehire list as well, and Daley should demand that aldermen reconsider the decision to create their own watered-down inspector general’s office. Shakman and Noelle C. Brennan, the federal monitor, oppose a separate council inspector general, citing patronage abuses that overlap the executive and legislative branches.

But the hardest part for Daley will be convincing Chicagoans that he truly is committed to ending patronage, not just federal oversight. “He needs to be an enthusiastic supporter of this, but he’s not,” Shakman says. “The city’s middle managers [still] assume that patronage was how they advanced, and they haven’t gotten a strong sense from the mayor that it should be any other way.”

Here’s his chance to send a signal.

2. Reduce the size of government

Ending patronage and cronyism isn’t just about politics or even ethics. It’s about reality: Patronage no longer pays. We simply can’t afford it. City government can operate with fewer people, not by eliminating the men and women who actually do the work—police, firefighters, inspectors, and the like—but by reducing the number of supervisors, deputy commissioners, and assistant whatevers who have long puffed up the city’s payroll and pension obligations and who got there because of clout. (Eleven years ago, the Chicago Tribune documented 68 members of the Daley clan on various public payrolls.)

Daley prides himself on being a modern urban executive, but the city still operates with an outmoded, inefficient, top-heavy management style. Excluding the police and fire departments and the city council, City Hall employs about one manager for every eight workers, and many of those positions are where patronage lives. Managers’ salaries total about $175 million a year; reducing that payroll to a more contemporary private-sector ratio of one manager for every ten or twelve workers could save up to $50 million in annual salaries and millions more in pension payments.

In June, Daley proposed outsourcing some of the city’s hiring practices to remove the taint of patronage. Here’s a better idea: Bring in an outside expert to eliminate some of the waste and overlap in Cook County’s nearly 500 units of government. Do we really need a city and a county election board or two health departments? Public officials never want to give up their fiefdoms, but Daley, unburdened by such parochial considerations, could lead by his willingness to give something up—and in the process save millions that could be spent on vital services.

Illustration: Chris Lyons

3. Roll the dice at McCormick Place

Ending patronage and cutting waste isn’t particularly fun, so let’s do something that is: put a casino and big-time entertainment complex in the Lakeside Center, the oldest McCormick Place structure and a building that has outlived its usefulness as a trade show venue.

The Metropolitan Pier and Exposition Authority, known as McPier, is in the toilet, and the reasons are many: too much patronage, questionable contracts, unwieldy union work rules, and fierce competition from Orlando and Las Vegas, which provide far greater subsidies to their convention centers. Given the miserable state of Illinois’s finances, we can’t count on more sales taxes to bail out a convention business that everyone agrees is critical to the city’s economy.

Even with all the problems at McCormick Place, conventioneers still want to come to town. Chicago is located in the center of the country, with great shopping, restaurants, and nightlife. The newer McCormick Place buildings are spacious, modern, and beautiful. Add a casino and some top-line performers and you’re back in business.

Daley has flirted with casinos since taking office in 1989. His last proposal, in 2004, called for a casino that would generate up to $700 million a year in state tax revenues and another $300 million for local governments.

The moral arguments against gambling? Puh-leeze. We’re surrounded by casinos, racetracks, off-track betting parlors, 9,000 different lottery games, and now, perhaps, video poker at your local saloon. Can we get a gaming license through the Illinois General Assembly? The state is broke, and the leaders of both houses are Chicagoans. What’s the point of being the Cloutmeister if you can’t get a no-brainer like this done?

The big casino operators will pay handsomely for the privilege. This ain’t no parking meter giveaway; this is the deal that keeps on dealing. Hire experts to run the place and give the city a healthy cut. Employ Chicagoans to build the damn thing and work there. And watch the Near South Side prosper, the trade shows flock back to Chicago, and the tax money roll in.

4. Make Chicago a mecca for same-sex marriage

Deb Mell, a state representative, says she has to leave Chicago and go to Iowa to get married. Really? Iowa is the farm team. Just because Mell is Patti Blagojevich’s sister is no reason to make her go into exile to get hitched.

This is a mayoral slam dunk. “Rich Daley is the poster boy for the gay rights community,” says Rick Garcia, political director for Equality Illinois, an advocacy group for gay, lesbian, bisexual, and transgender people. “He’s the mayor of America’s major city. He’s Irish, he’s Catholic, and he has influence all over the country. This is real to him. It’s about protecting families.”

The state decides marriage law, but counties issue licenses. Six years ago, Daley said he was all for Cook County handing out marriage licenses to same-sex couples, and the county clerk, David Orr, said he was game to try it. So let’s go. (Officially, Orr will be committing a misdemeanor, Garcia says, so it would be nice if the mayor paid Orr’s fines.)

