This discussion made me wonder about how trumpet player Joe Gordon and tenor man Harold Land fit with Monk, so I pulled the CD and listened to it.
In my view Joe Gordon works very well with Monk. His solos are thoughtful and relates well to the tune being performed.
Harold Land surprised me by sounding highly influenced by Charlie Rouse, who also solos on the session. Land's sound and approach is, to my ers, very Rouse-like.
Had Joe Gordon and/or Harold Land worked for a lengthy period with Monk, I suspect they would have turned out to be terrific colleagues. The album on which they appear with Thelonious was a one off, which in such a sort time I found highly enjoyable. "Thelonious Monk Plus Two at the Blackhawk".