"Bolden was one of those early entrepreneurs in the game of baseball that was a pioneer before his time," Philadelphia Tribune sportswriter Chris Murray said.
A major player in black baseball's heyday, Bolden was an owner who had an undying devotion to bringing order and organization to the sport he loved. An unassuming rules-maker from eastern Pennsylvania, he proved to be the antithesis of Hall of Famer Rube Foster, an iconic figure in the game.
Foster, who formed the Negro National League in 1920, was the first black executive to coordinate league play. But just three years after Foster established the NNL, Bolden envisioned another, even more successful league. His league would butt heads with Foster's.
"The best clues that you get about Bolden and Foster's relationship, sadly, comes from the comments they would make about one another in the black newspapers at the time," said Leslie Heaphy, an authority on the Negro Leagues and an associate history professor at Kent State University-Stark. "By that point, they were not necessarily always friendly to one another, because Bolden was certainly seen by Foster as a great deal of competition."
In 1923, as Foster's league experienced financial difficulty, Bolden formed the Eastern Colored League. He was hoping that another organization would not only take black baseball to more populated regions of the United States -- Foster's league operated primarily in the Midwest -- but it would also expose its players to Major League teams and scouts, further promoting the case for integration.
"They came to respect the decisions they both made," Heaphy said of Foster and Bolden. "In the long run, the establishment of the Eastern Colored League was certainly a significant boost to Foster's goal."
The creation of both leagues led to the first Negro League World Series in 1925, and Bolden's Daisies beat the Negro National League champion Kansas City Monarchs. During a stretch from 1923-1927, the Daisies won three Eastern Colored League pennants and solidified Bolden's place as one of black baseball's most successful owners.
Working in Philadelphia alongside booking agent Nat Strong and wealthy white sports financier Eddie Gottlieb, Bolden implemented his designs of teamwork and task-delegation.
"Unlike Foster's league, where he was the president and had other commissioners underneath him, the group that worked with Bolden when the Eastern Colored League was organized worked together," Heaphy said. "They actually worked as a committee."
Still, Bolden was seen as the Colored League's primary leader, although teams didn't exactly elect him league president as team owners did with Foster, who ruled the Negro National League with an iron hand. Foster placed himself in charge of overseeing all aspects of his league, including booking and publicity.
The teams in Bolden's league did much of that publicity themselves, and Strong served as their booking agent.
"It's cliche to say because of his name, but the league was very strong under Strong," Heaphy said. "He had a lot of connections and was well established by the time the Eastern Colored League came along."
Few would argue that, even with Strong's role in booking games, Bolden wasn't the sole guiding force behind the league.
Unlike most black baseball executives, Bolden lived his entire life in the communities his teams called home. A postal clerk who belonged to several fraternal and social organizations in Philadelphia, he built an extensive network there, even befriending reporters at the black-owned, black-operated Philadelphia Tribune.
In 1916, when Bolden took over the semipro Hilldale franchise, his relationship with the newspaper blossomed after he asked The Tribune to cover his team's games. It was an uncommon practice during the era, but Bolden saw it was a way for his teams to receive free advertising and publicity.
"This shows he was a smart man," Murray said. "At that time, the black press was at its zenith. It played a tremendous hand in not only highlighting the best players in the Negro Leagues, but it played a big advocacy role in getting blacks integrated in the game of baseball.
"While it's not clear who he knew at the paper, the fact that he found a way to use it as a marketing tool was very smart."
By his death in 1950, Bolden saw baseball integrated, which signaled rapid doom for black leagues. His death transferred ownership of his second team, the Philadelphia Stars, to his daughter -- 46-year-old pediatrician Hilda Bolden Shorter. Headlining a short list of female black team owners, Dr. Shorter was the rare example of a daughter who took command of her father's franchise.
Typically, women who began owning teams did so after their husbands died, Heaphy said.
Respect for her and her father never seemed to be an issue.
"If he couldn't run the business, and the team wasn't successful and they weren't getting paid, then he clearly didn't belong there at all," Heaphy said of Bolden. "But that's not how he was.
"He brought something to the team. He was a success."