Supposing Lennox Lewis had been with Emmanuel Steward from fight one?

his career would have gone more or less the same way. He still wouldn't be interested in anyone due to his even more boring fighting style, but maybe he would have avoided losing to McCall. Apart from that, everything is pretty much the same. He could have been wronged by the judges in a hypothetical fight against Tyson in 1996 in a clinch festival and a dirty fight. Perhaps Lewis and Steward would have gotten tired of each other earlier and wouldn't have lasted together until 2003.

 

Defeats mad man McCall but still loses to Rockman

 

I think his career would've been rushed and probably been worse.

Given how Emanuel Steward had a relationship with the WBO at that time, and a number of his fighters found themselves in WBO title fights very early in their careers in the late 80s/early 90s (veterans, too) ... like Michael Moorer (at light heavy), Leeonzer Barber, Tommy Hearns, Gerald McClellan, John David Jackson, Jimmy Paul ...

Lennox Lewis probably would've been fighting Francesco Damiani in 1990 or Ray Mercer in 1991 for the WBO heavyweight Title ... or maybe he'd have fought Bert Cooper for the vacant WBO belt when Mercer relinquished it.

If Lennox won the WBO belt, he wouldn't have been in the WBC ratings in Oct/Nov1992, when HBO decided to showcase the top four heavyweights - Ruddock-Lewis and Bowe-Holyfield. Moorer probably would've fought Ruddock instead.

Steward gets credit for his work with Lewis ... but there was nothing wrong with the way Lennox came up at the start of his career before the Ruddock fight. He fought all the right kinds of fighters.

Rushing Lennox and going the WBO route instead (and Steward had most of his top fighters go that route in the late 80s/early 90s) ... probably wouldn't have ended up BETTER.

Lewis wasn't wildly popular early in his career in the US or the UK (where fans didn't consider him a real Brit).

Winning the WBO belt, when it meant ZERO, and not being ranked by the other orgs ... or even worse losing to Mercer early on ... wouldn't have helped him on either side of the pond.