This is a perennial question which has flummoxed Republican strategists for years and continues to defy conventional political logic and planning. While it is impossible – and politically perilous – to attempt to take any American demographic group and treat them as a homogenous block, on the major issues of the day one would think that the GOP would be a natural fit for the majority of American Jews. When you look, in particular, at which party provides the staunchest support for Israel, there really is no comparison. A host of other topics appear to be a good fit as well, as Zev Chafets observes in an editorial for Fox News.

The American Jewish community – white, assimilated and prosperous – is out-of-place in a Democratic Party determined to build a coalition around an appeal to racial gender minorities, unmarried women, the LGBT community, immigrants and the dependent poor. And while the Jewish community is shrinking because of low birthrates and intermarriage, its Orthodox wing – strongly pro-Israel and socially conservative – is gaining in numbers and self-confidence…

All this, according to some conservative pundits, has created a tipping point. In November, they say, Jews could turn out in key congressional elections, especially in Senate contests, and vote for Republicans who have made support for Israel a signature issue. And in 2016, fed up with Obama’s chilly attitude toward the Jewish state and his weakness in the face of Islamic aggression, Jews could abandon their traditional affiliation with the Democrats and give their energy, their contributions and their votes to the Republicans.

Sounds good, right? This is a sunny, optimistic view which has trapped more than a few campaign managers across the country. And to be sure there are a number of highly respected Jewish community leaders, bloggers and business people who are very vocal supporters of the GOP and their support of Israel. So does Zev think that this is finally the year when the rank and file will assemble along the same lines?

I hate to rain on anybody’s inaugural parade, but this is sheer fantasy.

Jews are not simply supporters of the Democratic Party; they are at the heart of everything from union leadership to campaign funding, think-tank policymaking to grass roots organizing…

The fact is, the great majority of American Jewish Democrats see their party and its agenda as their secular religion. Reform Judaism, America’s largest Jewish denomination, is sometimes jokingly called “the Democratic Party with holidays.” A lot of Jews would sooner convert to Shia Islam than leave the party of their forefathers.

I wish I had all the answers to these questions and could make a case that Zev is wrong, but I can’t. We struggled with the same things in New York during the 2010 campaign, working vigorously with leaders in the Jewish community, reaching out and looking for a foothold. We lost the Jewish vote in a landslide.

I think some of the assumptions which Zev notes as common knowledge in his piece are also somewhat hollow. For example, I believe that it’s true that the lion’s share of American Jewish voters are strong supporters of Israel. But it’s equally true that these are not single issue voters, and that one policy stance alone is not enough to get them hoisting a new flag. Further, Chafets’ characterization of Jews as white, assimilated and prosperous is not only a generalization, but borders on offensive. There are plenty of folks in the Jewish community who are struggling in a tough economy just like everyone else, and policies which benefit the economically successful don’t automatically become a winning, bread basket issue for them.

Still, it always sounds like the Jewish vote would fit far better with a conservative alliance than with the liberals. Why doesn’t it happen? I wish I could tell you. Is it about to change in 2014? I think Zev is probably on the money here, I’m afraid. I wouldn’t bet the ranch on it.