Published totals from local newspaper accounts covering his 30-plus year career provide a glimpse at his prowess on the diamond.

He played for the Missouri Black Tigers of nearby Higbee, in 1908, and subsequently for the Hannaca Blues, an all-black contingent from Glasgow during the 1909–1910 seasons.

Together, the group of about 20 players crisscrossed the upper Midwest, playing ball during the day and providing an evening minstrel program for their mostly white ticket buyers.

He contracted to pitch for the World's All Nations team based in Des Moines, Iowa, in 1912,[4] for a reported sum of $150 per month.

Most of his accomplishments were against semi-professional competition, but Donaldson also did very well in his relatively few contests against highest level professional baseball teams, and there were a number of first-person reports of his talent from such opposing managers and players.

[citation needed] Donaldson and his ball-clubs prior to the organization of the Negro National League in 1920 played ball all year round, both in the Midwest and venues as far west as Los Angeles[6] as far east as Palm Beach, Florida.

[2] After World War I, J. L. Wilkinson formed the Kansas City Monarchs in 1920, where the 29-year-old Donaldson worked as a pitcher and center fielder.

However, for at least two years, Donaldson managed and played on the revamped All Nations baseball team,[13] which now served as a way to train, recruit and make money for Wilkinson's "parent club", the Kansas City Monarchs.

Perhaps most impressive, Donaldson played in towns in Minnesota,[14] the Dakotas,[17] and Canada,[16] sometimes as the only black player on a small-town semipro team.

Like many black barnstormers of the time, Donaldson faced white Major Leaguers and fared well enough to prompt New York Giants manager John McGraw to say, "I think he is the greatest I have ever seen."

"[20] Newspapers and ball players often lied about their age throughout their career, for birth, marriage, and other government records show Donaldson was about 48 years old at the time.

[38] He pursued Willie Mays and Ernie Banks for the team and is credited with the signing of several prominent Negro leaguers of the time, including Bob Boyd and Sam Hairston.

At age 60, Donaldson was voted a first-team member of the 1952 Pittsburgh Courier player-voted poll of the Negro leagues best players ever.

[31] Donaldson died of bronchial pneumonia at age 79, in Chicago, and is buried in Burr Oak Cemetery in Alsip, Illinois.

In 2004, Jeremy Krock, of Peoria, Illinois, raised enough money for a proper headstone[39] via the Negro Leagues Baseball Grave Marker Project.

[37] Donaldson was nominated for a special ballot of pre-Negro leagues candidates for inclusion in the National Baseball Hall of Fame in 2005.

However in February 2006, Donaldson failed to garner the necessary 75% to earn election from a 12-member voting committee, appointed by the Board of Directors and chaired by former Major League Baseball Commissioner Fay Vincent.

On November 5, 2021, he was selected to the final ballot for the Baseball Hall of Fame's Early Days Committee for consideration in the class of 2022.