The only way we'll ever know is to invent the Infinite Improbability machine and give it a really hot cup of tea with which to run its calculations from.
I suspect not.
Considering they would have traded all their Leicas in to cliveh at one banana each before they could find out how to use them.
The puddle jumper photo became iconic because of who shot it, not because it was revolutionary, uniquely aesthetic, or even technically excellent. It came to represent HCB's lifetime of work at snapping the decisive moment.
So, no, an infinite number of Leica-carrying monkeys cannot reproduce it because they aren't HCB. There are already millions of "puddle jumper" photos out there from millions of unknown photographers and they are destined to remain unknown. To produce another "puddle jumper" photo, a photographer needs to establish a body of work recognized as unique or seminal. From that work, a "puddle jumper" photo can emerge as a representative icon.
Actually Clive, if you let loose an infinite number of monkeys, I suspect all their photos would be mostly of other monkeys...