The recent wild swings in the prices of oil, metals and other commodities heightened worries that the volatility could spill over to broader markets as the war in Ukraine entered its 20th day.

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But risk in commodity trading has existed for a long time in the history of markets. The number of commodity trading houses has dwindled over the years, and firms that make money can be counted on on the fingers of both hands. Here is a list of some of the largest commodity firms that went bankrupt.

Phillip Brothers:

In 1990, the largest and most successful commodity trading house during its prime, folded after a shuffle in copper trading.

Metallgesellschaft AG: In 1993, their flawed hedging strategy led to a loss of $1.5 billion in heating oil and gasoline derivatives, which forced the company to shut down. Metallgesellschaft was a huge, German industrial conglomerate.

Amaranth Advisors: In 2006, the energy hedge fund, Amaranth Advisors, folded after losing over $6 billion on natural gas futures. The $9.5 billion hedge fund had lost almost 65 percent of its assets on a bet on the natural gas market.

BlueGold Capital: In 2012, one of the best-performing hedge funds closed its doors after shrinking from $2 billion to $1.2 billion due to failed crude oil bets. A large deviation from energy didn't pan out well for the firm.

Brevan Howard Asset Management: In 2014, one of the largest hedge funds globally, closed its $630 million commodity fund after consistent poor performance and low revenues.

Vermillion Asset Management: In 2015, private-equity firm Carlyle Group LP split with the founders of its Vermillion commodity hedge fund, which shrank from $2 billion to less than $50 million.

Phoenix Commodities Pvt Ltd: In 2020, Phoenix Commodities, a trader of agricultural products with offices in Dubai and Singapore, was liquidated after losing more than $400 million in potential trading losses.

Hin Leong: In 2021, one of Asia's largest oil traders, Hin Leong, closed its doors after failing to restructure $4 billion in debt. A crash in oil prices during the COVID-19 pandemic exposed the firm’s earlier financial troubles.