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In my opinion, after Saul tried to kill not only David, but also even his own son Jonathan because of Jonathan's friendship with David, Jonathan suspected that Saul was keeping him (Jonathan) under constant surveillance -- even through Jonathan's own servant -- in order to keep Jonathan from meeting (and, in Saul's view, conspiring) with David. Jonathan therefore had to devise a credible pretextual means of communicating with David that would remove the servant from the situation, and also not arouse the servant's suspicions.
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