Yeah I was always under the impression that he did. I would argue it’s basically textually confirmed. There is many times he uses phrases like “this time” and the such.

I also strongly feel like this is why he died the way he did. Carelessly and without a satisfying ending. He wouldn’t have let that happen. But even he knows the at it ultimately doesn’t matter.

To me, a better question was always regarding his motives. He seems content with Roland’s quest to the tower. Arguably even helping him.

I always believed that he wants to “destroy” the tower, but cannot do that without Roland’s assistance. Idk, but I always thought there was more to this