It's a tall order: write objectively about your billionaire boss who's also mayor of the city you live in.
That's the challenge faced by Henry Goldman, who has covered Mayor Bloomberg for Bloomberg News since 2001.
Mr. Goldman's job is inherently problematic: cover the mayor too positively and risk looking like a shill; cover the mayor too negatively and risk the ire of the man who pays his salary.
"I can't think of a more uncomfortable position to be in," said Joyce Purnick, the author of "Mike Bloomberg: Money, Power, Politics" and a former City Hall bureau chief for The New York Times. "I'm not suggesting any direct pressure to write a certain way or cover something or not cover something or ask something or not ask something. I don't think Henry would put up with that. But the pressure to just stand up straight and keep things objective -- it's just got to be very, very difficult. I don't know how he does it."
"The reporters and the editors know where they can't go," Purnick said about Bloomberg News in general. "There are just certain things you don't cover. You're not going to do a major investigative story that would rebound negatively on the administration. You cover the news and you don't do major potentially negative enterprise pieces."
In March, Editor & Publisher criticized Bloomberg News' coverage of last year's snow storm writing that the news agency "totally ignored the intense debate over the mayor's whereabouts as 20 inches of snow closed in on New York."
The news service behaved as if City Hall had sent over a city editor to make certain the majority owner of its company wouldn't get into trouble during any of his snow days. Like a parent protecting his delinquent child.
The mayor was roundly criticized for his handling of the December blizzard.
But reporters who spoke with the Times described Goldman's reporting as fair and objective. They also said he did not appear to receive preferential treatment from the mayor.
Earlier this month, Goldman covered former Schools Chancellor Cathie Black's abysmal approval ratings, letting the numbers speak for themselves:
Cathie Black, the former Hearst Magazines chairman chosen by New York Mayor Michael Bloomberg as schools chancellor last year, holds a 17 percent approval rating among city residents, a Marist College poll found.
The survey showed that only 2 percent rate Black’s job performance as “excellent,” while 15 percent grade her as “good.” Among the rest, 34 percent rate her “fair,” 27 percent “poor” and 23 percent reserved opinion. Black got a 21 percent approval rating in February, the poll said.
The New York Observer finds itself in a similarly prickly position. The paper is published by Trump's son-in-law, Jared Kushner. Gawker recently accused the Observer of suffering from a willfull Trump blindness, but lately the Observer's coverage of Trump's presidential run has not shied away from his controversial birther statements or his bizarre notes to media outlets who he feels cover him unfavorably.
The Observer's Peter Feld explains Trump's appeal to Republicans thusly:
Trump, the Pet Rock of 2012, merges two major trends of this year's motley Republican crop: cartoonish, shoot-from-the-lip attacks on Obama (like Michelle Bachmann, Newt Gingrich and Sarah Palin) and television celebrity (Palin again, and Mike Huckabee). Although Trump's political support seems premised on his celebrity as a businessman and "boss," he has tried to build a political foundation on his balls-out willingness to gleefully flaunt the Birther attack on Obama--avoided by most of the mainstream candidates--seizing (literally) what marketers call "the white space," and making himself for now the plurality pick of Tea Partiers.