A senior City Hall aide describes one meeting with a group of out-of-town businessmen who thought they had curried favor by speeding along a project at the mayor's request. "They were trying to get some concessions from the city on a deal," the aide recalls. "At one point, their main negotiator said, 'We did this for him, so we expected you would reciprocate.' All the guys from our side of the table got really quiet. It was like a mask had come down over their faces. We just stopped reacting." The deal, naturally, went nowhere. 

Demanding repayment sends the signal that you treat your favors like accounts receivable--a fatal breach of etiquette. Scott Hodes likens favors to unenforceable promissory notes, explaining, "Most people would say 'Fuck you' if you demanded payback." Chicago Tribune writer Mike Conklin--who did a constant business in favors during his five years on the paper's "INC." column--remembers sources who actually tried this tactic. "Once someone said, 'You owe me,' that was it for them," he explains. "Maybe that time I'd do what they were asking. But I'd never return their calls again."

Why does the idea of demanding payback ignite such contempt? "People who keep score are perceived as being in the short-term game," says Tom Doody. "I just disengage from them." That's the strategic explanation, but there's an emotional angle as well: Whatever their other motivations, people who do favors feel good about themselves afterwards. "If you do a favor for me, it's supposed to be because you're a great guy," says one veteran Democratic operative. "So when someone tries to call in a favor like they're a bill collector, it makes the whole relationship null and void." Demanding repayment, in other words, rips down the façade of altruism that cloaks so much of the favor economy's dealings. And, really, who wants to feel like a glorified precinct captain?

But if demanding repayment is taboo, how do players cash in old chits? Many start by simply describing the issue at hand to a person they have helped in the past, perhaps even invoking that previous favor in a nostalgic way. This lets the person know, indirectly, that this would be a great chance to return the favor. Usually that suffices. If not, it may be hopeless. "If someone doesn't understand that they owe you," says Serafin, "nothing you say can make them get it."

Corollary to Rule 5: You can demand repayment for granting a favor, but only if you do so immediately.

When White Sox owner Jerry Reinsdorf asked public relations executive Kathy Posner to fill in for him as Principal for a Day at Doolittle East Middle School, near Comiskey Park, she had an immediate request: that the Sox furnish a memento for every student, and that she get to throw out the first pitch at a Sox game. On June 16th, Posner launched a slider from the pitcher's mound at Comiskey Park before more than 10,000 fans--all of whom, she admits, "probably wondered, 'Why is she there?'" A crew from Dateline NBC even taped the moment, to be used in a segment profiling her as the archetypal workaholic. As Posner explains all this to me, I glance up and notice a sign on her office door. It reads, "What's the half-life of a favor?"
  Rule 6: Always try to offer a favor before it is requested.

Again, feelings matter in the favor economy, and a favor offered voluntarily pads the offerer's account in several ways. He or she gets credit not only for the favor itself, but also for having spotted a need and filled it unprompted, the mark of a real friend. 

What's more, the recipient is doubly grateful--for the favor, of course, but also for having been saved from pleading. "It's always better if you don't make people ask," says Maureen Smith. "If you know someone's child is applying to your alma mater, you offer to write them a recommendation letter."

Smith recalls that when she moved to Chicago from New York after marrying E. B. Smith, the Chicago banking scion, a great many people volunteered to help introduce her around--offering everything from seats on charity boards to invitations to society lunches. "I will forever be grateful to those people," Smith says. "Though I have to admit, at first that style of doing things made me a little paranoid."

Of course, being in a position to offer unrequested favors projects an image of power and connections. "For some guys, doing favors for people is almost like a show of plumage," says Tom Doody. In the world of politics, this can have amusing effects, as officials scramble like claim jumpers to take credit for a favor--say, the securing of a zoning variance--for which they had marginal responsibility.
  Rule 7: Those who abuse the system get frozen out.

Though Carol Moseley-Braun's political demise last year had many causes, her failure to play the favor game correctly hardly helped. Fundraisers regularly complained that the senator showed up late to their functions and often didn't work the room hard enough. By the time her campaign needed money to fight her opponent, Peter Fitzgerald, heir to a banking fortune, the damage was done. Just before the November election, one Democratic operative told me, "If I've heard it once, I've heard it ten times: Major Democratic women fundraisers are complaining that they haven't heard from her since '92." 

Thus, though senators wield a fair amount of clout, many Democratic insiders didn't go out of their way to help her, figuring their hard work would go unremembered--even in the unlikely event that she beat Fitzgerald. (Confirming her status in some people's eyes as only a "taker" in the favor economy, the defeated Moseley-Braun never endorsed Mayor Daley during last winter's municipal election--even though Hizzoner had thrown the senator a half-million-dollar fundraiser during her re-election campaign.)

Things can turn equally frosty on the social front. Maureen Smith recalls the case of one CEO who had recently arrived in Chicago and seemed poised to slide seamlessly into the city's high society. Then came an important Christmas party, the sort of elegant event at which merely being invited counts as an honor. The CEO "showed up in a horribly casual outfit, and spent the evening telling people exactly how unsophisticated he found Lake Forest, compared to his East Coast hometown," Smith recalls. "Then he bragged about how someone was 'begging' him to join the board of an important downtown arts institution. He didn't know it, but the head of the organization's board was sitting at his table. I never saw him at another party." 

As in any market, the trade in favors fluctuates in value. Here's an index of those that have spiked up or down lately.

Chicago Bulls tickets: Hundreds of thousands of Chicagoans had forgotten how tedious a pro basketball game could get, even with inane contests and routines filling every spare second. 
Forecast: Decline may have bottomed out, but no signs of a rebound yet.

Cuban cigars: When the big boys play at being bad boys, the "Cubans" come out. Now that the cigar craze is leveling off and even your accountant claims a direct pipeline to Havana, the major players compete to pass out the rarest among the Cuban brands.
Forecast: Stable, with slow growth, at least until Fidel Castro dies or the embargo gets lifted.

Hotel rooms: Chicago's convention business can make it a tough place to score a room on short notice. But a few real estate bigwigs and PR types have hotel connections, and their out-of-town friends appreciate not having to choose between the far suburbs and a downtown fleabag.
Forecast: Slight downturn possible, due to the recent flurry of hotel construction.

Jerry Springer tickets: Critics may call the show a moronic slugfest, but it's still a favorite favor. "You wouldn't believe what Springer tickets can do," says Kathy Posner, whose access to tickets stems from her days as Springer's flack. "I have been hit up by friends, clients, their relatives, and even White Sox players."
Forecast: Springer's distributors claim they will no longer air violent incidents, so the show's cachet may dim. Then again, sitting in the audience might become the only way to see the unedited mayhem.

Charity board seats: Corporate flight and a general decline in civic-mindedness have created high turnover in this sector. As Maureen Smith points out, "There are more seats now, but less longevity," so the chance of rubbing elbows with a true heavy hitter has faded somewhat. 
Forecast: Continued decline, unless a new civic spirit captures the city's upper crust--and business leaders stop losing their jobs to mergers.