Holmes vs. Bowe Lewis W. Klitschko V. Klitschko A prime Holmes stands a strong 6'3" (I think he was just a tad over 6'3" but less than 6'3 1/2"). His reach is 81". He weighs about 215Lbs. He was still solid at 220Lbs. His frame is big. He wouldn't look undersized vs. any of these men despite the "tale of the tape". Holmes had a solid chin and great recuperative powers. His stamina, hand speed, footwork, power, and ring generalship were all top notch. His jab was perhaps the best ever at HW. He wasn't a one shot KO artist but he had a strong jab and a solid right hand. He broke many good fighters down on way to stopping them in the mid-late rounds late. Bowe and Lewis are both 6'5" with 81" and 84" reaches respectively. Their best weights were between 235 and 245Lbs. The Klitschko's are 6'6 1/2" and 6'7 1/2" with 81" reaches. Their best weights are about 240-245Lbs. So, how does Holmes perform vs. these men?
With nowhere near disrespect to any of the opponents you mentioned, prime Holmes though maybe he would've lost, is definitely both tough enough and crafty enough to take a win over them all. I'm not saying ''old guy definitely beats these new guys with no problem" I'm saying the size difference would be negligible when all is said and done and I'd actually even favor Holmes in those matches. Against Bowe the most.
I think Holmes wins decisions vs. all of them. All tough fights though. I think Bowe gives him just as much trouble as anybody on the list.