May We Car-Pool? Wed at Macy’s? It’s Up to the Conflicts Board

She pocketed a $3.3 million retirement package when she left I.B.M.’s board to assume the helm of New York City’s public schools in January.

But when the company then wanted to present Cathleen P. Black with a heavily engraved silver tray as a further token of its esteem, the new chancellor trod carefully: inquiries were made to see if she could accept the gratuity in light of the city’s ban on gifts worth $50 or more.

These are the questions that confront the city’s Conflicts of Interest Board at least 500 times a year. Fielding inquiries from city employees in need of guidance, the board’s legal arbiters consult the city charter. When requests are modest — say, someone hoping to moonlight as an emergency medical technician — approval can be swift.

But some requests are outsize enough to make the supplicants sound like indulged children begging Santa to lasso the moon. Take the plea of a police officer offered an all-expense paid wedding by Macy’s. In a surprising act of leniency, the board ruled that he could accept the $25,000 package, an amount that “would clearly violate” the charter absent board permission, on the condition that he no longer patrol the area around Macy’s flagship store in Herald Square.

Rejections are not made public. But when the board issues a waiver to permit conduct that would otherwise be barred by the law, as it did for Ms. Black, the notification letter becomes a public record.

This occurs just over 200 times a year, judging from the three-ring binders where the board keeps letters spanning the last 15 years. Safeguarded in an office that visitors cannot enter without being buzzed in, the binders’ thick contents, which City Room readers can sample here, provide an illuminating peek into the lives of public servants at all levels of city government from cosseted commissioners to custodians who clean up after them.

There’s Police Commissioner Raymond W. Kelly, who received permission recently for a lieutenant to moonlight as a limousine driver in his spare time.

Adrian Benepe, the parks commissioner, went to bat for John Herrold, a senior administrator at Riverside Park, who wanted to collect $48,000 a year in supplemental pay — more than half his city-issued salary — from the Riverside Park Fund, a nonprofit group that he has helped raise money to support the park.

In February, a top official at Bellevue Hospital Center and another employee who reports directly to him jumped through hoops to make sure they could car-pool without running afoul violating city prohibitions on financial dealings between bosses and subordinates. Simply maintaining that their plan would trim their commuting costs and “help preserve the environment” failed to sway the board, which approved the arrangement only after the workers insisted it was voluntary and the two pledged to split the driving and expenses.

Before their case is reviewed by the five-person conflicts board, city workers seeking waivers must have the support of the agency where they work. For employees considering outside jobs, that approval is easier to come by when the outside job is far afield from their official duties.

That explains how Ron Douglass, an administrator in the city’s finance department, got a green light to appear on NBC’s “Saturday Night Live” and in horror films, both of which have the virtue of shooting scenes at night. (“It was one night and one weekend,” Mr. Douglas said of his 2006 appearance as Charles the Waiter in “Zombies Anonymous.”)

It also explains how Robert Richardson, the director of a 14-person Correspondence Unit that responds to letters, e-mails and 311 calls addressed to Mayor Michael R. Bloomberg, was allowed to teach a course at Cooper Union focused on Wittgenstein, the Austrian philosopher.

And it explains how Calvin M. Yee, a tech support specialist, spends Monday nights teaching ballroom dance to older people in Lower Manhattan. He was recently directing six couples on the finer points of the tango, calling out, “Man. Man. Kuai, kuai, man,” followed by “Slow. Slow. Quick, quick, slow,” for the lone dancer who does not speak Mandarin.

Mr. Yee said he understood why the city expected him to get a waiver. “You have all these companies that want to get their foot in the door” of the officials who control government purse strings, he said.

“Dancing is never going to affect any of my computer decisions,’’ he said.

Though the letters reflect some board appears to be rigorous in its deliberations, a handful of some decisions might raise eyebrows among good government advocates.

For instance, the board allowed two city employees who had been asked by a commercial publisher to write an engineering textbook to be paid for their time. But nowhere do the notification letters address the propriety of marketing the $61 book, as the publisher expressed interest in doing, to the authors’ own students at New York City College of Technology. Because City Tech and other City University of New York campuses are technically state operated — despite their names — the board apparently takes the view that acts that sully the university’s reputation are not the city’s problem.

Equally hard to reconcile, in light of the stiff rebukes handed out by the board when public servants accept gratuities as trifling as free popcorn, was the five-page ruling issued in February allowing the police officer to have his wedding financed by Macy’s.

According to the notification letter, the officer, Moise Naolo, who is assigned to Midtown South, fell hard for a tourist who was admiring Macy’s windows during its annual flower show. The following year, the patrolman persuaded Macy’s to let him put a marriage proposal in the window near their meeting spot. Hearing that his proposal had been accepted, the store offered to hold the wedding at this year’s flower show. The $25,000 soup-to-nuts package included a bridal gown, tuxedo, mother-of-the-bride dress, catered food for 100 plus cake, rings and flowers.

The board held its peace and allowed the nuptials to proceed, steps from the handbag department. It merely asked that Officer Naolo transfer to a new precinct and that Macy’s refrain from publicizing his former beat in Herald Square. Asked why the board pressed to keep that fact under wraps, a lawyer for the board would not elaborate.

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