Given this thread has a "popularity" theme this
match is a tough call. Even Maedhros is in a sense
a forerunner of Thief Baggins in trying to "steal" two silmarils
since the sons of Feanor had forfeited a legitimate call on
them.(Yes, everyone tries to steal from poor Smaug, Gollum,
and Sauron).
But Maedros' flaws are more deep rooted then Frodo's Uncle
and Bilbo (other then his shocking animus towards
noble dragons) has more of an ability to not just want to be
generous and show magnanimity but to actually do so, so
+ + Bilbo, a.k.a. Thief Baggins