i have to admit I did not see Leo's death coming but absolutely saw Matt Damon's as well as Damon's "partner".
So I rewatched it again last night. I had not seen Leo's death coming either, but my problem with it is that IMO it violates the writer's compact with the audience and their "willing suspension of disbelief," which is to say, nothing in the movie to that point indicated that that otherwise nothing character was a mole, until BLAM, then "hey, I'm a mole too!" Bah, that is no way to kill off the main character.
Relatedly, and maybe I missed it, but why did Marky Mark shoot Damon? Was there any indication that he was tied to something?
So basically the two lead characters are killed off in crappy ways.
Otherwise it was OK, better than I had remembered but still somewhat disjointed. The way Leo became an undercover cop was unbelievable; they could have handled that better. Similar for Damon whooshing right into the special plain-clothes unit. Maybe it is just Damon movies (thinking Good Will Hunting) but I never buy the love interest. I also didn't like the casting in that Damon and Leo look similar enough that for a while I was like "OK, that's Damon, he's the mole cop, right?"
The Boston accents have already been covered.
Still, it moved quickly and was engaging. I'll give it 4 Jerry stars.