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Obadiah is Mr. Shandy's go-to guy. Like Susannah, he's got the Shandy family's secrets on lockdown. He tells Mr. Shandy what's going on up upstairs with Mrs. Shandy; he runs to get the doctor; he runs to get the doctor's instruments; he brings news of Bobby's death to the other servants in the kitchen; and he tells Mr. Shandy about the accident with the window via a train of communication: "Susannah, in passing by the kitchen, for fear of accidents, had left it in short-hand with the cook—the cook had told it with a commentary to Jonathan, and Jonathan to Obadiah; so that by the time my father had rung the bell half a dozen times, to know what was the matter above,—was Obadiah enabled to give him a particular account of it, just as it had happened" (5.26.2).
So, although we don't learn much about Obadiah as a person, he's got his fingers in a bunch of mud pies. He's someone you want on your side, because he could dish some serious dirt.