Those Guys Have All the Fun - James Andrew Miller [115]
It is said that Olbermann decided what his career would be when he was eight years old: he’d be the game announcer for the New York Yankees. And with that decision out of the way, he continued and eventually completed his childhood—most of it lived within the beautiful confines of Hastings-on-Hudson in Westchester County, an affluent bedroom community north of New York City. Lore has it that a company that manufactures baseball trading cards “published” Olbermann’s first book, The Major League Coaches, 1921–1973 (well, a friend made one hundred copies of the manuscript) when he was fourteen. Olbermann has a talent that can’t be taught. He can relate to people on the other side of the camera and, indeed, relate to the camera itself, in a way that comes across as second nature. And yet he once told an interviewer that on some level, he’s always making fun of television: “Like, ‘look how ridiculous this is, me sitting here and you sitting on the other end, watching me—what are you doing that for?’ I think that’s always been my attitude.”
Olbermann’s father was an architect; his mother was a teacher and lifelong Yankees fan. Even as a child, Olbermann was a baseball fanatic, listening to games on the radio in his room at night when his parents curtailed his TV viewing and shut off his bedroom light.
If you’re going to write a book at fourteen, you might as well enter an Ivy League university two years later, which is what Olbermann did. He enrolled at Cornell and, being no slouch at academics, graduated in 1979 at the age of twenty. While at Cornell, he anchored a daily sportscast on a commercial ABC-affiliate radio station run by some of his fellow students. Olbermann wore a number of hats at the station, including sports director, newscaster, vice president of training, and operations manager.
Olbermann first found regular employment as a sportscaster at UPI Radio Network (1979–1980) and later at RKO Radio in New York (1980–1982), where his boss was none other than Charley Steiner. Even in small-time jobs, Olbermann gave off sparks that made him an unusually compelling figure on the air—but he also polished his image as a backstage bad boy who rebelled against management and saw almost any criticism as persecution.
In 1981, Olbermann got his big break when CNN hired him as a sports reporter in New York, replacing a woman by the name of Debi Segura who moved to Atlanta to be with her husband, Lou Dobbs. While at the pioneering news network, Olbermann was subsequently promoted to anchor and earned a considerable amount of attention, but he quit after only three years, spending the rest of the decade bouncing among local stations in Boston and Los Angeles.
ESPN had first approached Olbermann way back in 1982, but shortly after his arrival in 1988, Walsh began his own pursuit. He offered Olbermann the 11:00 p.m. SportsCenter, cohosting with Chris Berman. Olbermann declined. After the Major League Baseball deal was completed the following year, Walsh and Steve Anderson asked Olbermann if he would fly from Los Angeles to Bristol every weekend to host the new Baseball Tonight, but again, the answer was no. Finally, by August of 1991, Olbermann agreed to come to ESPN the following spring as an anchor for the 11:00 p.m. SportsCenter. In the last year of his contract with KCBS—which they chose not to renew—he had been making $475,000. His starting salary in Bristol would be just over $150,000.
KEITH OLBERMANN:
There were no jobs open in any of the big markets. I wanted to be back East to be closer to my family. I had no doubt of my skills and