[2] Barry was a well-established cricketer; and, according to the sporting journalist, former Fitzroy footballer, former Essendon football coach, and former Australian Test cricketer, Jack Worrall, writing in 1936, a significant historical error needed to be corrected: A decade earlier, Worrall had drawn these same facts to his readers' attention when criticizing the claim made by Bosanquet, in his article, "The Googly", in the 1925 edition of Wisden, that he (Bosanquet) had bowled the first-ever googly in Australia to Victor Trumper, in a match against New South Wales, in 1903: Although his first name was Edward, Barry was known during his career by the nickname "Son".

He joined Essendon, from Albert Park,[7] in 1896, after apparently trying out with South Melbourne in the pre-season, along with his Albert Park team-mate Mick Pleass,[8] before he was offered "all sorts of inducements" to move to Essendon.

[9] He played his first game for Essendon, against Melbourne, at the MCG on 2 May 1896, the first of the season's home-and-away matches.

[10][11] Playing as a "follower", Barry was one of the 20 who played for Essendon in its first VFL match against Geelong, at Corio Oval, on 8 May 1897: Jim Anderson, Son Barry, Arthur Cleghorn, Tod Collins, Jim Darcy, Charlie Forbes, Johnny Graham, Joe Groves, George Hastings, Ted Kinnear, George Martin, Bob McCormick, Pat O'Loughlin, Gus Officer, Ned Officer, Bert Salkeld, George Stuckey, George Vautin, Norman Waugh, and Harry Wright.

[12] He was a rover in the Essendon team that won the 1897 VFL premiership (there was no "Grand Final" in 1897).