To pray at the KAM Isaiah Israel synagogue, a striking tan brick building of Byzantine inspiration, one must first contend with the cops. They are stationed at either end of the two streets that abut the domed building, and they require a photo ID and a purpose to pass the metal barricades and cement dividers. In certain cities, the officers would be there to guard such a conspicuous site of Jewish worship from its gentile neighbors. In the Chicago neighborhood of Hyde Park, it is just the opposite.For across the street, behind its own layer of police protection, another brick building stands. This one is deep crimson, with a white colonnaded porch and pink impatiens along the walk. Its more conventional style belies most atypical residents: what might be the next first family of the United States.The journey that has taken Barack Obama from Chicago to Washington, one that might lead from a red brick house to the White House, began in this integrated, eclectic neighborhood where he was close to Jews physically, professionally and politically.Along this journey, Obama has encountered other Jews, people who don't know him personally and who repeatedly ask: Who is this guy? The Jews of Chicago say: We have the answer. Many who have employed him and fund-raised for him and voted for him are now trying to reassure those wary Jewish voters.In doing so, they tell of someone who has at times been more welcome in progressive Jewish circles than in the black community, circles where he built lasting friendships and a political foundation that have helped propel him onto the national stage. Along the way, many of the liberal positions they once praised him for - or projected onto him - have been discarded, those on Israel included. That has left some dissatisfied and several dubious, but many excited at the thought that they might have to help their neighbor pack his bags come November 5.TO TRACE the story of Obama's Chicago Jewish political connections, one needs to start in Boston.The story, as long-time acquaintance and major Jewish philanthropist Lester Crown tells it, goes something like this: After graduating from Columbia University and working in Chicago as a community organizer in his early 20s, Obama left this Midwest metropolis to attend Harvard Law School. One day back in Chicago, Crown's good friend Newton Minow received a phone call from his daughter Martha, a Harvard law professor, telling him, "You ought to interview the smartest young man I've ever had in any of my classes." According to lore, when Minow called a partner in his firm to recommend he meet with Obama during a visit to Harvard, the partner told him he had already been hired for a summer internship.Obama's experience at the Sidley Austin firm, where he soon got to know Minow, a former Federal Communications Commission chairman (as well as his future wife, Michelle Robinson), was crucial in introducing Obama to leading local Jewish figures like the billionaire Crown. Crown first became acquainted with the young associate after Minow suggested he meet this "special" guy who "is going places." And indeed, Crown describes him as "brilliant" and "a quick study," though he does not pretend to have pictured Obama sitting in the Oval Office during their early encounters.These kinds of introductions proved key for Obama's construction of a network which would eventually support his political aspirations. The Crown family, for instance, have been major financial backers, with Lester's son James serving as Obama's Illinois finance chairman."He's developed very close relations with the Jewish community in Chicago. If you look at fund-raising, etc., the people who primarily support him are Jewish," says Crown. For starters, above his son in the fund-raising structure is Penny Pritzker, another local Jewish billionaire and the national campaign finance chairwoman. And along with Martha and Newton Minow, another of his earliest and most important mentors was former Chicago congressman and federal judge Abner Mikva, who ended up providing key political backing.Obama turned down both Mikva's offer of a clerkship and Minow's offer of a slot at Sidley Austin, however, to take a full-time job with a different kind of Jew and a different kind of lawyer.Traveling from the soaring skyscraper of Crown's General Dynamics office, with its panoramic city views, heavy furniture and carpeted hallways, to Judson Miner's perch in a cozy historic town house, complete with exposed brick walls and a cluttered fireplace mantel displaying a picture of himself with Obama, is to cross a different world. As opposed to political heavyweights and establishment types, Miner is scruffy, progressive, a religious skeptic.Miner, in fact, made a bid to recruit Obama when he read in the Chicago media that the first African American president of the Harvard Law Review wanted to work in civil rights but was bound for what Miner termed the "silk stocking firm" of Sidley Austin. In turned out that was inaccurate, as was the press report that he had worked his way out of the Chicago ghetto to get to Harvard. (In fact, Obama was born in Hawaii and raised by his white mother and her family after his Kenyan father returned to Africa. He didn't come to Chicago until after college, and his lack of black bona fides would be a major obstacle when he later ran for the Illinois senate.)Miner was a leading Chicago civil rights lawyer, one whom it turned out Obama had heard of because of the time Miner had spent as the corporation counsel for the city. Miner didn't know that when he called the Harvard Law Review trying to recruit the star student. He was told to take a number - in the high hundreds.But to Miner's surprise, Obama tracked him down at home and after a series of conversations ended up taking a job at Miner's firm. He recalls Obama as "strikingly comfortable with who he was," someone who didn't feel the need to trumpet accomplishments such