Never really noticed it before, but one of the recurrent themes in the opening chapter of The Fellowship of the Ring, “A Long Expected Party,” is that of Bilbo’s simultaneous wealth and generosity to the poor. A few passages:
[A]s Mr. Baggins was generous with his money, most people were willing to forgive him his oddities and his good fortune. He remained on visiting terms with his relatives (except, of course, the Sackville-Bagginses), and he had many devoted admirers among the hobbits of poor and unimportant families.
Even Bilbo’s cool relations with the Sackville-Bagginses implicitly corroborates the point: like Bilbo, they are comparatively wealthy; unlike Bilbo, however, they are greedy and covetous. Bilbo would rather spend his time and attention on the “poor and unimportant” than the rich and self-important. The enterprising Lotho Sackville-Baggins, of course, will be the one responsible for the Shire’s later enslavement to Saruman.
‘A very nice well-spoken gentlehobbit is Mr. Bilbo, as I’ve always said,’ the Gaffer declared. With perfect truth: for Bilbo was very polite to him, calling him ‘Master Hamfast’, and consulting him constantly upon the growing of vegetables…
A little later the Gaffer defends Bilbo as being “free with his money, and there seems no lack of it.” He further indicates that Bilbo is no less free with his time, condescending (as the Gaffer clearly views it) to tell his son Sam stories: ” ‘Elves and Dragons’ I says to him.’ Cabbages and potatoes are better for me and you. Don’t go getting mixed up in the business of your betters.’ ” And though the Gaffer is suspicious as to its value and long-term consequences, it’s with a hint of gratitude that he remarks that Bilbo has “learned [Sam] his letters.”
Finally, there is this passage indicating that, of those who were left gifts by Bilbo upon his sudden departure, the poor of Hobbiton received the best and most thoughtful attention:
Every one of the various parting gifts had labels, written out personally by Bilbo, and several had some point, or some joke. But, of course, most of the things were given where they would be wanted and welcome. The poorer hobbits, and especially those of Bagshot Row, did very well. Old Gaffer Gamgee got two sacks of potatoes, a new spade, a woollen waistcoat, and a bottle of ointment for creaking joints. Old Rory Brandybuck, in return for much hospitality, got a dozen bottles of Old Winyards: a strong red wine from the Southfarthing, and now quite mature, as it had been laid down by Bilbo’s father. Rory quite forgave Bilbo, and voted him a capital fellow after the first bottle.