I designed 20 of the Richard Stark (Parker) novels for the University of Chicago Press and they asked me to design the Grofield ones as well - The Dame, The Damsel, Blackbird and Lemons Never Lie. The 4 Alan Grofield novels work in tandem with the Parker novels.They wanted a visual connection to the first series but also wanted them to stand on their own.
The author suggested the idea of a double umbrella which is alluded to in the book. I must have spent my entire Saturday trying an assortment of umbrellas with different rain effects but couldn't get the right tone for this book on Dante and medieval culture. The one with the black background was where I arrived at the end of the day - kind of static and lifeless. After putting it aside for the rest of the weekend I gave another stab at it this morning in the style of Leonardo's sketches.