But Obama, an idealist at home, has turned out to be more cold-blooded than most recent presidents about the tough choices to be made in the world, downgrading democracy and human rights accordingly.

From Syria to Ukraine, Egypt to Venezuela, this president has shied away from the pay-any-price, bear-any-burden global ambitions of his predecessors, preferring quiet diplomacy to the bully pulpit—when he is engaged at all.

He has his reasons.

A decade of occupying Iraq and Afghanistan soured Americans on George W. Bush’s “freedom agenda,” taking invasion off the table as a policy tool. And there are broader global forces at work too: the meteoric rise of China, new tools for repressing dissent, the malign effect of high oil prices.

Freedom in the world has declined for 8 straight years, according to Freedom House—not just under Obama.

But if the president is troubled by these trends, he shows few signs of it. “We live in a world of imperfect choices,” Obama shrugged last year—and his administration has made many, currying favor with a rogue’s gallery of tyrants and autocrats.

Here, Politico Magazine has assembled a list of America’s 25 most awkward friends and allies, from Pakistan to Saudi Arabia, Honduras to Uzbekistan—and put together a damning, revelatory collection of reports on the following pages about the “imperfect choices” the United States has made in each. “I will not pretend that some short-term tradeoffs do not exist,” Rice admitted. Neither will we.

1. Pakistan

America’s worst ally—being home to Osama bin Laden will do that to your reputation—Pakistan has gobbled up billions of dollars in U.S. aid and “reimbursements” for services rendered in the war on terror.

And while Pakistan’s powerful military and spy services have often collaborated with their American counterparts on drone strikes and militant arrests, they’ve just as often made mischief, hosting the Taliban and other extremist groups, planting false anti-American stories in the press and undermining the civilian government.

“The cancer is in Pakistan,” Obama reportedly told his staff in 2009—but he has yet to figure out how to excise it.

2. Saudi Arabia

Ever since 1945, when President Franklin D. Roosevelt huddled with King Saud bin Abdulaziz for five awkward hours on a U.S. warship, the United States has had uncomfortably intimate relations with Saudi Arabia.

Seventy years later, the two countries are trapped in a loveless marriage. No country buys more U.S. weapons than the autocratic, oil-rich Persian Gulf monarchy, and no country—with its obscurantist interpretation of Islam, medieval punishments and harsh treatment of women—makes for a more embarrassing U.S. ally.

But the relationship is in increasing need of counseling as the Saudis grow exasperated with U.S. policies in the Middle East, especially in Syria, and threaten to find other partners. As the Saudi foreign minister put it, “It’s a Muslim marriage, not a Catholic marriage.”

3. Afghanistan

Bribery, embezzlement, corruption. And that’s just on the part of America’s partners in Afghanistan.

As the United States prepares to wind down its 13-year war on the unforgiving Afghan plains and craggy mountain hideaways, it has given up on almost any pretense of nation-building in a country where President George W. Bush once promised to help build a “free and stable democracy.”

The United States is even, it turns out, giving tens of millions of dollars in cash directly from the CIA to Hamid Karzai, the mercurial tribal leader it installed as president in 2001. Sure, there have been lectures about good governance and reams of reports tsk-tsking over the colossal waste, fraud and abuse of the roughly $100 billion in U.S. aid and reconstruction money that has flowed into Afghan coffers, but little has changed, and the United States has basically stopped trying.

Standing next to Karzai last year, Obama summed up America’s diminished expectations, asking, “Have we achieved everything that some might have imagined us achieving in the best of scenarios? Probably not.”

4. Iraq

In November 2013, President Obama praised Iraq Prime Minister Nouri al-Maliki for “ensuring a strong, prosperous, inclusive and democratic Iraq.”

One has to wonder just which Maliki—and which Iraq—Obama was talking about. Since his selection in 2006, Maliki has consolidated power to the point where many alienated Sunnis call him the “Shiite Saddam,” while the country has exploded anew with sectarian violence that killed more than 8,000 people in 2013.

Just weeks after Maliki’s visit to the White House, al Qaeda was taking over large swaths of Fallujah and Ramadi, two cities where American forces had fought pitched battles in the streets.

Never mind that the United States has sold Iraq some $14 billion in military hardware since 2005 and quietly left behind dozens of military and CIA advisers since its 2011 pullout—the spillover from Syria’s civil war has proven too much for the Iraqis to handle. And in more ways than one: U.S. officials also accuse Maliki’s government of looking the other way as its close neighbor, Iran, supplies the murderous Syrian regime with cash, weapons and advisers.

5. Egypt

Coup or no coup, the United States still showers the Arab world’s most populous state with $1.3 billion in military aid each year—a tradition owing to Egypt’s strategic position astride the Suez Canal and next door to Israel.

Since haranguing Egypt’s longtime dictator, Hosni Mubarak, to step down “now” in February 2011 amid the inspiring protests in Cairo’s Tahrir Square, the Obama administration has largely been reduced to hand-wringing as the men in khaki reclaimed power, killing hundreds of Islamist protesters along the way.

6. Equatorial Guinea

 Teodoro Obiang Nguema Mbasogo—who claims, “There is total freedom of expression, there has never been repression” in his country—is in fact a famously corrupt thug; after toppling his own uncle in 1979 to seize power in Equatorial Guinea, he has amassed a fortune estimated at several hundred million dollars, while more than three-quarters of Equatorial Guineans live in abject squalor and outright repression.

Washington has also cashed in on the tiny country’s massive if ill-distributed wealth, with American lobbyists, defense contractors and banks variously taking on Obiang as a client during his more than 34 years of strongman rule. In 1995, the United States shuttered its embassy in Malabo after threats to the life of the U.S. ambassador, an outspoken human rights defender.

A 1999 State Department report found that Obiang’s sadistic security forces had, among other horrors, rubbed prisoners’ bodies with grease to attract stinging ants. But no matter: In 2003, the United States agreed to reopen the embassy, and Secretary of State Condoleezza Rice later warmly welcomed Obiang to Washington as a “good friend.”

Even President Obama has posed for a photo op with the dictator, who once won reelection with 103 percent of the vote in some precincts. Why all the love? Equatorial Guinea’s $9 billion oil and gas bonanza, almost all of it produced by U.S. companies, has made it one of the largest destinations for U.S. investment in Africa, and much of that oil, naturally, finds its way across the Atlantic.