Characters/Pairing: Sam Gamgee
Book/Source: Lord of the Rings
Disclaimer: Tolkien's the genius, not me.
The first thing Frodo did as Mayor was have the Lockholes cleaned of everything resembling a prison. And then they sat empty, no one wanting to have much to do with them or the memories they conjured, poor Will Whitfoot least of all.
When Sam was elected, he had them turned to wine cellars. Not only were the vinyards of the Shire doing increasingly well, but also the lands to the east. Ruby red Dorwinion, and sweet wines from Lossanarch were soon popular everywhere.
No one believed him, though, when he said they drank like Elvenkings in the Green Dragon.