as heading the law review. "What was particularly impressive about Barack was that for a person with his credentials, he was happy to be an associate and do basic research and not take the lead." He stayed at the firm even after he won his state senate seat in 1996, though it greatly limited his hours there.His work for Miner, a well-respected name in civil rights circles, connected him to more Jewish progressives, who also corresponded to those he met in his neighborhood. "There was a natural contact - not because they were sought out," Miner explains. "A lot of them live in Hyde Park. A lot of them are involved in progressive legal activity. So they were the people he'd meet."TO CATER to an expanding population, KAM Isaiah Israel opened the doors of its Hyde Park synagogue in 1924, as the neighborhood was soon to experience its Jewish population peak of upwards of 20,000. Many of the congregants were attracted there for the same reasons - a green, lakefront district close to downtown - that the neighborhood had originally been established as a summer retreat for the wealthy in the mid-1800s. Once public transportation cut the travel time and cost to the city - today a mere 15 minutes - middle-class Jewish merchants swarmed in. Many Jews were also pulled to the neighborhood by the prestigious University of Chicago, which opened shop along with the train in 1892 and created an intellectual, liberal enclave. To this day, many people who come to study end up staying. And many professors, such as Obama, make their homes nearby.The tenor of the neighborhood changed following World War II, as it did in many major American cities, when suburban expansion and new wealth drew middle-class residents - Jews included - to the suburbs as the poorer black population further south moved in. With sinking property values and increasing crime, by 1960 the University of Chicago weighed relocation. Other communities' Jewish residents were pouring out, though many often retained the leases of the property they left behind."That was the death knell of any kind of Jewish-black relations because the Jews were seen as the landlords and the owners of small businesses," remarks Emily Soloff, who has worked with the black community in her capacity at the American Jewish Committee's Chicago office. "Hyde Park is the exception to this because Hyde Park is a more integrated community, in part because the University of Chicago has really held the line, because the University of Chicago decided to stay, buy more land and provide security."The move helped anchor the white progressive community to the neighborhood alongside the black middle and upper-middle class. And, according to Chuck Bernstein of the Chicago Jewish Historical Society, two liberal rabbis at the time also urged their members to stay put."They made a very strong stand against white flight, which was not the same in many other communities," he noted. As a result, he said, "It's an integrated community - one of the few successfully integrated communities in America." And that in turn bred a more liberal population.KAM Isaiah Israel rabbi Arnold Jacob Wolf first came to Hyde Park to attend university in 1940 and returned for good in 1980. The white-bearded and avuncular Wolf recently retired but still has an office at the synagogue, filled with holy texts and family photos.He describes the Jews who chose to stay in the neighborhood as "very proudly Jewish, but in a universalist mode - interfaith, left, liberal, integrationist. The others moved away, to the suburbs." Proudly Jewish - and proudly political.Many, including Wolf himself, would fund-raise and canvas for Obama. In fact, the first time Wolf saw him was at an informal fund-raiser he had agreed to hold for the rising star then running for state senate. He thinks it was held in his own home - at 84, he quips, "nothing is definite" - but is sure of what he told him when they met. "I said to him, 'Mr. Obama, someday you will be vice president of the United States.' And he said, 'Why vice president?' and laughed."Though Wolf didn't say "president" because he couldn't imagine a black man winning the White House in his lifetime, others who had the same strong reaction could."I immediately thought, he's going to be president some day," longtime liberal activist Bettylu Saltzman said of her first meeting with him, as quoted in the Chicago Jewish News.Saltzman played a particularly key part in Obama's career, as she was the one who asked him to speak at the peace rally she organized in 2003 where the then state senator gave his famous speech opposing the Iraq war - a position at the core of his argument for the presidency.Reached at her home, Saltzman said she would only speak to The Jerusalem Post with permission from the Obama campaign, which refused to grant approval, though it granted other interview requests.TO WORK with Jews, though, requires involvement with Israel. Eventually, it became important that Obama take up the subject. He was prodded on that front by Jack Levin, another key Jewish backer who first met Obama in his law school days. A Harvard Law School alumnus himself, Levin was part of a group visiting the school when someone pointed out Obama as being exceptional, about the only time Levin remembers a student being brought to his attention that way. He became better acquainted with him when they were both teaching at the University of Chicago law school, another rare feat for a recently minted lawyer, particularly in the prestigious field of constitutional law.Levin, an intellectual property lawyer whose office shelves of crystal plaques testify to the multimillion-dollar deals he's helped broker, offered to hold a fund-raiser for Obama early on in his run for the US Senate in 2003 but told Obama that he would need a position paper from him on Israel.He recalls that Obama was reluctant, telling him, "I don't want to put out any position papers yet because