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Early on in the series, viewers learn that Uncle Jimmy was in business with Carmy's father and Lee Lane. James "Cicero" Kalinowski, more commonly referred to as Uncle Jimmy or Unc, is a Berzatto family friend. When he's first introduced in The Bear season 1, Uncle Jimmy explains that Carmy's late brother, Mikey Berzatto, owed Circero a lot of money. In total, Mikey's debt to Uncle Jimmy hovers around $300,000. Uncle Jimmy offers to buy The Original Beef of Chicagoland from Carmy, but the award-winning chef refuses, believing he can pay back his brother's loan.
In order to wipe out Mikey's debt, Carmy plans to transform The Beef into a fine-dining restaurant. However, that plan requires a ton of up-front costs. To fund the renovations, Carmy asks Cicero for another loan, bringing the grand Berzatto Family debt total up to a whopping $800,000. Although Cicero seems to believe in Carmy, Uncle Jimmy is also a very transactional person. If the restaurant fails, Uncle Jimmy gets the land. A business person to his core, Uncle Jimmy grew up with Carmy's father, though the two had a gnarly falling out 20 years ago.
In the same way that Richie is dubbed "cousin" by Carmy and his siblings, Cicero is given the "uncle" moniker as a way of referencing how close he is to the family. Although Uncle Jimmy seemingly isn't related to Carmy by blood, he's close in age to Carmy's father. In The Bear season 1, episode 4, "Dogs," Cicero says he misses Carmy's dad sometimes. A constant presence in the Berzatto children's lives, Uncle Jimmy is a more reliable person than their father — even if multiple members of The Bear's Berzatto Family tree owe him money.
You can see the connection between Carmy and Uncle Jimmy in the way they interact. Carmy seems to respect and even confide in Uncle Jimmy, despite the fact that their relationship is complicated by the financial debt. Uncle Jimmy, in turn, seems to genuinely care for Carmy, though his business interests sometimes clash with his personal feelings. Ultimately, their relationship is a nuanced one that adds depth to the story of The Bear.
While it isn't obvious where Uncle Jimmy gets his money, it is clear that he's Carmy's stand-in father figure in the wake of his biological dad's persistent absence. Throughout the series, Uncle Jimmy laments the fact that he wasn't around more often for the Berzatto kids when they were younger, especially during the incredibly harrowing Donna (Jamie Lee Curtis) and Mikey drama. However, Sydney (Ayo Edebiri) points out that he's here for the Berzattos now, which is more than Sugar (Abby Elliott) or Carmy's parents are doing. That alone cements Cicero's place as Carmy's father figure in The Bear.
Carmy, Mikey, and Sugar all have a different relationship with their father. Their father was absent for much of their lives, and this absence has left a lasting impact on each of them. Uncle Jimmy, in his own way, tried to fill that void, though he wasn't always successful. Despite the rocky past, Uncle Jimmy's presence in their lives is important, and he plays a significant role in their development. His connection to the Berzatto family, both through business and personal bonds, makes him a fascinating and complicated character in the show.