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Like his paranoia, Whitlock's love of sports started early. He was a standout offensive lineman at Warren Central High School in Indianapolis, blocking for future NFL player Jeff George, the man with the million-dollar arm and the plug-nickel disposition. Whitlock earned a football scholarship to Ball State, but he ended up on the bench and realized that his pro-ball prospects were fading fast.
David Knott was the faculty adviser for The Ball State Daily News when Whitlock started exploring sportswriting during his junior year.
"When he first got there, his writing skills had some pretty rough edges," Knott says. "But he was a hard worker, and he was determined to become a good writer."
Knott recalls that Whitlock mostly filed game reports and wasn't much of a presence in the newsroom. "He was the football player who came to work for the paper, you know what I mean?" he says. "He didn't hang out. He was busy with football, too."
Whitlock wasn't impressed with the region's sports columnists, Knott says.
"He thought they weren't being hard enough on the teams, and he was exactly right," Knott says. "On the other hand, that wasn't the style in those days, especially not in Indiana."
Whitlock also disliked the local columnists' impersonal third-person voice.
"One of the things I always preached as a journalism professor, especially in column writing, was that the columnist should keep the I out of it," Knott says. "Jason definitely did not agree with me on that, and who am I to argue with the success he's had?"
Whitlock eventually earned an apprenticeship at The Herald-Times in Bloomington, Indiana. There, he worked for sports editor and Bob Knight biographer Bob Hammel, who still remembers marking up Whitlock's first story.
"It looked like a red-ink pen had bled to death," Hammel says. "I told him, 'I don't know how serious you are with this. You are going to have to learn a lot of things really fast.'"
Hammel suggested to Whitlock that he read James Kilpatrick's syndicated Sunday newspaper column, The Writer's Art. When Hammel left at 2 a.m., he saw only one light in the newsroom still on. It was at Whitlock's desk. In front of Whitlock were back issues of the paper's Sunday edition, opened to Kilpatrick's column. The scene convinced Hammel that maybe Whitlock had a chance.
During Whitlock's year at the Herald-Times, he and Hammel made an odd pair. Hammel says that Whitlock charmed his wife and took obvious pleasure in arguing the conservative counterpoint to Hammel's liberal politics.
"I think he sort of emulated a rising genre of cynical writing," Hammel says. "That's the vogue right now, and he rode that wave and represents it to many people."
After brief stints at the Charlotte Observer in North Carolina and The Ann Arbor News in Michigan, where he called for the benching of then-University of Michigan quarterback Elvis Grbac in his first column, Whitlock moved to the Star in October 1994. He soon found that the daily's history of sports reporting was dominated by the 44-year reign of Joe McGuff, who deserves some credit for bringing the Royals to town.
"He's not as big as Joe McGuff," says Tom Shattel, a Kansas City native who worked for the Star before moving to his current position as a sports columnist for the Omaha World-Herald. "Nobody will ever be that big. In this era of loud and brash and in your face, [Whitlock is] a different kind of Joe McGuff. He's a different kind of celebrity."
McGuff, who joined the Star in 1948 and retired in 1992, was the calm, reasonable voice of the Star's sports page. A member of the Baseball Hall of Fame's writers' wing, he was popular with athletes and colleagues. George Brett renamed his ALS charity golf event after McGuff last year.
The Star has showcased other caustic columnists, notably Dick Mackey. And there was Jonathan Rand, who was critical yet by-the-book. But no one aggressively crossed lines like Whitlock does. No one even came close to his nasty personal vendettas.
Not coincidentally, Whitlock has tapped into markets that have usually been difficult for the Star to reach, attracting young readers and African-American fans. His column was a Public Enemy track in the paper's Barry Manilow mix tape.
Teaming Whitlock with optimist Joe Posnanski gives the Star a "perfect mix" of columnists, says Rick Dean, sportswriter for The Topeka Capital-Journal. "They've got the rabble-rouser, and they've got the poet," he says.
But Whitlock's arrival here was not without its bumps. Sportswriters travel in herds. They attend the same press conferences. They ride the same elevators to the same press boxes at stadiums. Occasionally, they carpool to games and events. Kansas City has historically been even more insular.
"Kansas City media for years had been almost a fraternity," Shattel says. "Here comes Jason, who was from Michigan and had a certain style and was not one of the boys."
Shattel remembers Whitlock sitting by himself in the Arrowhead Stadium press box during Chiefs games that first season. "I thought, that's not right," Shattel says. "I felt bad for the guy at first."