I'll vote for Jack, though I'm not 100% on that. He can merge with the city...there won't be much for Supes to punch or fry unless he tries to disintegrate the entire city. And Hawksmoor once used...what was it, Tokyo?...as a battle suit. So this is literally Superman vs. a pissed-off Mexico City. I'll take the world's largest city in that fight...though I wouldn't put it beyond Supes to just destroy it all and take the win.
-DM
Well Sups HAS shrugged off being force-fed the eletrical grid of Metropolis so we know he can stand up to a fight with a city.Theres also a chance the collateral damage could screw Jack over
If you REALLY wanna even up the match give him Metropolis.Huge population most celebrated city in the DCU AND brimming with Brainiacs tech.That should at leaqst have a better chance than that as American Dad put it "Gods blind spot" place