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Jack's advantages are much better mobility, much higher intelligence and a wider arsenal of both close and long range weapons. Michael's advantages are better stealth and his immortality. Michael has higher Ap but it isnt a big enough difference to really matter especially since they both use piercing attacks primeraly

Overall i think Jack can pull the W with enoguh time. Using his wires and grappling hook to move around and evade micheal while spamming knives from a distance is something Michael doesnt really have an answer. The biggest issue is the immortality but knife spam + cutting off his limbs with the wires should do enough damage to incap Michael.
 
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Jack, michael immortality and superior strenght may give him a chance but once Jack realizes it he will find a way to defeat michael(either by incapacitating michael or cutting off his head)
 
Jack FRA via being a better fighter and tactician.

Also, I'm sure that Jack's enhanced senses & extrasensory perception should negate Michael's attempt to ambush him.
 
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