yes a tough generation but nowhere near as tough as Murray faced. He faced a prime Nadal and a prime Fed for many years who are two goat candidates and an all time great in Djokovic who may still yet go down as a goat candidate although probably not. Also Hewitt didn't really face Nadal in his prime in the years, surfaces or business end of big tournaments that actually matter - that isn't trivial.
Hewitt failed to get high enough ranking points against the slow moving constant that is the field to be ranked high enough to face Fed in finals or semis consistently. He wasn't that good and was beaten consistently by the field. Something Murray can't be realistically accused of. Murray is clearly better. He tends to beat the field and then in general lose 3/4 of the time against the big three competition although that has changed in recent years.
I've no doubt Murray is better than Hewitt but this debate is about career. Personally I'd have Murray's for reasons outlines above but in terms of stats so far they're relatively even. With time though Murray is likely to change that although of course Djoko, Nadal and probably Del potro will have something to say about that.
What are you talking about? Hewitt got enough ranking points to be year end #1 twice, and to be ranked within the top 8 at year's end on three other occasions (2000, 2004 and 2005). The reason Hewitt hasn't gotten enough points to face Federer more often from 2004-2007 is because he declined immensely since 2004 or 2005. In 2005 Hewitt missed the French Open and the WTF due to injury and fell down a staircase just before the French Open that same year. In 2006 Hewitt's movement had already gone, so it isn't fair to compare them when Hewitt's prime years were probably 2000-2005. Hewitt was apart of Federer's generation but for the most part competed against Sampras' generation to start with, and he beat Sampras on grass when he was only 19 years old. Sampras was still a top 3 player at the time too, so wouldn't that be similar to Murray beating Federer in the Olympics final? Considering Sampras went on to win Wimbledon that same year.
And the hardest possible era? Are you kidding? Nadal wasn't around, Djokovic was his only legitimate opponent and he fought him to the bitter end in the US Open last year, Federer had already declined (and he is undefeated against Murray in slam finals) plus in this era someone who is a lesser player than Hewitt (Ferrer) made a slam final and several semifinals/quarterfinals. I think the numbers are extrapolated and made to seem bigger and more important. Yes, I agree that winning 8+ Masters is a great achievement, but that hardly comes close to two Year End #1's and two WTF titles.