Dempsey vs James Toney

Holyfield was the master of kicking his heels out (jumping in and out) he did beat Tyson who'd square up like Dempsey. Toney's shoulder roll might throw Jack off balance and reaching in plus Toney had a chin. Toney did go to the body a lot Jack's square stance might make easy for Toney to go to body.
One the other side of the coin Toney lost to RJJ who fought off the front foot like Dempsey it's doubtful that RJJ possessed the power of Dempsey.

 

Dempsey would have pounded on a heavyweight Toney, shoulder roll and all. Dempsey is going to be hitting Toney everywhere, legal and not legal.

 

Dempsey by late round KO or he pounds out an UD.

 

Dempsey doesn't turn up, colour line.

 

Dempsey would have out punched him .. Toney did not hit hard enough .. Jack would have been too busy and sharp hitting.

 

Toney of the Holyfield fight would have toyed with Dempsey. Dempsey with his crude swarming attack would have been a sucker for counter rights. Toney UD but very good possibility of a KO considering Dempsey was hurt by very small weak punchers.

 

Toney's counter right finds it's mark early on Dempsey from the outside, Dempsey in return decides to bore in and put his face right into the chest of Toney. He walks him to the ropes where is superior condition and much bigger punch pays dividends as he beats toney up over last 4 rounds for wide win.

 

The difference being that Firpo had the power to make it count.

 

I agree with foremansjab Dempsey would have been countered by Toney's RH Freddie roach said that James had a good right hand. Toney struggled against mcCallum. James weakness was fighters who come forward like Peters, Browne.
The best predictor was montell griffin an aggressive fighter who threw leaping left hooks like Dempsey beat Toney. Griffin was 5'7 to Dempsey's 6'2. Griffin style was fighting out of the crouch like Dempsey.