Ar4e4 we talking about the trumpet player as a musician or as an ''artist'' with everything that goes with it (=a vision for the entire band on how they should sound, the arrangements etc.).

If it's the latter, Miles is the obvious winner for me.

If it's the former however, I LOVE Lee Morgan; not so much his albums but his note-choices, tone etc. Anyway, as a musician, he is my favorite trumpeter.

Some other ones I dig:

Woody Shaw-VERY underrated; could play everything from straight hard bop to avantgarde and do it with style and personality. A lot of people dismissed him as a Freddie Hubbard-rip off but while Hubbard is more ''important'', I like Shaw more.

Lester Bowie (Art ensemble of chicago)-mostly known as an avant-garde trumpeter but unlike many other in that style, he had amazing technique and a knowledge of everything from the oldest New Orleans-jazz to 12-tone classical weirdness

Booker Little-Unfortunately, he died very young but a lot of people at the time supposedly thought he would be the next Clifford Brown and while he had that style, he was also a bit avant-garde and quirky. I love the records he did with Eric Dolphy and how he played there.

Bill Dixon-Another weird free-jazz guy who I don't think had the best technique but like Miles, he had great concepts and made very dark and moody music that's perfect for winters and autumns. Check out "Intents and purposes" or the many records he did on Soul Note in the 80's.

And obviously, I dig Dizzy and Clifford Brown and for some more obscure picks: Ted Curson (who played with Mingus) and Charles Tolliver (Jackie McLean and the Strata-east stuff) Hubbard too of course.

And Don Cherry was one sloppy motherfucker but he made a lot of great music and had tons of killer ideas and SOME of his solos with Ornette Coleman was actually extremely memorable (the one on "Congeniality"=wow!)
EDIT:I meant ''Chronology".