That's a question that has long weighed on Bob Kendrick, marketing director of the Negro Leagues Baseball Museum.
And Kendrick's answer? It comes in the form of a reflective shrug.
"We get somewhat infatuated with the lore and legend surrounding some of these almost mythical figures like Satchel Paige," Kendrick said. "But when we start to think about the executives, they've never been a point of emphasis."
Even though historians have mined the archives, the newspaper clippings and the oral histories, and sports journalists have written countless stories for Black History Month about black baseball, those strong-willed owners and astute executives have seldom gotten their due.
Ask people about Hall of Famers Paige, Oscar Charleston, Buck Leonard, Josh Gibson, Willie Wells or Leon Day, and people might say, "Yeah, I know of 'em."
But ask about Rube Foster, Effa Manley, Cum Posey, Alex Pompez and J.L. Wilkinson -- all of them enshrined in Cooperstown -- and few can point to their contributions to black baseball.
From Foster to Manley to Posey, from Gus Greenlee to Tom Wilson to the brothers J.B. and B.B. Martin, and from Ed Bolden to C.I. Taylor to James Semler, they were all pioneers.
Forgotten pioneers -- now more than then.
"Their story would not get told because they were marked men," said Adrian Burgos Jr., a history professor at the University of Illinois and an authority on black baseball. "They were individuals who had run a racket that existed in the shadow of 'Organized Baseball,' which was deemed inherently better."
Inside that thinking was the belief that if the game were better, then the ownership was better, brighter and more visionary.
The sometimes shadowy figures who often did own teams in the Negro Leagues and in their predecessors were never considered a match for the titans of American industry, the men that held stakes in Major League teams.
Historians like Burgos dispute such thinking. They marvel at the successes of these all-black teams even as they operated along the margins.
The reason for that success isn't a secret: enlightened leadership.
No enterprise can thrive absent that sort of leadership, said Christian Resick, assistant professor of management at Drexel University.
Resick, who has studied leadership in baseball, saw a combination of factors that played a role in ensuring the viability of those franchises and black leagues. He pointed to work ethic, willingness to sacrifice for the greater good and strong organizational and communication skills as central characteristics of enlightened leadership.
"That ability to really see where the club and the organization can go seems to be another of those characteristics," Resick said. "Great leaders are visionaries and are committed to that vision."
Visionaries are often dreamers, and it took men and women with grand dreams to mold a loose federation of barnstorming teams into a league. It took strong will and determination to hold that league together and make it thrive.
"But black baseball owners had their own squabbles just like Major League owners did," Burgos said. "They couldn't agree on a commissioner, and they had a hard time determining what was best for the interest of the entire league.
"A lot of times they voted for leadership not on what was really in the best interest of the institution, but on what was best for themselves."
Against all these internal struggles and pettiness, black leagues thrived. They produced a high-energy, showy brand of baseball that rivaled anything seen in the Major Leagues.
No telling what the Negro Leagues might have become if segregation had persisted. What allowed the leagues to thrive ended up killing them when segregation gave way to integration.
The Negro Leagues then disappeared into history, and the men and women who made black baseball successful faded into history as well. Historians and fans, however, should not ignore the contributions of these owners and league executives to the sport.
With more than a handful of them honored for their contributions with a plaque in the Hall of Fame, the question is who were the most influential owners and executives. Were owners like Manley, Foster and Posey more influential than the Martin brothers, Taylor or Greenlee?
Who are the five owners/executives who made black baseball what it became before it vanished into the pages of history books?