I love those 'good' assassin characters. Here's a trilogy about one. Go read it.

Update from my 2019 read/listen (first read it, then listened again).

I still loved this book 10 years later. I can see its weaknesses- it has some -but I still love the characters and this book is more about characters than anything else. Azoth/Kylar and Durzo are among my favorites even now. Even though it takes reading the whole trilogy to grok them (especially Durzo).

While I noticed all the beautiful details in the audio repeat, it became too harrowing to know every little failure in advance-and there is a lot of failure: failure to kill someone, failure to talk to someone, failure to listen to someone, failure to... everything. We had to stop the audiobook a number of times (listening to it on a road trip was a brilliant idea, reading it right before that not so much).

"The perfect killer has no friends only targets."

The official tagline of the book is wrong. Because our young protagonist Azoth is not just becoming any killer but a so-called wetboy and wetboys don't have targets but "deaders" because they are already dead they just don't know it yet.

Of course our protagonist has friends. Or where would the drama come from? And his teacher Durzo Blint isn't free from such bindings either.

Especially after rereading basically twice within a month and discussing with the non-nostalgic co-listener from the road trip, a reader might notice that there are a few instances where the plot stands on pretty thin ice mostly I find the timing with Vonda a bit too close and hard to believe that when Durzo and Azoth meet it has been just 4 months. Of course the timing is necessary for Vonda to be believably the mother of Durzo's daughter and for her to be young enough to be a deadweight in the plot

10 years is a long time in SF and since then the genre has made big strides. These days I would probably complain about Elene as too passive a character or Vi as too one-sided. But there is Momma K who rules her domain with an iron hand. The cast of female characters is varied if not perfect.

The magic system is not quite as brilliant as the one in the Lightbringer series. But rules and mystery balance each other well enough.

There is a ton of details that foreshadow later developments that one can only appreciate on a second read. It makes it absolutely worthwhile to reread this. Especially with Dorian's prophecy. Prophecy is hard to do well. But this particular prophet is fascinating and with a built-in weakness that makes him careful how much he can (ab-)use his gifts. And: he pays.

This book is long. And some parts of it are too long. The tension right in the middle of the book is such that one might think this were already the end and then comes the second half of the story of book 1. At the end the fight with Durzo and Kylar has so much fighting, parting, meeting again and starting over... that it starts to feel repetitive. Of course there is kind of an explanation for that my guess is that Durzo--who is kind of comitting suicide--has a hard time letting go after such a long live and that it takes him several attempts to finally make up his mind and maybe just maybe that is Kylar's final test... and maybe Durzo never really planned to let go until that scene in the tower and was so shocked that he might end up having "feelings"... but it does feel like being needlessly drawn-out.

Still for me this is one of the groundbreaking trilogies of the (very late) oughts that changed how I viewed the whole genre.

All in all I think it holds up pretty well but these days I'd recommend starting with Lightbringer.