Chet Baker vs. Miles Davis

Even though Chet Baker has a couple of golden horn awards, I always thought that they let him play the trumpet so he would sing especially in the later years when he was reported to have problems. I'm a big fan of his singing but not so much his horn playing. So if you are asking about playing.... Miles Davis.... 

Chet Baker, to me, was a pleasant crooner a good trumpet player. On the other hand, I believe Miles Davis was a musical pioneer who evolved with and at times defined what jazz was to become.

I really like Chet as well.

If you like Chet’s playing, try Kenny Dorham’s “Quiet Kenny”.  It’s superb late night jazz listening. 
 

If you like mellowness in the genre, try Curtis Fuller’s early work, like “Bluesette”.  

“For trumpet playing I'd say Clifford Brown>Miles Davis>Lee Morgan>Freddie Hubbard>Dizzy Gillespie and then Chet Baker.”

@jond 

I would also add Chris Botti in this conversation…Botti's passion for the trumpet was ignited when he heard Davis play "My Funny Valentine" at age 12. I enjoy Botti’s work just as much as other guys on your list.