The seal on the US Treasury building in Washington, DC.

As the U.S. economy crumbled in early 2009, President Barack Obama offered a plan that he said would save American jobs: A crackdown on corporate tax loopholes that encourage companies to send profits abroad to avoid paying billions of dollars in U.S. taxes each year.

Tax lobbyist Ken Kies was not worried. A decade earlier, he had led a fight to preserve a key loophole— known in Treasury Department shorthand as the "check the box" rule—when another Democratic president, Bill Clinton, had tried to kill it.