In Chapter 4, we learn this:
"Leonardo had trouble with deadlines". Over a three year period from 1478 to 1481, while living in Milan as a painter-artist, he received several commissions for significant works.... and did not get to DONE on any of them!
It appears he kept the down payment, but failed to collect the check that goes with DONE.
In fact, when it came to selecting the 1481 team to decorate the (new) Sistine Chapel, he got left off, allegedly because of his reputation for not getting DONE...to his consternation.
So, why wasn't Leonardo disposed to good project management? One of his supporters, who was also his critic, said this:
Alas! This man will do nothing at all, since he is thinking of the end before he has made a beginning. ... In his imagination, he frequently formed enterprises so difficult and so subtle that they could not be realized and worthily executed by human hands. His conceptions were varied to infinity
In other words, when came to the WBS, Da Vinci got trapped in the paralysis of analysis. He often began an engagement with a round of experimentation and investigation, sort of a 15th century version of Boehm's Spiral Method.
But we also see a measure of emergence and progressive elaboration in his inability to control scope or contain his imagination
In fact, containing (or constraining) imagination is the challenge in all "thought projects" (Thought projects: those which have intangible requirements, or requirements about intangibles) that have scope with no tangible boundaries and are simply what you can imagine.
I guess the good news is that Leonardo was able to get his game together and left the world with an incredible legacy. I think that's good news for all of us, even the agilists among us!