Obama Joke on Trump Running Guantánamo Into the Ground Getting Less Funny

President Barack Obama made Republican front-runner Donald Trump the butt of a few jokes on Saturday at his last White House Correspondents’ Dinner. “There’s one area where Donald’s experience could be invaluable — and that’s closing Guantánamo. Because Trump knows a thing or two about running waterfront properties into the ground,” Obama quipped, a reference to Trump’s Atlantic City bankruptcies.

But underlying Obama’s joke is the very real possibility that he will not be able to achieve his campaign promise to close the U.S. military detention center at Guantánamo Bay, Cuba — leaving it to whomever follows him into the White House. Obama’s chances of closing Gitmo have gotten a whole lot worse.

Last week, Sen. John McCain (R-Ariz.), the chairman of the Senate Armed Services Committee, effectively killed any hopes of working with the administration in the last annual defense policy bill under Obama. McCain vowed on the Senate floor to use the legislation to continue blocking the removal of any detainees to the United States. His House counterpart also passed a version of the bill, extending previous legislative obstacles in order to bar detainee transfers from Guantánamo and the use of any funds to close it until Obama is out of office. Presently, 80 detainees remain at Guantánamo, with 29 cleared for transfer to other countries.

As comedian Larry Wilmore underscored in his several jokes about Guantánamo during his roast, the joke may be on Obama. One of the biggest pledges of the Illinois senator’s 2008 campaign was to close the detention facility, whose extrajudicial limbo, he said, was at odds with American values. His inability to close it — due in large part to congressional opposition — has been a disappointment for many.

“You don’t see me going around presidentin’ all the time,” Wilmore said at the dinner. “I don’t go around passing health care, signing executive orders, pardoning turkeys … not closing Guantánamo.”

Later, he added, “I just got a note from the president saying that if you want another drink, you should order it now because the bar will be closing down. Of course, he said the same thing about Guantánamo, so you have at least another eight years.”

While Obama vowed to shutter Guantánamo and recently submitted to Congress a plan to close it — which Democratic presidential candidates Hillary Clinton and Vermont Sen. Bernie Sanders say they support — Republican candidates Trump and Texas Sen. Ted Cruz say they’d do the opposite. Not only have they vowed to keep it open, they’ve promised to expand it.

“Let me say this Mr. President: Don’t shut down Gitmo — expand it, and let’s have some new terrorists there,” Cruz said in late February as Obama made a historic visit to Cuba.

That same month, Trump said he would “load [Guantánamo] up with some bad dudes.” Trump has also promised to bring back torture, though its practice early on at Guantánamo, and at other military prisons and CIA black sites, rocked the Bush administration and severely damaged U.S. standing in the world.

“I said I think we absolutely need it, we should have it, and if we can, we should have worse,” Trump said of waterboarding last month, criticizing Cruz for being “weak” on torture and calling CIA Director John Brennan “ridiculous.”

Brennan said he wouldn’t allow torture, including waterboarding, even if a future president — say, a Commander in Chief Trump — ordered it.

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