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If I skim correctly only one book has been so much as runner-up for both the Caldecott Medal and the Geisel Award. First the Egg written and illustrated by Laura Vaccaro Seeger was runner-up for both in 2008.
The history isn't long, only eight years for the Geisel Award through 2013, but that record now comprises 33 Caldecott winners and honor books.
Would most of these books be eligible for the Caldecott Medal, as children's "picture books", or do such books fare poorly here?
Beside satisfying curiosity and categories, this concerns Geisel's legacy. He was a cartoonist and a writer-illustrator of children's books that would all be deemed picture books, as far as I know. But he was also a publisher of books for beginning readers presumably including many whose text is primary with illustrations secondary.