Veeck's incisive stories on the 1910-era Cubs and his private conversations with new Cubs owner William Wrigley Jr. led to Veeck Sr. being hired as the team's president in 1919.
Shortly after that, he began a spirited campaign to get rid of gambling, which was prevalent in baseball at the time. Dickson said Veeck Sr. believed and implied in his newspaper reports that certain members of the Cubs may have accepted bribes to throw the 1918 World Series, which they lost to the Boston Red Sox.
"Veeck knew about gamblers being present in the park, and there was only so much he could do about that," Dickson said. "But he wanted to make sure that with regards to bribing players, it was a river that no one should cross."
By the mid-1920s, Veeck Sr. was established as one of baseball's leading executives.
Even before then, William Veeck aimed to make Wrigley Field more of a family-oriented setting. He instituted the first Ladies Day there in 1919, where women got in free on select game days, a promotion that lived on at Wrigley into the 1970s.
Veeck Sr. also worked with William Wrigley to modernize Wrigley Field, double-decking the stadium in the mid-1920s, which helped give the structure the look that it has today.
He and William Wrigley pioneered broadcasting Cubs games regularly on the radio, beginning in 1923 on WMAQ.
"All the other teams were adamant against broadcasting games, believing that it would take away from their gate," said Tim Wiles, director of research for baseball's Hall of Fame. "But Veeck thought it would be great advertising for the Cubs. It turned out not only to be great advertising, but also another great revenue stream for the owners."
As a result of these marketing and broadcast innovations, attendance increased by 117 percent for the Cubs at Wrigley during the 1920s, while other teams saw only a 27 percent attendance spike during that time, according to the late historian and journalist Warren Brown, who wrote a book in the mid-1940s about the Cubs' early years.
"Veeck's motto was: We want you to be safe, comfortable and happy in the ballpark, and that wasn't the way many owners thought of it," Wiles said. "Most owners wanted to get people through the gates and weren't concerned with the overall experience."
Veeck Sr.'s final great accomplishment was building the pennant-winning Cubs teams of the late 1920s and early 1930s. Behind stars acquired by Veeck Sr. — Hack Wilson, Charlie Grimm, Rogers Hornsby and others — the Cubs won the National League pennant in 1929, 1932 and 1935. Even the 1938 Cubs pennant-winning squad had some players acquired by Veeck Sr., including Grimm.
"Just the fact that he was able to get any Cubs team to win a pennant is impressive to me," said his great-grandson Night Train Veeck, 26, an account executive in sales for the White Sox.
Night Train is the fourth generation of Veecks to work in a Chicago major league front office. His father, Mike, worked under Bill with the White Sox in the 1970s. (Night Train got his name in tribute to Dick "Night Train" Lane, a defensive back for football's Chicago Cardinals in the 1950s.)
Night Train said he will support any efforts to get his great-grandfather in the Hall of Fame.
"Of course, I'm biased," Night Train said. "But he seems very deserving of the honor."