The country is fast coming around on this, and so is our state. In 2004, a Copley News Service poll found that more than three-quarters of Illinoisans supported either same-sex marriage or civil unions. The Illinois House legalized civil unions last year, but the bill is stalled in the state senate.

That’s not good enough. By their actions, Daley and Orr can push the Illinois legislature to pass what many consider a basic civil right protected by the U.S. Constitution.

Just think: Couples would flock to Chicago to get married. And who knows? Maybe they’d settle here, raise families, pay taxes, and contribute to the city’s vibrant civic and cultural life. Besides, Chicago is a great place for a honeymoon. After getting married, the newlyweds could take in a show and hit the tables down at McCormick Place.

Cha-ching!

5. Take a hammer to that TIF piggy bank

Ben Joravsky and Mick Dumke of the Chicago Reader have done the heavy lifting on this subject. Tax Increment Financing (TIF) districts throw about $500 million a year into a special fund controlled largely by the mayor. In TIF districts, property tax revenue that would normally go to the city, the schools, and the other taxing bodies is frozen. When TIF properties increase in value, the extra tax revenue they generate goes into the pot for improvement projects.

The TIF fund was intended for the development of blighted neighborhoods, but over the years it has devolved into a kind of mayoral secret stash kept off the budget books, with much of the money paid out to clout-connected developers and big corporations for special projects. The Reader stated that at the start of 2009, the city had more than $1 billion available in the TIF fund.

TIFs are among the mayor’s favorite things, so letting go won’t be easy. Scott Waguespack, the 32nd Ward alderman who cosponsored last year’s ordinance that will begin to put TIF documents online, wants the city to suspend current TIF spending and use that money to address critical issues, including schools, housing, and parks.

“We’re in a crisis here, and we don’t even know how much money is out there,” Waguespack says. “We need to find out what’s been committed and what’s available and review how we might use some of that money now. Then we’ve got to change the TIF guidelines to get the program back to its original intent.”

And dipping into the TIF fund now isn’t like selling a valuable asset and then using half the money to plug one year’s budget gap, as the city did by privatizing the Skyway, Waguespack says. This is money that government already had coming, and TIFs can continue to generate development funds for years to come.

6. Use some TIF money to push school reform

In the mad scramble for TIF cash, first in line should be the public schools, which last year alone would have received an additional $250 million had the property tax revenue not been diverted by TIFs. Daley could use that money to solve one of the thorniest school reform issues: teacher evaluation.

One of the biggest variables affecting student achievement is teacher quality, but the school board does a lousy job of identifying bad teachers, and the Chicago Teachers Union resists any attempt to eliminate job security based on seniority.

Daley should recruit the union to play a bigger role in teacher evaluation. A recent pilot program in 44 Chicago elementary schools found that veteran teachers were the toughest evaluators of talent, rating 8 percent of new nontenured teachers unsatisfactory—much higher than the 0.3 percent of Chicago teachers who get bounced under the board’s current system.

The union would have to give up some of its seniority protections, but in return it would get improved professional development for teachers who need it, paid for in part with TIF funding. In short, teachers would get better job security because they would become better teachers.

Getting the union to commit to a good evaluation system that gets rid of bad teachers but changes the schools’ approach to professional development would be a worthy accomplishment, says Linda Lenz, founder and publisher of Catalyst Chicago, an independent newsmagazine on school reform.

“Paying people because they got another degree doesn’t have any impact whatsoever on student achievement,” Lenz says. “The whole school educates kids. Take that money and use it to develop teachers and everyone else in the school, to deliver for the kids.”

7. Make Chicago the greenest city in the United States

In February 2008, Popular Science magazine deemed Chicago the ninth greenest city in the United States. Not bad, but let’s go for number one.

This one is right in Daley’s wheelhouse. He plants trees and green rooftops to combat air pollution, advocates solar and wind power, and pushes for significantly reducing energy and water consumption in new and retrofitted buildings.

Yet for all his street cred, the mayor still has a real blind spot when it comes to recycling. Remember the blue bag program? Neither does anyone else. We were supposed to use the bags to separate our recyclables, but few of us did, and the program was marred by charges of contract cronyism and inflated estimates of its success.

