Keith Olbermann, a sports and political pundit best known as the long-serving anchor of MSNBC’s evening political commentary show Countdown with Keith Olbermann, has had previous relationships with several notable figures.

Olbermann, on the other hand, likes to keep his personal connections private. Not only that, but the sportswriter hasn’t tied the knot with any of his girlfriends.

Learn more about his personal life, work, and net worth by following along!

Rebecca Lobo and Laura Ingraham are among Olbermann’s girlfriends

The anchor of Countdown with Keith Olbermann was once engaged to television journalist Katy Tur. When Tur was in her mid-twenties and Olbermann was 25 years her senior, the former couple began dating in 2006.
But, three years later, in 2009, their relationship came to an end.

Tur discussed her relationship with Keith and what transpired following their divorce with The New York Times in 2017.

She described Keith as a “great human being.” She went on to say, “He is a close buddy of mine. He will always be one of my closest friends.”

Tur is now married to Tony Dokoupil, the co-anchor of CBS This Morning.

In 1995, the 62-year-old Olbermann dated American basketball expert Rebecca Lobo, and in 1997, he dated Laura Ingraham.

His enigmatic married life has sparked debate about his sexuality.

Olbermann hasn’t had an affair since his relationship with Tur ended in 2009 or at least hasn’t made it public.

People began to wonder about his sexuality, assuming he was homosexual, as a result of his numerous failed relationships and secluded personal life.

In June 2011, he offered his opinion on homosexual marriage on his show Countdown with Keith Olbermann, fueling the suspicions. He justified homosexual marriage by claiming that it is a matter of love.

His stance on homosexual marriage sparked speculations that he was gay. His prior associations with women, on the other hand, surely disproves the allegations. Despite this, he has remained silent in the conversations.

As of this writing, Olbermann is said to be single and looking for the right companion to call his bride.

Keith Olbermann was raised in Westchester County by his parents

Theodore C. Olbermann, a business architect, and Marie Olbermann, a preschool teacher, gave birth to the seasoned media personality on January 27, 1959.

His family resided in Westchester County, where he and his younger sister, Jenna, were reared.

On March 13, 2010, Olbermann’s father died as a result of complications from colon surgery performed in September 2009.

Prior to his father’s death, the political analyst had lost his mother to cancer in April 2009, over a year before his father died.

Moving on, Olbermann, who measures 6 feet 3 inches (1.92 meters) tall, completed his schooling at Tarrytown’s Hackley School. In 1979, he graduated from Cornell University’s School of Agriculture and Life Sciences with a bachelor’s degree in communication.

His Sports Journalism Career

Olbermann began his professional career with the RKO Radio Network and the UPI news agency. After that, in 1981, he joined CNN.
In 1984, he served as a sports anchor for WCVB-TV, as well as the virtual channel, KTLA-TV, and KCBS-TV.

When he joined the ESPN network in 1992 and co-hosted SportsCenter in 1997, his career took a dramatic shift. From 1998 to 2001, he worked for Fox Sports Networks as a producer and anchor.

From 2003 to 2011, he anchored Countdown with Keith Olbermann on MSNBC, and from 2011 to 2012, he hosted Current TV.
He is also a columnist for a number of magazines, including The New York Times, The Times, Sports Illustrated, and Playboy.

Apart from journalism, Olbermann has also acted in an adult animated comedy-drama series called BoJack Horseman. On numerous episodes of the show, he played Tom Jumbo-Grumbo, a blue whale newscaster on the MSNBC network.

The Return and Departure of ESPN’s Keith Olbermann

On July 17, 2013, it was revealed that Olbermann will headline a one-hour weekly program on ESPN, allowing him to go away from sports and into areas such as politics and pop music.

However, during Penn State University’s annual fundraiser THON in 2015, Olbermann was banned by ESPN for a week after saying, “PSU students are sad,” which infuriated Penn State fans.

Later, he commended Penn State students and alumni for demonstrating the mediocrity of their education and ethics.

After returning to his show, Olbermann publicly apologized to them but observed that batting practice was over for him.

However, ESPN announced Olbermann’s departure from the networks in July 2015, citing a “business choice to proceed in another path” as the reason.

He returned to ESPN for the third time in January 2018, providing infrequent commentary on SportsCenter. His comeback, however, was limited for a few years, since he left the network in October 2020.

He is no longer affiliated with any sports networks as of August 2021, and he is instead busy doing political programs on his YouTube channel.

His awe-inspiring salary and a slew of awards

Olbermann got a Cable ACE award for Best Sportscaster in 1995 for his outstanding performance on the ESPN network. He also won an Edward R. Murrow award for his coverage of the September 11th terrorist events.

In addition, he has won 11 Golden Mike Awards for Best Sportscaster and three times been voted Sportscaster of the Year.

For more than 20 years, Olbermann has been linked with sports journalism. And with that, he’s been able to earn salaries from multiple networks throughout his career.

As a consequence, as of 2021, he makes a whopping $2 million each year and has a net worth of $25 million.