The answer is; 'Yes, Bombadil deliberately and specifically choose those Barrows weapons given to the Hobbits'. It wasn't random.
By his own comments, he states explicitly that he knew what those blades were, who made them, what they were designed to do and what magic was woven into them. He also shows that he knew what the Hobbits were up to and where they were going. With that in mind he carefully picked through the weapons from the Barrow and selected those very specific blades to arm them with. He even told them what the blades were for. You can't get more clear than this.
De acordo com o universo de Tolkien, mais velho é considerado mais strong, mais sábio e mais poderoso e, segundo todos os relatos, Tom é o mais velho. Ele percorreu muito e largamente desde o começo até se limitar a uma pequena área não muito distante de Buckland.
But you are young and I am old. Eldest, that’s what I am. Mark my words, my friends: Tom was here before the river and the trees; Tom remembers the first raindrop and the first acorn. He made paths before the Big People, and saw the little People arriving. He was here before the Kings and the graves and the Barrow-wights. When the Elves passed westward, Tom was here already, before the seas were bent. He knew the dark under the stars when it was fearless – before the Dark Lord came from Outside.
Seu conhecimento da história e tradição da Terra Média também se estendeu por toda parte. Muito provavelmente superior a qualquer criatura viva como ele demonstrou enquanto conversava com os Hobbits sobre as lâminas da Westernesse. Ele lhes disse que as lâminas foram forjadas há muitos anos pelos Homens de Westernesse e que elas eram inimigas do Lorde das Trevas, mas foram vencidas pelo rei maligno de Carn Dûm na Terra de Angmar.
'Few now remember them,' Tom murmured, 'yet still some go wandering, sons of forgotten kings walking in loneliness, guarding from evil things folk that are heedless.'
Even Aragorn points out that the blades they were given were “wound about with spells for the bane of Mordor”.
Bombadil estava ciente do que os Hobbits estão fazendo, então ele os armou com as únicas armas deixadas no meio da Terra que os ajudariam nessa tarefa.
Ele estava realmente esperando os Hobbits e até havia preparado acomodações para eles:
In an understated way, Tolkien makes it clear that Tom’s meeting and rescue of the hobbits was not a chance encounter. Tom clearly expected the four hobbits—though we are not told how he knew they were coming. It’s clear that Tom expected them because, on the hobbits’ first night in his house, Tom takes them to their guest bedroom, opens the door—and there are four beds already made up and waiting for them, with a pair of slippers beside each bed. Even before their arrival, Tom had prepared a place for each hobbit.
Por estas ações sozinho, ele demonstra que ele está totalmente ciente do que está acontecendo fora do seu território auto-imposto. Ele também estava bem ciente do Um Anel, o que era, quem fez e por quê.
Then Tom suddenly commands, “Show me the precious Ring!” Frodo, to his astonishment, finds Tom’s command irresistible: he takes out the Ring and hands it over. Tom puts it on and nothing happens. He makes the ring disappear and laughs but then returns it to Frodo.
Frodo decides to play his own trick and puts the ring on his own finger. Although invisible to all the others, Bombadil says to Frodo, “Hey! Come Frodo, there! Where be you a-going? Old Tom Bombadil's not as blind as that yet. Take off your golden ring! Your hand's more fair without it”
Para ele, o ringue era feio e 'injusto'.
Em resumo; Bombadil obviamente desempenhou um papel ativo, embora deliberadamente passivo, em todos os eventos que se seguiram. Uma espécie de "ajudar sem ajudar", por assim dizer. Ele conscientemente deu-lhes as ferramentas necessárias para realizar sua tarefa, mas em última análise, deixou a eles para usar essas ferramentas para ser bem sucedido.