In late 1895, he was implicated in a series of articles by Caspar Whitney alleging that the schools of the Western Conference had been corrupted by "professionalism" involving the payment of money to athletes for their services in playing football.

[1][2] He played two years of football for Hyde Park in the Cook County High School League.

[3] In November 1891, the Chicago Daily Tribune wrote: "Sherman at quarter back, although not a swift passer, is cool-headed and is nearly always to be found near the ball.

In April 1892, Sherman performed with Michigan's banjo and glee clubs at Chicago's Central Music Hall.

[11] In the fall of 1895, Caspar Whitney wrote a series of articles in Harper's Weekly contending that "professionalism" had corrupted collegiate athletics among the Western Conference schools, including Wisconsin, Northwestern, Minnesota and Michigan.

Whitney stood his ground and explained: As to Stevenson, I have charged he was offered $600 by Roger Sherman, as manager of the Michigan team, to play with that eleven.

"[15] In an essay published by The Inlander, Sherman wrote: In order to get the support of the college body and the public in general a team must first win at almost any cost.

... To declare for purity at the outset means a weak team and, as a consequence, defeat and lack of support, moral and financial, for years to come, maybe for ever.

The power that a manager has to help men through college, if judiciously exercised, is productive of a great deal of good.

[1][8] He began the practice of law in Chicago with his father, Penoyer L. Sherman, a master in the chancery court.

[1] Sherman was active in politics in Chicago's Sixth Ward and was appointed master in chancery of the Superior Court in 1906.