He just came into the setup at a very wrong time. The right wing position was preceded by Darren Anderton, and then later by Becks. As long as Becks was holding onto that position, there was very little chance that he could play unless Becks couldn't play. I also think that he didn't play enough for Real Madrid to justify his selection over Becks or even Trevor Sinclair.
And back then, players were less versatile. I think of him as a strictly right winger and I don't remember his other roles being that memorable. Real preferred Guti to him as a central midfielder. I think they experimented him as a left winger to fill the ever-vacant spot for the England national spot but he did not cope well. If he were to play today, he would be asked to play a variety of roles at a young age and he would not have any issues being retrained as a left winger or right back.