Well Gandalf must have notcied the lack of Boromir, and he hadn't spoken to Merry or Pippin, so he had many reasosn to think that (a) Boromir and Sam went a different route, (b) 1 or more of those 2 are dead, or (c) Boromir's gone, and Sam's been captured (possibly taken by Mordor Orks when they argued with Sartuman's ones), etc.
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