For one of the biggest automakers in history, Chrysler has one seriously complicated past. Founded in 1925, it was one of the three biggest manufacturers at the time, along with Ford and General Motors. The company teetered on the edge of bankruptcy a few times throughout its history, and in a $36 billion dollar deal, the (then-named) Daimler-Benz company bought Chrysler in 1998.

The merger had two primary goals: to increase the US market shares of Mercedes-Benz and to improve Chrysler vehicles with the expertise of Mercedes-Benz. The stocks did increase—but only for a few months. Due to a lack of cooperation and market forecasting, the merger began to fail miserably. Chrysler models weren’t selling, and by 2006, the company had lost $1.5 billion on top of axing 26,000 jobs.

Rather than being the modern-day Toyota/Lexus combo like everyone had hoped, the merger crashed and burned, ending with Daimler Chrysler selling 80% of Chrysler to the private equity firm Cerberus Capital Management for $7.4 billion. After economic crises, bankruptcy, and other mishaps, Fiat purchased Chrysler for $3.65 billion, creating what’s known today as Fiat Chrysler Automobiles.

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