Chet Baker vs. Miles Davis

Of course, I like them both! (Surprise).

 But, as others have pointed out- listen to Clifford Brown. Sweet tone, expressive, feel, nuance, articulation. Control of his instrument.  Many of his recordings are not great (like Monk's recordings) but, he played like a sweet, cool breeze on a hot summer day.

As two others implied, really apples and oranges. Chet was the quintessential representative of theWest coast sound, and Miles (and Dizzy) was the leader of the East coast sound in the 50's. The two schools of jazz are so different they really stand on their own.

BTW, Miles started on the West coast and actually played on stage with Chet. Look for album "Miles Davis and the Lighthouse All-stars" from 1953 in Hermosa Beach.

Also, Chet was always very respectful of Miles, while Miles denigrated Chet. Miles publicly saying that Chet ripped off his sound, as strange as that sounds....

GAR

It’s like the scene in “Diner”, where they debate the relative merits of Sinatra vs. Johnny Mathis.  Like Sinatra, Miles is in a different league from Baker.  But like Mathis, it’s ok if you prefer to make out to Chet.

I love Trumpet players. I think Chet was smooth and appealing but Miles was a musical force. Miles had a broader range of outstanding work and is one of the absolute greats. This should not mean that Chet was not special.

In some ways, its kind of like comparing Jimi Hendrix and Stevie Ray Vaughan. I like them both, but Stevie would not have been Stevie without the presence and direction of Jimi Hendrix.... 

It was said before, its a preference but I celebrate all these artists.

Without discounting either's contributions to the jazz canon, I'd go with Woody Shaw for both performance and compositional chops.

Jim