There have been a spate of articles recently about Obama and the Jewish vote, the most recent by Bret Stephens in the Wall Street Journal. Without exception, these articles have focused on whether Obama is or is perceived to be sufficiently pro-Israel to retain Jewish voters.
The answer is, "yes," as these articles consistently conclude. But I think the authors are missing the broader picture, which I've tried to emphasize. In short, Israel is not going to be a major issue in this campaign, but the comfort level of Jewish voters with the candidates will be.
The Republican presidential candidates since 1992 have been especially unattractive to Jewish voters, and the Democratic candidates especially attractive. The elder Bush did relatively well (about 35%) among Jewish voters in 1988, basking in Reagan's reflected glory. But by 1992, Jewish voters saw him as an out-of-touch WASP patrician (the kind of guy who kept your dad out of his country club) who had top advisers who said things like "Fuck the Jews!" (that was James Baker). Meanwhile, Bill Clinton, with a host of Jewish friends and acquaintances, was the most conservative Democratic presidential candidate since at least JFK, giving habitual Jewish Democrats little reason to vote for his opponent.
Bob Dole, who had no particular "Jewish" connections, was no match for Clinton, who, not incidentally, had far more Jews in high-level positions in his administration than any president in history, including both of his Supreme Court nominees. Bush II had the disadvantage of being his father's son, and a devout conservative evangelical Christian, running against Al Gore. Gore's daughter married a Jewish guy, and went all over the country campaigning for him among Jewish voters, not to mention that Gore was able to bask in Clinton's glory, and of course choosing a moderate Jewish running mate. Bush II did a bit better in 2004 (24%) after he proved to be quite friendly to the Jewish community and Israel, and while running against a more liberal opponent. But he was still no match for Kerry, with his Jewish grandparents, Jewish brother (converted), and strong ties to the Northeastern liberal community of which Jews are an integral part.
Fast forward to 2008. Obama is probably the most liberal candidate the Democrats have fielded since at least Walter Mondale, perhaps since George McGovern. Contrary to popular belief, very liberal presidential candidates make a substantial percentage of Jewish voters nervous, especially with regard to national security issues. If you were going to have a longtime minister/friend/mentor who makes Jews nervous, Rev. Jeremiah Wright, with his inflammatory rhetoric and ties to Louis Farrakhan, is straight out of central casting. Obama's ties to radical leftists such as Bill Ayers are also of concern, given that the radical left's hostility to Israel, objectionable in and of itself, blurs into anti-Semitism all too often. And Obama's relative novelty leaves at least some voters wondering whether they know enough about him and his unique background to trust him.
Meanwhile, consider the relative advantages McCain has over recent Republican presidential candidates: He has Joe Lieberman, exactly the person to win over moderate Jewish voters, backing him fiercely; an open, outspoken, judeophilic brother; tenuous and often difficult ties to the Christian right; a relatively moderate image; and a strong record on Israel.
In short, the 50% of Jews who would vote for just about any Democrat aren't going to swayed. Neither are the 15% or so of Jews who supported the Bushes in 1992 and 2000. Of the remaining 35%, who are mostly moderate politically, the question is as much about comfort level as about policy. Consider that Reagan did extremely well for a Republican among Jewish voters, even though he was the most conservative Republican candidate since the New Deal save Goldwater. But this Hollywood actor with a long history of writing for Jewish newspapers and with many Jewish friends appealed to many Jews in a way that his more moderate successor, George H.W. Bush, could not. The relevant implicit question is, "in whose social circle would I feel more comfortable?" In recent elections, it's been rather clear where most Jews thought they would "fit" better. With regard to McCain versus Obama, I think the question is very much up in the air.