I think like most things in those times, it has been greatly exaggerated, and Greb may have beaten Dempsey or given him a tough fight but, the newspaper back then were keen on hyperbole's so it got blown out of proportion.
Amir Khan reportedly beat Manny Pacquiao up in sparring.
Hey, just saying.
And there's that well known footage of Mayweather getting worked over by Paul Spadafora.
Dempsey and Greb did spar and it's not out of the question that a small, quick and elusive fighter could make a heavyweight look bad for a few rounds. Jack Johnson reportedly had the same problem when he sparred the lightweight Jack Blackburn.
Most reports from newspapers (from that time) & articles suggest that Greb did indeed get the better of Dempsey in there sparring sessions. In one report I also heard Greb split Dempsey's lip open.
Greb always talked about how Dempsey couldn't beat him
The Dempsey camp wanted Greb as a sparring partner for
the first Tunney fight .but Greb refused because he felt Dempsey had no way to beat Tunney and would be stealing Dempseys money....Also Gibbons said the
reason Jack couldn't knock Himself and Greb or Tunney out was because he couldn't hit them...But having a great middleweight like Greb make Dempsey look foolish for a few rounds is different then making Dempsey say "No Mas"
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