Making text fall behind multiple objects (track mattes)

So I have a drone shot traveling backwards over some trees and the word Iceland looks like it is sitting between the trees. The good news is, I was able to get the words to go behind one of the two objects, I just could get it to only go behind one tree at a time. I can even get the track matte to switch between the two objects but never both at the same time.

Please see the attached image for reference, this will help greatly in understanding my problem I think.

Perhaps there is a better way to achieve what I am trying to do? Perhaps I do not understand how to use track mattes in the best manner? Any help would be greatly appreciated!

If you cannot read the text in the comp details in the bottom left, please let me know, I'm new here and not exactly sure what things will be most helpful to the pros to get a good understanding of how to help me with this issue.

THANKS!