Mr. Shepherd is a "civil, cautious lawyer," Jane Austen explains in her novel Persuasion, and he serves Sir Walter Elliot, a widower who finds himself deeply in debt. Mr. Shepherd is shrewd as a counselor: he defers to Mr. Elliot's neighbor, Lady Russell, to advise him as to the best means of reducing his debt. And Mr. Shepherd carefully prods Sir Elliot to lease his estate to a naval officer, highlighting the attractive qualities of such men and emphasizing the pitfalls of alternatives. It is an excellent display of the art of persuading a recalcitrant client.

Mr. Shepherd's motives, however, are not wholly pure. He foists his once-married daughter, Mrs. Clay, upon the Elliots in the hope that she would gain the confidence Sir Elliot's eldest daughter and perhaps even wed Sir Elliot himself. As Sir Elliot has only daughters, it would jeopardize their estate if he remarried and had a son. And it would ensure that Mr. Shepherd's interests, not Sir Elliot's, were paramount in these considerations. Mr. Shepherd calls into question whether he is truly serving his client's interests, or merely serving his own.

He may not be a paragon of virtue, but his sly role as an attorney is notable, underdiscussed, and good enough for the Fictional Attorney of the Month.