clueless, help me pick a wine for my boss

[graves17]

I need to pick a good wine for my boss as a gift, but I'm clueless about wine and he know quite a bit. I know he likes red wines, and he prefers a cabernet or cianti. He likes a bold taste, and he doesn't like California wines. My price range is about $25. Any suggestions so I don't get myself fired for makeing a bad wine choice =)?

[Innkeeper]

1998 Tenuta Friggiali, Rosso Di Montalcino, or a suitable substitute.