Family-Style Italian Sausages in Roasted Tomato Sauce

Last week, I had a few friends over for a family style dinner including my friend Dave who recently moved to Chicago. I wanted to make something that had a connection to his new city and to the unforgettable, family-style Italian dinners thrown by his grandfather… some of my earliest food memories. Growing up with Dave was great, because every so often he’d call me up and say, “hey… want to go eat at Pa’s”? It was one of the most exciting events of the year.

If you’re eating at Pa’s… you better bring your appetite because there is never any shortage of food. We would roll into his Italian Cantina, or private basement kitchen with six hungry guys, and he’d have enough to serve twenty. The entire industrial range would be swarmed with pots and pans, filled with homemade sauces that had been simmering for what seemed like days.

Platters of Italian cold cuts, antipasti, and freshly baked bread covered the giant oak table in the heart of the kitchen. The smell of his signature Amatriciana sauce catches your nose, he greets you with a smile and a hug, and instantly you feel like part of the family. Pa is an amazing cook but when I think back on the countless feasts I’ve endured in his kitchen, it’s not the amazing food that sticks out in my mind.


Rather, it’s his demeanor in the kitchen. He is an entertainer, and you can see it in his eyes, he truly loves having everyone around. His generous warmth and love for sitting down at the table and eating, laughing, and drinking together is so apparent. Pa’s Cantina is definitely where my love for cooking and entertaining developed. Being around family and friends and watching them eat and enjoy your food is one of the most rewarding feelings for me.

No wonder Pa would plop another bowling ball-size meatball on my plate, even after I loosened my belt. Now that Dave was stopping by, it was my chance to recreate that family-style dinner feel in my own kitchen.

It appears that Dave brought some of the windy city with him to Boston, because the monsoon-like conditions outside made a slow cooked meal sound even more enticing. When I think about Chicago cuisine, it’s all about the sausage. From Abe Froman, Sausage King of Chicago, to Upton Sinclair’s shocking novel, The Jungle, about the citys’ meat packing district.


I immediately ran over to the Butcher Shop in the South End to pick up a few links. The Butcher Shop makes their homemade sausage the old school way. They buy whole hogs, grind up the pork and spices, and pipe the mixture into the natural casings… absolutely delicious!

I love that they link the sausages together they way you’d see them hanging in a storefront in Italy, or toying with a dog in an old Tom & Jerry cartoon. I brought the links home and hung them from my kitchen cabinet where they dangled away like a savory wind chime. I wanted to keep everything whole, and rustic, all roasting away together in one pan so I didn’t do much to my ingredients.

I gave my roasted tomato sauce a simple base of garlic and shallots, which I smashed, and sliced. I set my oven to 350 degrees and the stage was set. I pulled out my giant roasting pan, big enough to fit a suckling pig, and gave the smashed cloves and sliced shallots a head start in the oven. I wanted to ensure that the sweetness of roasted garlic and caramelized shallots came through in my sauce. Once they obtained a rich caramel color to them, I tossed in three dozen vine ripe, cherry tomatoes that were about the size of a Titleist Pro V1.

Roasting whole tomatoes in the oven brings a whole new flavor to the ballgame. It’s so much different than making a sauce from a can because you’re using fresh tomatoes that pop, wilt, and stew in their own natural juices. When you throw in a few other simple ingredients, like shallots, garlic, and fresh herbs the result is comfort food at its finest.

After the tomatoes had popped and softened up, I took the pan from the oven and gently pressed down on them with my tongs, just to release the rest of the liquid. I placed the entire chain of links right into the roasting pan along with some fresh rosemary, oregano and thyme that I snipped from my garden. Back in the oven it went, where we could forget about it for an hour, giving us more time to catch up. The woodsy aromas of the fresh herbs and sweet garlic filled the kitchen as we poured some more wine and hung out over the stove. Typically, you wouldn’t think to use such strong herbs such as rosemary and oregano in a tomato sauce, but in this case, the dish is hearty and rustic. Save the basil for the delicate marinara sauce.

As the sausages roast in the bed of tomatoes, they release their flavorful pork fat drippings into the pan and add another element to the sauce. When the links were cooked through, I removed the pan one last time and finished the sauce with a healthy glug of 25 year old Balsamico. The syrupy vinegar adds more depth and sweetness as well as some striking acidity to help cut through the pork fat. I dumped the sauce onto a platter, and gave everyone a plate and a tear of chewy bread. The skins of the sausage were nice and crispy, perfectly encasing the moist, juicy meat. That signature “pop” of every bite made me smile. The sauce was packed with flavor, totally deserving an equally special wine.

I opened a bottle of 2004 Col D’Orcia Brunello di Montalcino, a wine that I have a special connection with. During my first trip to Italy in 2001, my family visited the small town of Montalcino and got a chance to swing by the hillside, Col D’Orcia estate. There we met with the winemaker, and got a tour of the facility followed by an amazing lunch on the back porch. We were privileged to be able to taste the highly acclaimed 1997 Brunellos before they were even released to the United States. Spending four hours at the table with my entire family, throughout a twelve course meal in the heart of Tuscany wasn’t a bad afternoon. Brunello translates to “nice dark one”, in the local dialect and is the unofficial clone of the Sangiovese grape. It is known as the King of Tuscany due to it’s complexity, power, and price tag.

Brunellos are often compared to the fine Pinot Noirs of Burgundy because of their smooth tannins, and ripe, fruit driven character. The wine is a deep ruby color, with loads of plum and raspberry fruit, impeccably balanced with slight nuances of oak. The tannins are so smooth, that the wine just rolls off your tongue as masterfully as the Italian language. The wine’s striking acidity makes it food friendly and inviting. As most great Tuscan wines do, this Brunello has faint aromas of cherries and fresh herbs, and a sneaky licorice taste on the finish. This mini family-style feast would make Snooki and the cast of the Jersey Shore jealous…. and the Brunello is far better than Ron-Ron Juice. We even had a slight “Situation” when I burnt my arm on the roasting pan, and I dropped my camera into the bubbling, hot sauce (thank God I bought the warranty). Just like in Pa’s Cantina, it wasn’t about the food we ate or the wine we drank, it was all about the great company we did it in.































































