Meet Barack Obama's Frenemy: Democratic Senator Bob Menendez

Just across the Hudson River from Manhattan lies Union City, New Jersey. With 68,000 citizens it's gritty, working class and a beautiful piece of Americana. For decades it had the largest concentration of Cuban-Americans outside of Miami. Some came to the town before the Cuban revolution in 1959 that put Fidel Castro and his Marxist government firmly in power. Others came during different migrations—the flood after Castro clamped down on personal and property rights in the early '60s, and in the 1980 Mariel boatlift. Each brought drive, determination, profoundly anti-communist views and a belief in American power.

Robert Menendez was born in Union City to parents who left Cuba pre-Castro and until recently, when he moved to more suburban Bergen County, he lived there his whole life, winning his first election at 20. So rough were the city's politics that he testified against the mayor he had worked for. Menendez himself faced a corruption investigation in 2006 by then-U.S. Attorney Chris Christie. It fizzled, as did another regarding donors, the seeds of which Menendez allies have speculated might have been planted by the Cubans—which sounds simultaneously crazy and plausible. Despite the city's anti-communist spirit, Menendez stayed a Democrat on social issues and in party affiliation. His hawkish views were to the right of his party even when he came to the U.S. Senate in 2006.

Now, Menendez famously finds himself at odds with a president with a very different world view. After all, President Barack Obama grew up in multicultural Hawaii where, unlike Jersey, beaches outnumber RICO investigations. It's a president who came to national office on the anti-war side of his party and expounding the view that dialogue with Iran and Cuba and other enemies would lead to good things, and implicitly suggesting that his work as a bridge-builder in the Illinois state Senate and at the Harvard Law Review made him uniquely qualified to repair the breach between the U.S. and the rest of the post-Bush world.

Those two worldviews are now in clear conflict. As the Obama administration tries to reach a nuclear deal with Iran by next month and as it initiates a dramatic opening to Cuba, it finds itself on the opposite side of Menendez, who is the ranking Democrat on the Senate Foreign Relations Committee. The roads to containing Iran, producing a war resolution against the Islamic State, better known as ISIS, arming Ukraine—each of these goes through the committee where the president would understandably prefer a yes man leading the Democrats but instead gets a fighter. In recent days, The New York Times and other news outlets have shone a spotlight on Menendez, the thorn in Obama's side, which makes sense. The two even had a tiff at a Democratic retreat last month when Obama urged sanctions supporters to put politics aside. Menendez said it was principle. No drinks were thrown, but it wasn't good.

The biggest issue between the two men now is Iran. Menendez backs stronger sanctions—something the Obama administration has vowed to veto, insisting that such measures would scuttle the sensitive negotiations with Tehran. Menendez and Senator Mark Kirk, a Republican, agreed to back off a vote until March to give the negotiations more time. But the talks have dragged on before and it's likely that the showdown between Menendez and the president has only been postponed.

So the opposition between Obama, 53, and Menendez, 61, is real, ideological and serious. But it's more nuanced than the press lets on and more revealing about both the Senate and presidency. "It's not a simple story," says one insider.

To understand the tale you have to know that Menendez and Obama arrived in the Senate at about the same time (2005 for Obama, 2006 for Menendez). But while members who arrive at the same time usually bond, the two were never particularly close. Menendez played an inside game and was more interested in moving up the leadership ranks, while Obama had less interest in lining up leadership posts than he did in planning his 2008 presidential bid. (Interestingly, Menendez's daughter, Alicia, who is a Harvard-educated anchor for Fusion, the English-language Hispanic network, seems more comfortable in public than her father.)

So while Obama cut a national profile, Menendez quietly worked his way up through the Senate Foreign Relations Committee, a powerful body that has been the forum for some of the most contentious fights in American history. It's where Woodrow Wilson's League of Nations was challenged by Republican Henry Cabot Lodge and it's where an Arkansas segregationist Democrat, J. William Fulbright, became an unlikely opponent of the Vietnam War and held hearings in 1966 that became a veritable teach-in against Lyndon Johnson's Southeast Asian quagmire.

For most of his presidency Obama's friend John Kerry ran the committee, and Menendez was little more than a reliable vote for things like health care and the stimulus. But when Obama tapped Kerry to become secretary of state in 2012 to replace Hillary Clinton, Menendez assumed the top role—generally supporting the president, greasing the wheels for various treaties and helping to confirm Obama's foreign policy team, including Kerry himself. But Menendez, a Hillary Clinton backer in '08, was also, in the eyes of the White House, at best difficult and, at worst, antediluvian—a throwback who hadn't gotten the hope-and-change message.

Menendez was an early advocate for arming moderate Syrian rebels, which the Obama administration resisted even as it drew red lines about the use of chemical weapons by the Assad regime. Eventually, Obama came around to Menendez's thinking and the U.S. is now supporting rebels in Syria. By all accounts, there was no moment when the president called Menendez to say, "You were right."

And this is the problem with the Obama presidency that's illuminated by the split with Menendez. Obama has never really had a plan to deal with Democrats who stick it to him whether out of ideological conviction or personal politics, like on coal or gun control. (Let's leave aside the Republicans who Obama was never really able to manipulate, despite those who think that more dinners with Mitch McConnell would have been a balm for the last six years.)

Within the Democratic ranks, Obama does have leverage—fund-raising, endorsements, the powers of the office—but he has never exercised it terribly well. In the case of Menendez, the two men don't speak often on the phone. (When Menendez wants to talk things out he calls Vice President Joe Biden and Kerry, his former Senate colleagues.)

The president's less than interested in massaging or trying to work through policies where they disagree. For instance, in the case of the president's Cuba initiative there was no way Obama was going to see eye-to-eye with Menendez, who is congenitally opposed to letting up on the Castros until they dismantle their regime. But Obama barely gave Menendez a heads up of his Cuba announcement, which seems like an unnecessary slight. And while most of what's been proposed by the White House concerning Cuba is unilateral, there are still opportunities for common ground with Menendez, such as determining which diplomat represents the U.S. in Havana.

The issue isn't Obama's unwillingness to compromise on legislation. He certainly did so on health care reform and other signature bills. But when it comes time to deal with a contentious legislator like Menendez, there's no real plan of action. Bill Clinton would try to flatter his enemies to death, occasionally tempering them as he did the likes of Bob Kerrey. Lyndon Johnson tried to muscle Fulbright, with only limited success.

So far if there's been any handling of Menendez it's backfired. When it comes to Iran, Menendez publicly accused the administration of "fear mongering" and went further when he said the administration's talking points on Iran sanctions sounded like they could have come "straight out of Iran." The White House didn't launch a charm offensive or any offensive to rein him in. And when Menendez has played ball—he has never stuck it to Obama on confirmations and is helping line up an Authorization for Use of Military Force against ISIS—there hasn't been much praise.

Now, with another set of sanctions looming against Iran, the question is whether Obama and Menendez can find a way to work together. So far Menendez has helped stave off some of the more extreme sanctions proposals being pushed by Republicans in the Senate Banking Committee. If multilateral negotiations to tame Iran's nuclear program fail—and that seems more likely than not—can Obama, the smooth Hawaiian, find a way to work with Menendez, the tough Jersey guy, to compromise? Don't bet on it.