Once the mysterious character "par excellence", Tom Bombadil has been so closedly analyzed by scholars and fans alike (as well as expunged from the more "mainstream" imaginarium) that a talk about him is at risk of either sounding naive or falling on deaf ears. Is there still something to be said about old Tom? By adopting a double-faced hermeneutical approach, i.e making use of Tolkien's epistolary without surrendering to the dogma of authorial exhaustiveness, I will try to place the character in the context of LOTR's contradictory approach to power: between Aragorn's journey to the throne of Gondor, and the Ring's allure, Tom Bombadil arises as an emissary of anarchy as well as a message of political hope amidst the unavoidable compromises that power requires. In an increasingly authoritarian political landscape, Tom Bombadil still offers us a chance to re-think our own relationship with authority, presenting us with the choice (and the cost) of getting out of society itself.