Diplomatic relations, like human relations, involve both symbols and substance. One of the disturbing phenomena we are witnessing in President Barack Obama’s White House is that, when it comes to Israel, Obama is fumbling on the symbolic level while pressuring Israel substantively.

That’s why the White House decision to award Mary Robinson the Presidential Medal of Freedom is so disturbing. It sends a symbolic message of disrespect to Israel – and to Jewish sensibilities – at a time when relations with Israel are already tense.

Granting Mary Robinson America’s highest civilian honour is a surprisingly unnecessary, self-inflicted wound. A former president of Ireland and former United Nations High Commissioner of Human Rights, Robinson’s reputation is forever stained by her failures of leadership during the Durban debacle of 2001, when a UN conference against racism degenerated into an anti-Semitic hate-fest. She also has been very critical of Israel, and at crucial moments during her UN tenure from 1997 to 2002, she failed to pressure the Palestinians to swear off terrorism. It would have taken about 10 seconds of Googling to discover that Robinson is controversial.

As of this writing, no one has come forward to admit nominating Robinson, and the White House spokesperson made some mealy-mouthed comment about not agreeing with everything she’s ever said. Dr. Tevi Troy – yes, he is my brother – the former U.S. deputy secretary of health and human services and a former White House aide, reports that a White House source claimed that the Obama people were unaware of the controversy, which suggests rank, amateurish incompetence rather than gross insensitivity.

This unfortunate choice nevertheless highlights that there are powerful forces within the Obama White House and State Department who see Robinson and swoon – rather than remember Durban and feel queasy. This symbolic slap to the Jewish community, coming on the heels of Obama’s Cairo speech, which suggested that the founding of Israel stemmed from the Holocaust, makes his picking fights with Israel seem mean-spirited.

It’s important not to overreact. Obama has spoken eloquently before about the Jews’ right to a homeland, about the power of returning to one’s roots, and about the need for Palestinians and the Arab world to accept Israel’s existence. But Obama has bought into the Peace Now miscalculation that Israeli leaders need to be bullied to compromise rather than calmed and coaxed. So far, many American Jews have seemed reluctant to criticize the president, dazzled by Obama’s eloquence, committed to his liberal agenda, silenced by his pro-choice leanings and bamboozled by his clever strategy, which manipulatively balanced off Jewish fears about his Cairo speech with a trip to Buchenwald. This trade-off showed an understanding of American Jews’ unhealthy obsession with the Holocaust and growing distance from Israel’s needs.

With a pro-Israel prime minister, Stephen Harper, at the helm today, many Canadian Jews may be tempted to judge American Jewish silence arrogantly. But during the bad old days of former prime minister Jean Chrétien, Canadian Jews were the Jews of silence. During the difficult years of Palestinian Authority president Yasser Arafat’s wave of terror against Israel and the Jewish people, many Canadian Jews were too loyal to the Liberal Party, and too fearful of Chrétien’s wrath, to criticize.

Moreover, in 2004, when I criticized McGill University for giving Robinson an honorary doctorate, most of the organized Jewish community was silent. One leader told me, “I’m sorry you said anything. You’re a nice guy, and I don’t want to see you get bashed publicly.” I told him then that I had nothing to apologize for, that it was Robinson who needed to apologize for her failures to stop the worst outbreak of official anti-Semitism in decades.

On both sides of the border, Canadian and American Jews must remember that we’re free to criticize our leaders and free to praise them, and that we’re most effective by avoiding overly simplistic demonization or deification. Democracies are dynamic, and governance is complex. As citizens in a democracy, it’s our right and our privilege to speak truth to power, asking our leaders to do the right thing, both symbolically and substantively.