Keith Olbermann Current TV Lawsuit Settled: Was He Improperly Terminated?

Keith Olbermann seems to be on the outs with the television industry yet again. The fiery leftist talking head settled a $50 million lawsuit against his most recent employer, Current TV, on Tuesday. He sued the progressive network over his public firing last year, one year into a five-year contract.

Keith Olbermann has been unable to land another television job since he was let go by network executives Joel Hyatt and former Vice President Al Gore. He has used the subject of his recent hardship as an appeal to the sympathy of the court. Olbermann had been with the network since being fired from his longtime employer, MSNBC.

"He spent last fall talking to all the major networks, and he couldn't get a job. The idea was, this could be the last money he ever earned," a source told Politico.

He reportedly had dinner in New York recently with the head of the ESPN network, John Skipper.

"Clearly he was looking to see if there was an entry point to come back," Skipper said of the evening.

In 2010, he was let go from MSNBC a little over a month after serving a two-day suspension for declining to report political donations to his bosses that he made to leading House democrats' campaigns, including those of Arizona's Raul Grijalva and Gabrielle Giffords. The year prior, he lost his pregame role on NBC's "Football Night in America." Prior to that, he was a commentator on ESPN's SportsCenter alongside analyst Dan Patrick.

Some say that Keith Olbermann's lack of being able to find steady commentary work is because he has had issues with co-workers over the years. Current TV said one of the reasons for his dismissal was the fact he did not show up for work several times. They also said he no longer matched up with the network's values of "respect, openness and collegiality."

When asked what he thought of Keith Olbermann's possible return to "SportsCenter," Patrick quipped, "If he does return, I won't be back there with him, I can tell you that!" Keith Olbermann has been criticized numerous times for his harsh oft-personal criticism of his opponents. Communications Strategist Jason Maloni once compared his persona to that of histrionic football player Terrell Owens.

While at MSNBC, he had an ongoing "war" of sorts with timeslot rival Bill O'Reilly of FOX News. Though O'Reilly often expressed distaste for Olbermann's show and his commentary, he allegedly never mentioned the "Countdown" star by name, instead referring to the liberal talker as a "character assassin." Olbermann often referred to his rival as "Billo the Clown," and continuously harped on a workplace lawsuit brought against O'Reilly by a former staffer.

Keith Olbermann is also well known in media circles for a 10-minute defamatory address to his "Countdown" audience directed at then-President George W. Bush. In the monologue, Olbermann bitterly criticized the president for the issues he saw with his presidency, finishing the "special comment" by turning to the camera and saying curtly: "This advice, Mr. Bush ... Shut the hell up!"

Conservative Constitutional lawyer and talk show host Mark Levin has also traded barbs with Keith Olbermann over the years. Olbermann once accused Levin and fellow talker Laura Ingraham of "hat[ing] our troops." After the accusation by Olbermann, Levin told the Radio Equalizer that the converse was true.

"Keith Olbermann is Tokyo Rose in a rented suit [referring to the nickname for Japanese media propagandists during World War II] ... He's on my radar screen now as is anyone who smears America's military."

Radio analyst John Gibson told his audience in 2010 that Keith Olbermann allegedly would occasionally not show up for work at MSNBC during the Monica Lewinsky scandal, saying that the commentator "could not stomach" criticizing a fellow liberal, President Bill Clinton. Gibson said he was often called in to substitute for Olbermann in those circumstances, as Gibson also previously worked for the network.

Most recently, Olbermann tweeted a shot toward his former employer, MSNBC.

"So, four different 8 PM shows in 27 months. Good luck out there, Chris Hayes," referring to Hayes' upcoming replacement of Ed Schultz who currently holds Olbermann's 8 p.m., ET, slot. Olbermann was replaced by former New York Governor Eliot Spitzer at Current TV.