"He's a man of the people," Ruck said. "He connects with people."
Greenlee used his connections and his deep pockets to establish himself as arguably one of the top five executives in history of "black baseball." He owned and ran the Pittsburgh Crawfords, a franchise that dominated the Negro Leagues in the 1930s.
Originally from Marion, N.C., he moved to Pittsburgh in 1920 and started building a fortune in illegal gambling, a shadowy enterprise that prospered in black neighborhoods during the Great Depression.
While some people frowned on gambling, Phil Dixon, a respected authority on the Negro Leagues, said Greenlee's involvement in the numbers game shouldn't be viewed any differently than the lottery operations that state governments run today.
"Banks wouldn't give loans to black people," Dixon said. "People from Kansas City could point to some institutions that were built by the money of Gus Greenlee."
Using his numbers money, Greenlee bought the Crawfords in 1930. But he wasn't satisfied with just owning a professional team. He wanted to win.
In that regard, he didn't differ from many owners today. Greenlee went out and bought some of the Negro Leagues' best players. Hall of Famers like Satchel Paige, Josh Gibson, Oscar Charleston, Judy Johnson and Cool Papa Bell all played for Greenlee's Crawfords at some point during their careers.
"He paid top dollar at the time," Ruck said. "Gus fought big."
Greenlee used his fighting power to recruit many of the aforementioned players away from another Negro League powerhouse of the era -- the storied Homestead Grays, a team his Pittsburgh rival Cum Posey owned.
"What he did, for the most part, was find opportunities for black athletes," Dixon said. "He made Pittsburgh a center of good baseball."
In 1935, Greenlee's ballclub officially became the center of black baseball, supplanting the Grays. For it was during that '35 season that the Crawfords won the Negro League championship.
"He stole the nucleus of the '31 Grays, and that's his team." Dixon said of the '35 Crawfords. "It was an awfully strong team."
Unlike most Negro League owners, Greenlee built his Crawfords their own ballpark in 1932. He named the place "Greenlee Field," which was the first black-owned, black-built ballpark in the country. It gave his franchise the kind of financial independence that few Negro League teams had.
Before then, Negro League teams were at the mercy of white promoters. They were the ones who booked the best venues.
With his own ballpark, Greenlee controlled whhich teams played in his stadium and when. Black college football teams used Greenlee Field for practices; so did the Pittsburgh Pirates, an NFL team that eventually became the Steelers.
"It's a very concrete and real manifestation of a larger effort in the black community to control its own sporting life and economic institutions." Ruck said.
As a baseball innovator, Greenlee didn't stop at just owning the field, though. He also helped create the East-West All-Star Game, the signature sports and cultural event for blacks at the time.
"It wasn't just baseball," Ruck said. "It was black America in the North coming together in Chicago for those games."
The All-Star Game drew large numbers of black fans. Held each year at Comiskey Park in Chicago, the event outdrew the Major League All-Star Game from 1933 to 1950.
"In 1938, the largest crowd they drew for any of their games was 6,000 people," Dixon said. "When those same players go to the East-West game, they go before 24,000. It didn't compare to other games."
Greenlee's successes as an owner didn't last much beyond the '38 season. Greenlee, one of many Negro League owners who made their money in gambling, sold the Crawfords to a group of white businessmen in 1939. His ballpark was destroyed soon after.
"The more the numbers came under scrutiny, the more pressure they put on these guys," Dixon said. "They were making a lot of money."
Greenlee died July 10, 1952, of a stroke. But he wasn't forgotten in the black community or in baseball history.
People familiar with The Hill and baseball fans alike remember him as a man who was ahead of his time, Dixon said.
"For a long period they made this country go," Dixon said of owners like Greenlee. "They changed the whole economy of the black community."