Highest ranking of number 4 in the world in 2002 (from Wikipedia) and reached the semi final of every slam bar the Australian Open including a 4 time semi-finalist at Wimbledon. If Tsonga, Baghdatis, Soderling and Berdych can reach Slam finals in this era then I think Henman would have had a shot of doing so as well, although like those mentioned I don't think he would have won a final either. It would have been interesting to see Henman's serve and volley style against the baseliners of today. The likes of Stepanek and Llodra are the minority of today's era who serve and volley (and both are way past their prime) and I think Henman is a comfortably superior player to them both.