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Since March 1962, the debt ceiling has been raised 74 times, according to the Congressional Research Service. Ten of those times have occurred since 2001. Expect more of the same over the next decade.
Back in November 2004, the last time the debt ceiling was about to be breached, the Treasury Department did everything it could (and then some) to avoid breaking through it. Congress quickly passed the necessary legislation allowing for an additional $800 billion debt so the debt ceiling was not breached.