It was a stupid move. Few people benefit from increased drilling, mainly wealthy oil executives and large investment groups that own much of their stock. (The amount each individual who has a pension gets from their increased profits is so small it's laughable to call that a benefit.) The workers get a benefit, but one that could be far better. US oil workers are significantly more likely to die on oil rigs than foreign oil workers because we have the loosest safety regulations in the world.
If Obama wanted to increase drilling (which I don't really support, but don't 100% oppose), he could have at least used it as a bargaining chip to get agreements on ending the oil tax subsidies, improving safety regulations, and (the only short-term policy that has a shot at lowering prices) reinstating the commodities trade regulations that were removed in 2000 before oil prices started to rise and volatility dramatically increased.
Obama has a frustrating habit of giving the Republicans everything they ask for and then negotiating from there even further to the right. He is great at arguing, but terrible at negotiating. Unfortunately, he doesn't govern towards his strength.