This tasting was exercise for sure. And, it was an unusual one.  

These Umberto Cesari wines are tiring. They don't taste at all of Sangiovese and less yet of Sangiovese di Romagna. At least, they are ambitious; they are concentrated with decent finishes and taste of (very) new oak. They both need a vigorous decanting (I used my WinePrO2) to even consider approaching now. These wines need food.

87
Umberto Cesari 2013 Resultum Sangiovese Rubicone IGT 14% $100
Showing a wee tinge of Sangiovese orange at the rim, this seven-year-old wine's bouquet is moving into tertiary characteristics, too. There is a distinctive singed orange peel aroma coupled with açai, spearmint and amaro botanicals. Full-bodied, this wine makes a sweet-sour impression with a creamy attack that beelines to the back palate with aggressive acidity and searing tannins. While the finish has some length, it is mostly of dried fruits (it tastes as if it was made with dried grapes) and stale, ground cinnamon. Additionally, I am confused by the price point given the moderate quality character of the wine. At least the alcohol is well-balanced and the cleansing acidity helps to relieve the dryness on the finish.  

86
Umberto Cesari 2017 Sangiovese Riserva 13.5% $22
This is an unusually dark Sangiovese. There are even purple and black influences at the core - not Sangiovese colors. It's astonishing that this is a varietal wine. It also doesn't smell much like wine but rather of a bakery with its cocoa powder, candied plums (very much like a French pâte de fruit) and vanilla bean. This certainly is a candidate for a "red wine with chocolate pairing". However, I suggest dark rather than milk chocolate as, similar to bar chocolate with a high percentage of cocoa beans, this wine is very granular in texture thanks to its splintery, saliva-wicking tannins. It does have bright acidic relief, but the incredible, biting dryness takes over the entire palate impression very quickly. If there weren't such impressive concentration, I would not have managed an 86 for this wine.