[7] He next joined the Jackson, Michigan club of the Tri-State League but was released in early June along with Ed Flynn.
[8] In July, Sterling was playing for a minor league team in Ashland, Pennsylvania when he was signed by the St. Louis Browns.
[11][12] The following year, Sterling returned to Pennsylvania to play for Charlie Mason's minor league Philadelphia Giants.
[14] Sterling may also have been the pitcher for a team of locals picked to play an exhibition against the Athletics prior to the start of the 1890 season.
[19] York was replaced by William Primrose in early July and The Sun reported that the majority of the team's players were expected to be released.
[20] A day later, the Albany Morning Express reported that Sterling had been released, ostensibly due to drunkenness.
In September, William Whitaker announced the club was bankrupt and ownership was transferred to Billy Barnie, who also owned and managed the Baltimore Orioles.
The Athletics, as a result, filled out their roster with players who had limited playing experience and who agreed to receive a portion of ticket sales instead of a salary.
He pitched the entirety of a rain-shortened,[23] five-inning game against the Syracuse Stars on October 12, 1890 in front of only twenty spectators[24] in Gloucester City, New Jersey.
Sterling, who pitched "in a black cloth suit, with low cut vest and white stand-up collar" allowed 12 runs in his five innings of work.
[4] In August 1908, Sterling filed a personal injury suit seeking $5,000 in damages (equivalent to $170,000 in 2023) after being seriously injured in a fall on a sidewalk in Gloucester City.
Lacking any evidence to confirm these identifications, however, the Society for American Baseball Research (SABR) determined in 2007 that their biographical information would be removed and that their given names would be reclassified as unidentified.
[46] The only clue as to Sterling's identity came from the Philadelphia Inquirer's coverage of the game which identified him as a "young man of Camden.