The Republic National Distributing Company filed for Chapter 11 bankruptcy on Sunday, signaling the end of what was once America’s second-largest alcohol distributor. In its filing, RNDC reported between $500 million and $1 billion in assets and $1 billion to $10 billion in liabilities. The company’s largest unsecured debt is $93.9 million to Proximo Spirits, the distributor of Jose Cuervo tequila and Proper No. Formed in 2007 through the merger of Republic Beverage Company and National Distributing Company, the firm was responsible for an estimated $12 billion in annual revenue at its peak. Insiders speculate that RNDC may have overleveraged itself, accruing hundreds of millions in debt as it pursued an aggressive westward expansion plan.