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We are straight up in black swan territory for oil markets. Negative pricing on an expiring contract is one thing, a 50% fall in the primary WTI contract is another.

Its really hard to emphasize how unprecedented the situation is. The harder the crash, the worse the rebound
Regulators and even the mercantile exchanges need to seriously consider halting trading. The physical market oversupply may require massive global shut-ins and current trading dynamics could cause unimagineable futures prices
There is an outside chance the USO, which owns ~1/3 of June oil contracts, might liquidate. Today's price action even suggests they are already. Imagine what happens to prices at $10/barrel when 1/3 of the futures contracts are forced out. Yesterday's -$37/bbl might not be a low
As a quick aside, I feel for a lot of retail traders (i.e. people stuck at home trying to offset their stock market losses) that jumped into USO thinking oil had to rebound. Billions of their money went into USO in the last two weeks and its worth half now
Another challenge is that a lot of oil production is hedged at $20/barrel or above. These ultra low prices we are seeing are only acting to encourage the unhedged production from shutting in. If refiners/storage do not buy enough contracts, price may not halt production
Brent is different but it is also way down. US has some of the most global oil storage and, if it is full, a lot of the world's land-based storage is also potentially full/contracted. Brent may not face the risk of negative prices because it is seabound but <$10/bbl is possible
Re: the USO point, looks like they have indeed rolled over. That explains a lot of today's decline but also means short term volatility will continue
(Rolling over is not the same as liquidation as USO still has futures contracts but even the futures they largely shifted into, July, is down $7 versus $9 for June)
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