Put forth a good case of Sailor Tom Sharkey beating prime Roy Jones Jr

Nope

 

If it's in Tom's era he wins, Roy may look alien compared to the time and might look real otherworldly for a few seconds but Sharkey will make this hideous and send ET home brutally via KO.

 

There isn't one.

 

No

 

He knock Jones out. You don't out box Jones. You back him up on the ropes and exchange punches. That's what Sharkey would do, and to be fair NO PED's for Jones.

 

Fight on a listing barge in a storm...

 

I need a good argument for Jones winning. Sharkey had pluck, an essential element which disappeared from our race in the 20th century, so much so that the word is now anachronistic.

Sharkey KO4.

 

He might hit his chin?

If that fails, then go to pressure.

 

Traditionalist nonsense. Thanks to modern science, pluck is easily available in pill form.

They are still working on panache, but that will come.

 

Well Tom Sharkey being a sailor he would have to.... ah forget it he has no chance.

 

He’d have to tackle Jones and hit him with repeated shoulders, head butts, forearm shivers, and low blows, and hope that the ref lets him get away with it.

 

Sharkey had the power to knockout Jones IF he connects at the right time and place. Weather or not he gets that chance is another story but it isn’t impossible.

 

Jones would have experience with that kind of dirty technique, and probably knows how to reciprocate in kind.

That said, your general strategy of forcing Jones to deal with unfamiliar roughness is probably the right one. I think late 19th century clinch wrestling fits what you're looking for.