Roy played with the Chicago White Sox from 1923 until 1925, but he was considered a top prospect as far back as 1916, when he was recommended to the New York Giants by Zeke Wrigley, who played in the National League from 1896 to 1899. The Pittsburgh Pirates tried to purchase Elsh from the Sioux City Western League team in 1922, but was blocked by the White Sox, claiming that they had first crack at Sioux City players. The relatively new baseball commissioner, Kenesaw Mountain Landis, agreed with Chicago and the next season, Roy found himself starting in left field in the second game of the 1923 season, at Dunn Field in Cleveland. Elsh would steal a base and score a run in his MLB debut. He would steal twenty-four bases in his short career, while only being caught nine times.
As a thirty-two year old rookie, Roy didn't have much of an upside for the majors. His best season at the plate was in 1924, when he hit .306 and had an OPS of .731. As his career wound down, Elsh played each outfield position, pinch hit and even played a little first base, but he wouldn't stick around past a disappointing 1925, where he hit .188 with only one extra base hit, which was a double. He was runner up for the Western League batting title before his MLB debut, but after his MLB days ended in 1925, he slipped down to the A ball Dallas Steers in 1927, which was his last season.
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