  {\bf Abstract.} The present article is an essay about mathematical intuition
and Artificial intelligence (A.I.), followed by a guided excursion to a
well-known open problem. It has two objectives. The first is to reconcile the
way of thinking of a computer program as a sequence of mathematically defined
instructions with what we face nowadays with newer developments. The second and
major goal is to guide interested readers through the probabilistic intuition
behind Robbins' problem and to show why A.I., and in particular Deep Learning,
may contribute an essential part in its solution.
  This article contains no new mathematical results, and no implementation of
deep learning either. Nevertheless, we hope to find through its semi-historic
narrative style, with well-known examples and an easily accessible terminology,
the interest of mathematicians of different inclinations.