It took a while, but Daley finally gave up on blue bags, and now we have blue carts that allow residents to put recyclables in a special bin picked up in a separate garbage run. It’s a much better approach. But only 26 wards have blue carts, and the mayor says the city can’t afford to extend the program to the others. Once again, that TIF fund might come in handy to get the program to all 50 wards and sell Chicagoans on the idea. Daley could create additional savings by eliminating the longstanding (and patronage-tainted) practice of three-person garbage trucks (two workers are plenty) and replacing ward-by-ward pickup with a more efficient grid system.

8. Trains, not planes or automobiles

Chicago won’t be truly green until people—politicians included—change the way they think about public transit. Too often, this debate gets characterized as Chicago versus downstate or the city versus the suburbs.

That’s so last century, says Frank Beal, executive director of Chicago Metropolis 2020, a regional planning group. More than a quarter of Chicago Transit Authority riders live in the suburbs, and 36 percent of the ridership of PACE suburban buses is Chicagoans. “That’s the problem with transit,” he says. “The agencies don’t speak with one voice, and, more important, they don’t have a dedicated source of funding.”

First up for the mayor: Lead the charge to consolidate the four transit boards that govern metropolitan transit into one. Combined, the CTA, Metra, Pace, and the Regional Transportation Authority have 47 board members and spend millions on overlapping administrative costs. The agencies can demonstrate their commitment to further cost savings by issuing a single fare card that can be used on any system.

This will take state legislation, but Daley can step up by using the bully pulpit of his office, aligning himself with suburban leaders, and releasing some control over city transit. And while he’s at it, he can give his allies political cover by advocating the unpopular but necessary step of adding a six-county surcharge to the gas tax dedicated to public transit.

Daley can do for transportation what he did for public housing, Beal says. “We can argue about the execution of the details and the timetable, but the mayor saw a major problem, recognized a completely dysfunctional system, went to the feds for help, and got it,” he explains. “We need to do the same thing for our regional transit system.”

9. Turn Olympic dreams into safe streets

The best thing to come out of the Olympic debacle was that it demonstrated how the city—government, residents, businesses, and civic leaders—could rally around a common purpose. Just because we didn’t win the bid is no reason to let all that goodwill fade away. We need an Olympic-size effort to combat the two issues that keep Chicago from true greatness: poverty and its evil twin, crime.

The mayor boasted he would raise $246 million for the Olympics from private donors, including businesses and foundations. Even a fraction of that would help us stop children from being killed or going to bed hungry.

It’s high time we made this a priority, but the city clearly doesn’t have the resources to hire a thousand more police officers or fund a summer jobs program. Cynics will say that all those influential types got behind the Olympic bid only because of a famous Chicago aphorism: “Where’s mine?” The games promised contracts, jobs, business, and development opportunities—clout central. It’s up to the mayor to demonstrate that real dividends come to businesses that help make Chicago a better-educated, safer, and more livable city.

“I think there’s great opportunity to mobilize that same passion and effort and direct it at these issues,” says David Hiller, the president and chief executive officer of the McCormick Foundation. “High on the list would be a concentrated effort to make the city safe and secure, particularly for our children. In a world-class city like Chicago, this [level of violence] should be unacceptable.”

An Olympics-style campaign would make these issues more visible, Hiller adds. “There are thousands of great efforts going on out there. We need a center of gravity to pull these things together.”

The Olympics would have been the capstone to Mayor Daley’s career. This would be a public-private partnership far more worthy of his legacy.

10. Impose term limits on the mayor’s office and the city council

We’ll end where we began: If Chicago is really ready for reform, Daley can take a monumental leap forward by championing term limits—for his office and for aldermen.

“Mayors tend to be more dictatorial the longer they’re in office,” says Dick Simpson, the former 44th Ward alderman and longtime professor at the University of Illinois-Chicago. As for the aldermen, they have presented us with overwhelming evidence for term limits: They get indicted and convicted at the rate of almost one per year.

Sure, some people will argue that term limits deny the council valuable expertise on vital city issues—but the people who argue that are already aldermen. To win council approval, the mayor should give up his power to fill aldermanic vacancies. Daley has appointed 35 council members in two decades. Ward residents should choose their own representatives; when aldermen die or resign with more than a year left in their terms, let’s hold a special election to find their replacements.

Most term limits are for two four-year terms, but even three terms would be OK, Simpson says. Even then, aldermen are likely to balk at the change, and when that happens, the mayor should take this measure directly to the voters. New York City imposed two-term limits on council members in a 1993 referendum. In 2008, the New York City Council voted 29–22 to keep the limitation but extend it to three terms.

Some will complain that in this scenario Mayor Daley gets to have it both ways: After ruling Chicago for 25 years, he will single-handedly deny anyone else the chance.

True enough. But that could turn out to be clout’s finest hour.