Sports and political analyst Keith Olbermann, best known as a long-serving host on MSNBC's weeknight political commentary program, Countdown with Keith Olbermann, has enjoyed dating relationships with some prominent names in the past.

However, Olbermann prefers to keep those relationships inside his hat. Not only that, the sports journalist has not converted his relationships with girlfriends into marriage.

Get along to learn more about his personal life, career, and net worth!

Olbermann's List of Girlfriends Includes Rebecca Lobo and Laura Ingraham

The Countdown with Keith Olbermann host was previously in an open relationship with a broadcast journalist Katy Tur. The former couple started dating in 2006 when Tur was in her mid-20s and Olbermann was 25 years her senior.

But their relationship ended three years later, in 2009.

Speaking to The New York Times in 2017, Tur talked about her relationship with Keith and what happened after their breakup.

"Keith is a wonderful human being," she stated. She further added, "He is my friend. He will always be my friend."

Presently, Tur is married to her husband Tony Dokoupil, co-anchor of CBS This Morning.

Moving on, the 62-year-old Olbermann had also dated American basketball analyst Rebecca Lobo in 1995 and Laura Ingraham in 1997.

His Abstruse Married Life Has Raised Questions on His Sexuality

After his relationship with Tur ended in 2009, Olbermann has not been involved in an affair, or at least he has not made it public.

Because of his multiple unsuccessful relationships and private personal life, people started questioning his sexuality by suspecting if he was gay.

Adding to the rumors, he gave his viewpoint about gay marriage in his program Countdown with Keith Olbermann in June 2011. He defended gay marriage, stating that gay marriage is a question of love.

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His opinion upon gay marriage swirled rumors about him being gay. However, his name entangled with women in the past inevitably falsifies the rumors. Yet, he has not commented on anything regarding the talks. 

As of this writing, Olbermann is reportedly unmarried and is waiting for a perfect partner to be called a wife.

Olbermann Was Raised by Parents in Westchester County

The veteran media person was born on January 27, 1959, as a son of a commercial architect father, Theodore C. Olbermann, and a preschool teacher mother, Marie Olbermann.

His family lived in Westchester County, where he was raised along with his younger sister, Jenna.

Olbermann lost his father on March 13, 2010, because of complications from colon surgery that was done in September 2009.

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Previously, in April 2009, nearly a year before his father passed, the political analyst had also lost his mother due to a brief battle with cancer.

Moving on, Olbermann, who stands at the height of 6 feet 3 inches (1.92 meters), completed his school education at Hackley School in Tarrytown. He received his graduate degree with a BS in communication from Cornell University's School of Agriculture and Life Sciences in 1979.

His Career on Sports Journalism

Olbermann launched his professional career from the UPI news agency and the RKO Radio Network. After that, he joined CNN in 1981.

He acted as a sports anchor in WCVB-TV in 1984 and worked for the virtual channel, KTLA-TV, and KCBS-TV.

His career took a significant turnaround when he was associated with the ESPN network in 1992, co-hosting SportsCenter in 1997. Later, he became a producer and anchor for Fox Sports Networks from 1998 to 2001.

He hosted Countdown with Keith Olbermann on MSNBC from 2003 to 2011 and on the Current TV network from 2011 to 2012.

He is also a writer who has written columns for various publications, such as The New York Times, Times, Sports Illustrated, and Playboy.

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Apart from journalism, Olbermann has also manifested his acting skills on an adult animated comedy-drama series, BoJack Horseman. He landed the role as a Tom Jumbo-Grumbo, a blue whale newscaster on the MSNBC network on several episodes of the series.

Olbermann's ESPN Saga: Return & Departure 

It was announced on July 17, 2013, that Olbermann would host a one-hour nightly show on ESPN, which would allow him to deviate from the topic of sports into realms such as politics, pop music.

But in 2015, Olbermann was suspended by ESPN for the week following Penn State University's annual philanthropy THON as he had stated, "PSU students are pitiful," which instantly pissed off Penn's supporters.

Later, he thanked the students and alums of Penn State for proving his point about the mediocrity of their education and ethics.

Olbermann formally apologized to them on his program after returning but noted batting practice ended for him.

However, in July 2015, ESPN announced that Olbermann would depart from the networks and implied it as a "business decision to move in another direction."

In January 2018, he made his third return to ESPN, presenting occasional commentaries on SportsCenter during 2018. However, his return was only for a couple of years, as he finally quit the network in October 2020.

As of August 2021, he no longer is associated with any sports networks - and he is actually busy running politics shows on his YouTube channel.

His Multiple Awards And Whooping Salary

For his remarkable work in the ESPN network, Olbermann won a Cable ACE award for Best Sportscaster in 1995.  He also received an Edward R. Murrow award for his coverage of the terrorist attacks on September 11, 2001.

Moreover, he is the recipient of 11 Golden Mike Awards for Best Sportscaster and was named the Sportscaster of the Year three times.

Olbermann has been associated in the field of sports journalism for more than 20 years. And with that, he has collected the paychecks from the various networks during his career.

As a result, as of 2021, he earns an astonishing annual salary of $2 million and owns a net worth of $25 million.