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I'd say it was a mixture of underestimation and Lazy Boss Syndrome.
He underestimated the four hobbits in not realising what they'd be able to do before they came to the Shire.
Thereafter, he continued to underestimate all hobbitry, allocating the job of keeping order to his Ruffians. He thought they'd be able to handle it themselves without involving him.
That's how I see it.
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