I don't think it's unreasonable as such that there's a bit of quality wise difference between the Legacy players. That's rub of the green, etc. Same with the DoF players. You can luck out and get Beckenbauer - or be dealt a relatively shitty hand compared to that immense standard. Part of the game, that - and we all get four rounds to get lucky/unlucky in, so it should even out.
The gap can't be too big, though - that's obvious. Now, quality wise I don't think you can claim that Kuyt sticks out like a sore thumb. He does bring plenty of useful qualities to the table. With him it's more the danger that voters could be downright prejudiced against him - which is obviously a huge disadvantage for his manager. To what extent the latter is true when it comes to the people who actually vote in these things, is another matter. As suggested above, the Liverpool factor isn't that crucial in drafts.