Lennox had more fighter's instincts but Wlad was technically better. Lewis would be best served by turning it into a brawl. If he tried to box Wlad I think he'd come unstuck. I pick Wlad, but, it should be no surprise if Lewis won.
So a 220lbs, 20 year old Wlad vs a 230lbs, 23 year old Lewis. I'd pick Lewis, those 3 extra years and the extra 10lbs would be an advantage. He'd be too strong, have that reach advantage too and with Wlad's tendency to stand in front of his opponents after throwing, he'd get caught once Lewis steps on the gas.
Klitschko W. has had problems with technical boxers of his size (Fury, Joshua). He would have had even with Lewis.
OK, re-stating my prediction. The OP is being sneaky He'd comparing the greenest version of Lewis to the greenest version of Klitschko. Didn't notice that. So, who was the better boxer at the start of their pro careers? While I feel Lewis ended up with the better resume at the end, I also feel Wlad was much the more complete boxer at the start of his career. Lewis developed greatly as he went along. I have little hesitation in picking green Klitschko over green Lewis.
OK, youre right. As to Lewis of 1988 I dont have sufficient information to answer but imo Lewis from Bruno (1993) to Vitali would put all Wlads versions in serious troubles.
Lewis would have given any heavyweight in history serious troubles. As I said, I'd pick Wlad even prime for prime - but there's not much in it. There's totally an argument to be made favouring Lewis, too.