Terrible Tim as he was, against the heavies of the late 1890's and early 1900's, 20 rd fights old time gloves how does he fare against the following? Fitzsimmons Ruhlin Corbett Jeffries Choynski Maher Sharkey
with his lack of conditioning, those body shots might take him down quick. if not, then by round 15 he'd be cooked.
It's extremely hard to say because how can anyone know how he'd adjust to the conditions of the era? However, in my mind, putting a Witherspoon (a talented, big, skilled man who can punch) against the likes of Corbett, Fitz, Sharkey & Choynski, all much, much smaller fighters, seems almost sadistic. Assuming that Spoon could adapt to the conditions of the times, that is.