Perhaps the novel's most controversial depiction because of the blatantly anti-Semitic descriptions employed by Wharton to describe him, Simon Rosedale is nevertheless a fully realized character with both admirable and despicable qualities. Possessing enormous wealth and the potential to possess far more, he desires to marry Lily in order to expedite his entry into New York society. He continuously pledges his love for Lily, but also realizes that Lily has become a social liability. He offers her a solution — publicizing love letters from Bertha to Selden — albeit one that Lily cannot bring herself to enact: first, out of fear of exposing Selden's dalliance and, second, out of her revulsion to blackmail. The transaction by which Lily acquires the letters in the first place is most likely arranged by Rosedale, as he later indicates to Lily that he knows she possesses the letters. Rosedale subsequently offers to repay the money Lily owes Trenor, but Lily refuses on the grounds that a similar offer from Trenor got her into trouble in the first place.