Just saw this tweet about somewhat long in the tooth English footballer James Milner:
This guy points out James Milner(born 1986) played under the same legendary england manager (Bobby Robson) as post war footballer Johny Haynes(born 1934), though not at the same time (Haynes played under Robson twenty years before Milner was born)
What is the most extreme example of this? I’m assuming this case is not an outlier.
Connie Mack managed for 53 years, so I’m guessing he would have the widest gap. Jack Glasscock, born 1857, played shortstop for the 1894 Pittsburgh Pirates. Carl Scheib, born 1927, pitched for the 1950 Philadelphia Athletics. That’s a 70 year gap…
If we consider just English football managers, Roy Hodgson may well have this beaten, given he began managing in 1976 with Halmstad in Sweden and only retired earlier this year after a short spell at Watford. That is a career spanning 46 years, so if one of his Halmstad players was at least 6 years older in '76 than one of his Watford players in '22, which surely must be the case, then that is 52 years too.
This one is a bit of a cheat:
Tony La Russa ‘managed’ Minnie Minoso (b. 1923) in 1980 and Lenyn Sosa (b. 2000) in 2022.
That seems reasonable I’m going to say the biggest gap is:
Hans Selander, Halmstad, Right Back, born 1945.
Vicent Angeleni, Watford, Goalkeeper, born 2003.
58 years
In AFL Jock McHale, who spent his entire career (1902-1949) playing and coaching with Collingwood commenced coaching in 1912.
By my estimation the oldest player on his 1912 squad was Ted Rowell born 1876.
By my estimation the youngest player on his 1949 squad was Bill Rose born in 1931
That’s 55 years.
George Halas, founder and owner of the NFL’s Chicago Bears, coached them, on and off (mostly on) from their founding as the Decatur Staleys in 1920, until he finally retired from coaching 1967.
Pro Football Reference doesn’t have a compete roster of the 1920 team, but the oldest player I can find in the limited info on that page is Hugh Blacklock, born in 1893. It appears that the youngest players on the '67 Bears (their new draft choices) were born in 1945, so that’s a spread of at least 52 years (I say “at least,” as it’s possible that they had someone older than the 27-year-old Blacklock in 1920).
He doesn’t beat some of the others in other sports, but Halas had the longest tenure of any NFL coach.