@Peggy8b thank you so much for your thoughtful reply! I really enjoy your pictures for reference. Your gardens are lovely and complement your gorgeous home so well.
I think we have a plan along the lines of your suggestion, and it's gonna be drastic. I think the holly is gonna go completely.
As the season has progressed there is more to this garden bed than I thought. There is honeysuckle in it! I wonder if that was planted. There is a seriously buried rosebush that is growing up in the weirdest way over the holly tree. It's going to be interesting to see what all is actually in that mess.