The thing about emails is that they live forever -- and can come back to bite you in the rear.
Such was the case Wednesday when John Kupper, a top political advisor to Mayor Rahm Emanuel, fired off a message to Chicago Tribune reporters wherein he suggested some unflattering story ideas about Cook County Board President Toni Preckwinkle, a potential contender to run against Emanuel in 2015.
Shortly thereafter, the Tribune tattled on Kupper, prompting the veteran Democratic campaign strategist to issue an embarrassing public mea culpa.
"This morning, of my own volition and without consulting anyone, I sent what I considered a private email to a couple of Tribune reporters complaining about a story they wrote and what I believe to be generally unfair reporting about Mayor Emanuel," he said in a statement.
"I regret any discomfort that I have created for Mayor Emanuel, County Board President Preckwinkle or anyone associated with their offices," he continued, vowing: "From now on, I’ll keep my media criticisms to myself."
Kupper's offending email arrived in Tribune inboxes after the paper published a story on complaints by Troy LaRaviere -- the well-regarded principal of North Side public school Blaine Elementary -- that Emanuel squashed disagreement over his education agenda and strong-armed principals into supporting divisive decisions like shuttering nearly 50 schools last year.
LaRaviere came out swinging in a Sun-Times op-ed this past weekend, pointing a finger at Emanuel for "insulting" behavior toward CPS principals who question his policies. His personal blog has become a destination for CPS insiders to vent about problems with City Hall.
In a press conference Wednesday, the mayor said he's open to hearing principals' ideas and gripes, saying: "My attitude is, 'We want to hear about it if there are any concerns.'"
According to the Sun-Times, which ran another article on the LaRaviere-led principal rebellion, a fired-up Kupper sent the paper a email earlier this week, writing: "First, this guy got a full page in the Sun-Times on Saturday. Now, a story as well? When does he get a column?”
Kupper complained that the Sun-Times only quoted "four disgrunted principals" out of the 600-plus within the district. "My daughter’s professors at Medill would label this 'selective reporting,'" he said in his message.
The Tribune, meanwhile, theorizes that Kupper's reach-out to several of its journalists was a tactic to discourage Preckwinkle from running for mayor. During Wednesday's press conference, Emanuel waved off a question on whether the Kupper email was driven by anxiety over a showdown with Preckwinkle, whose popularity among city progressives could give the politically-and-financially connected hothead a run for his money.
"I trust her when she said multiple times she's not running. I think she's a person of her word," he said.
Preckwinkle, however, wasn't going out of her way to praise Emanuel in her appearance on WTTW's "My Chicago." Asked whether the two get along, she took a long pause and then answered: "We work together."
In response to the Trib's Kupper report, the county president's campaign consultant, Ken Snyder, sniped: "I think the mayor would serve Chicagoans a lot better if he focused less on opposition research and more on doing his job."
Let this be a teaching moment: If you're going to throw somebody under the bus on behalf of your boss, who just so happens to be the Mayor of Chicago, then you might want to clear it with him first -- especially when "oppo" tactics involve shooting angry emails to two major newspapers that have all but declared war on Emanuel.
It's a competitive media marketplace, and Kupper's botched attempts at digital damage control had the unintended effect of serving up extra e-fodder for the papers' "Rahm is losing control of the city" narrative.
In other words, think before you hit "send." (Beyonce's publicist recently learned this the hard way.)