The Bear season 3 reveals new details about Uncle Jimmy’s potential income sources and his complicated financial situation, raising several questions surrounding how he got so rich and whether he will be able to fund Carmy’s restaurant. Although referred to as Uncle Jimmy, Oliver Platt’s character’s full name in The Bear is James “Cicero” Kalinowski. He was first introduced in The Bear season 3 as one of the closest people to the Berzatto family, who gave Mikey $300,000 to run The Original Beef of Chicagoland.

Even in The Bear season 2, Jimmy continues supporting the family by agreeing to become an investor in Carmy and Sydney’s new fine-dining venture. Season 3 shows how he puts some pressure on Carmy to make his restaurant more profitable, but still looks out for him and Sugar like they are his own children. Toward The Bear season 3’s ending, however, Uncle Jimmy’s arc takes a dark turn, hinting at how he may not be able to help Carmy in the next season.

Uncle Jimmy Has Made His Money Investing In Various Properties & Businesses

Real Estate Seems To Be Jimmy’s Primary Income Source

In many scenes from The Bear, Uncle Jimmy talks about real estate, loans, interest rates, and even the economy, suggesting that he has a real estate business. Perhaps in his early years, he put a lot of money into several properties and business ventures, which are now bringing him substantial returns. There is also a slight possibility that Jimmy has performed political “activities” at the grassroots level for a local party or cause. He has been doing this for a while and, in return, gets paid a hefty sum by the government authorities he supports.

Another possibility is that he might have retired from these political activities and is now enjoying the financial benefits of his past endeavors. He might have made some smart early investments in growing businesses and properties, allowing him to have enough money to not break a sweat before loaning $300,000 to Mikey. However, given how easily he arranges the liquid cash for Mikey to run The Original Beef of Chicagoland suggests that there may be more to his financial dealings than meets the eye. As many The Bear theories suggest, he seems to have his feet in somethin shady.

The Bear Hints That Uncle Jimmy Doesn’t Use Banks & May Avoid Paying Taxes

Uncle Jimmy Seemingly Has Other Illegal Sources Of Income

Towards the end of The Bear season 1, Carmy and the crew discover that Mikey hid Uncle Jimmy’s money inside tomato cans before his demise, hoping Carmy will eventually find them. When Carmy tells Jimmy he found Mikey’s loaned money in The Bear season 2’s opening arc, Jimmy sighs with relief when he learns Mikey did not deposit it in the bank. This suggests that Uncle Jimmy might have a lot of black money under his belt. It also hints that he might be evading taxes by not depositing a lot of his money in the bank.

The Bear season 3 reveals that Uncle Jimmy genuinely cares about the Berzatto siblings and is somewhat of a father figure for them after their biological father abandoned them. This highlights why he does not think twice before lending them money for their business ventures. However, Jimmy could also be laundering his own money by investing in the Berzatto family’s businesses. Since depositing large amounts of money in the bank can raise suspicion about an account holder’s profile, Uncle Jimmy might be using local businesses to whitewash his black money.

One Huge The Bear Theory Claims That Uncle Jimmy Has Mob Ties

Many The Bear Details Suggest Uncle Jimmy Is Involved In Some Shady Businesses

One fairly plausible theory also suggests Uncle Jimmy has mob ties. While the fact that he can arrange $300,000 in an instant alone raises suspicion about his criminal ties, The Bear season 2 also hints that he had some kind of “job” lined up for Richie but later kept him out of it. The Bear season 3 also reveals that Richie and Mikey used to drop some “packages” for Uncle Jimmy. Uncle Jimmy also manages to magically arrange permits and licenses required to run the restaurant, which makes it hard not to believe he has strong criminal or political connections.

In The Bear season 1’s episode 4, Carmy accidentally empties a bottle of Xanax in the cooler at a children’s birthday party. As a result, all the kids suddenly fall asleep in the playground. Carmy fears Uncle Jimmy will get mad at him for being careless, but Jimmy seems unbothered by the incident. While this could only be meant for comic relief, Uncle Jimmy’s nonchalant attitude toward such a potentially serious incident could be an indication of his day-to-day dealings.

The Bear‘s season 2’s iconic Christmas episode also features a scene in which Bob Odenkirk’s Uncle Lee asks Donna if she wants to get back into real estate. Since Lee is also a part of the KBL electric company, which was founded by Lee, Jimmy, and Carmy’s father, it would make sense if Lee and Jimmy collaboratively earned from real estate. However, as many other suspicious details surrounding Jimmy’s business dealings suggest, the real estate business might be the front for other illegal drug-related activities, which might even be linked with Mikey’s addiction and Carmy’s father’s sudden departure.

Did Uncle Jimmy Lose His Money In The Bear Season 3?

Uncle Jimmy’s Financial Situation Does Not Look Good After Season 3

Uncle Jimmy offers Carmy a deal in The Bear season 3’s episode 9: if the restaurant gets a positive rating from the Chicago Tribune, he will continue funding it, but if it does not, he will have to pull the plug. When he returns to his car after this interaction, Computer asks him whether he told Carmy the truth about his financial state. The scene suggests Uncle Jimmy’s business has also taken a major hit from the post-pandemic economic downturn. He is not as well-off as he used to be and may not be able to fund The Bear restaurant in the future.

When Jimmy confronts Computer, the financial advisor jokingly warns him that he may not be able to afford him soon and even says it is probably better for him to “experience what it’s like to be poor.” Although Jimmy promises Carmy that he will continue funding them if they get a good rating, his financial situation suggests he will struggle to uphold his word. While only time will tell how the central restaurant may stay afloat in The Bear season 4, Uncle Jimmy could get Carmy involved in his illegal activities to secure the necessary funds. Or, Uncle Lee might step in as The Bear’s ultimate savior.