While its easy to see with hindsight that the operation wasnt going to work, at the time that wasnt the case. Yes it was a very ambitious plan, and there were a number of big risks to be taken, but thats the way with large military operations.
I have read Band of brothers, and its clear that the author didnt like the plan, and personally disapproved of it. His condemnation of the operation seemed to stem not because of its military merits but largely because he just didnt like it. There is also a point that some of the blame of the failure could rest with the 82nd airborne as they failed to take several vital bridges when they were supposed to, allowing time for the defenders to dig in, and meaning that 30 corps had to help them take territory that was supposed to be open and waiting for them. Whether this also played a part in Winters writing, being a member of the 82nd, is impossible to say.
Fact is that the operation came very VERY close to succeeding despite all the mistakes and unforseen problems.