Hindsight is 20/20, especially for an eventuality that was widely predicted in advance. As such, it’s pretty easy even for pro-Obama partisans to look back and see numerous red flags that should have told them the president’s “Bulworth” moment, in which he’d be fully honest about his feelings toward Israel, was going to precipitate a crisis in U.S.-Israel relations. Nevertheless, there’s always been one red flag that, perhaps unfairly, stuck out in my mind from the 2008 election. And I’m reminded of it again as we read polls showing Obama’s approval rating among the Jewish community dropping during the somber week in which we mark Holocaust Remembrance Day.

Leading up to the 2008 presidential election, both Barack Obama and John McCain sat for (separate) interviews with the Atlantic’s Jeffrey Goldberg, and the subject of their appreciation of Jewish thought and culture came up. Here was the relevant comment from Obama:

BO: I always joke that my intellectual formation was through Jewish scholars and writers, even though I didn’t know it at the time. Whether it was theologians or Philip Roth who helped shape my sensibility, or some of the more popular writers like Leon Uris.

And here’s the exchange from Goldberg’s interview with McCain:

JG: Not a big Philip Roth fan?

JM: No, I’m not. Leon Uris I enjoyed. Victor Frankl, that’s important. I read it before my captivity. It made me feel a lot less sorry for myself, my friend. A fundamental difference between my experience and the Holocaust was that the Vietnamese didn’t want us to die. They viewed us as a very valuable asset at the bargaining table. It was the opposite in the Holocaust, because they wanted to exterminate you. Sometimes when I felt sorry for myself, which was very frequently, I thought, “This is nothing compared to what Victor Frankl experienced.”

There’s nothing wrong with enjoying Roth’s work, of course. But Obama’s answer smacked of check-the-box pop blandness. When it came to discussions of philosophy and literature, Obama always seemed to be reading from Wikipedia summaries. McCain’s answer, on the other hand, demonstrated deep and true engagement with the subject matter, and it showed why his respect and affinity for the Jewish people came through so strongly.

Put simply, when it came to Jewish thought and history, McCain simply got it. Obama was lost at sea.

Which is why Obama’s flagging approval rating among Jews isn’t too surprising, whereas a major change in the presidential vote share would have been more surprising.

It makes sense for American Jews to register disapproval of Obama at this point in his presidency, for a few reasons. First, he’s earned it. Obama has never been able to fake a connection with the Jewish people that just wasn’t there, the way it was with Bill Clinton or George W. Bush. He never passed the “kishkes” test, so to speak, and never even really came close to passing it.

So he was always dependent on his policies speaking for him. Some of the president’s defenders try to point out that Obama has just pushed for a peace agreement along the lines of his predecessors, and that he is unfairly maligned for it. This is false: the differences may appear subtle to outsiders and rookies, but they are monumentally important.

Additionally, he has less of a margin for “error,” as it were, with his policies because he couldn’t make anyone believe that he truly loved the Jewish state and merely wanted what was best for it. Therefore, the trust in him was always going to be less when it came to throwing tantrums over Jewish residents of Jerusalem and the like.

The second reason it makes sense for Jews to make their voices heard now is that Obama has already been reelected, and so there won’t be any concern by left-leaning Jews that they may drive voters to (gasp!) vote Republican, or take other such action that would have actual consequences. This is a safe protest. It lets the president know his juvenile hounding of Israel and his overall incompetence are areas of genuine concern for a demographic group that has consistently been among his most reliable supporters.

And the third reason is that, as far as electoral coalitions are concerned, the Obama era is over. Not only are we past his reelection, but we’re also beyond the second-term congressional midterms. This, then, is a message to Hillary Clinton and the Democratic Party leadership for 2016.

In the end, it probably won’t matter much, especially because Hillary will no doubt say the right things over and over before Election Day 2016. That is, perhaps American Jews still haven’t reached their limit yet. But they can be sure that Obama, through trial and error, would like to discover precisely what that limit is.