it just makes it easier for people to attack me." But the executive board member of the American Israel Public Affairs Committee's Illinois chapter informed Obama that 70 percent of the turnout would be Jewish and that without a paper detailing his positions on Israel, he would inevitably spend the whole event fielding questions on the topic."Perfect" is the word Levin uses to describe what Obama eventually wrote. "I didn't have to suggest that he change a word. It was A-OK." Levin summarized the paper's contents as hitting all the bases: stressing the right of Israel to defend itself, defending the legitimacy of the security barrier, condemning Hamas and recognizing the need for a fair and just peace.When it became time to enter office, community leaders became more active in suggesting he visit Israel personally, which he did once in the US Senate.Close family friend and fellow Chicagoan Cindy Moelis remembers that trip well, having talked to Obama before and after he want."It was really because the people who supported him in Chicago made it clear that this was one of the most important issues, and one that he had to get educated on," she says of the impetus for the visit. Afterward, she relates, "He came back in awe. He was blown away."Noting that his visit was at that time more recent than her own last trip - which had been when she was a teenager - she says that his description of the places he had seen and the people he had met "reminded me how beautiful the country is.""He was touched. He got an appreciation of the people in Israel. He got an appreciation of the security needs," says Lee Rosenberg, who accompanied him. A long-time AIPAC board member, Rosenberg had many conversations with Obama on the Middle East and Israel as Obama's US Senate campaign heated up. Rosenberg, sitting by his office bookshelf on which a Haggada and Alan Dershowitz's The Case for Israel keep company, recalls "a great alignment of thought" between them.Rosenberg introduced Obama when he delivered his speech before AIPAC in Washington the day after tying up the nomination. That speech was well-received by much of the pro-Israel community, parts of which have expressed concern over Obama's Middle East policies and questioned where he stands on Israel.His hawkish remarks - including his justification of Israel's preemptive strike on an alleged Syrian nuclear site and his stress that military action against Iran remains on the table despite his willingness to talk to Teheran's leaders - allayed some of those concerns. But he also turned off some people when he declared that Jerusalem "must remain undivided" only to have his campaign clarify the next day that he was not ruling out shared sovereignty with the Palestinians."He's good on Israel and he has relationships with the Jewish community, and I don't know how many times you have to say it," says an exasperated Crown, who sent out an open letter to the Jewish community making the same point during the primary campaign.Crown acknowledges that Obama has a different perspective on Israel. "He obviously doesn't look at it in the same historical context as I do. I'm sure the subject hasn't been anywhere near as important to him, so he doesn't have the depth of knowledge."And he adds that perspective leads Obama to have "empathy with the Palestinians, no question about that" which goes beyond his own."He looks at the situation much more today than in the historical context of how it occurred, so I think he certainly has more empathy than I would, but that doesn't in any way dilute his feeling that the survival of Israel is essential, and it's essential as an ally of the United States."TO HENRY GENDLER, Crown's description of Obama's sympathy for the Palestinians rings true, but not much else when it comes to assessing the Democratic presidential nominee's stance toward Israel.Gendler, a German-Jewish immigrant, lived next door to Obama in Hyde Park for 10 years before he moved across the street from KAM Isaiah Israel. A member of the Republican Jewish Coalition, he frequently chatted about politics with Obama when they ran into each other outside.Neighbors rather than friends, Gendler suspects that if Obama were told his name, he wouldn't have "a clue" who he was, but "if you tell him about the chubby guy with the German accent who was his neighbor in East View Park, that could trigger his memory, because my accent is pretty strong."Normally, Gendler recalls, Obama would be happy to stand in front of the building and talk but "when it came to Israel, it was not like that." Instead, he says, "when Israel started to become the topic, he became very cold. He always told me that we need a more 'balanced' approach, which in America is a code word for being too pro-Israel."Yet he can point to no specific policy points or comments that Obama made to flesh out that attitude. "He would refuse to talk more about it, [but] he gave me the impression that we were far too pro-Israel."Like other detractors, Gendler notes how affable and personable Obama was. "He was always positive. He never lost his temper. On a personal level, he was very nice."Fellow Republican Ron Gidwitz also praises Obama for being "friendly" and "warm," but remarks, "I've probably known him longer than most of these people have, though maybe not as well... but I elected to support John McCain." Gidwitz and Obama once served on a school reform board together and as Gidwitz remembers it, "Barack showed up at meetings but was not terribly active."Both men also think the adulation they hear heaped on Obama is overdone. "I want to laugh because they make him look like a half-god," Gendler says. "He's a regular guy. He's smart but he's not smarter than I am. He went to Harvard for grad school, but big deal. I went to the University of Chicago."But what rankles Gendler most is the what he sees as Obama's brand-new attitude toward Israel. "Now it's like he wants to hug and kiss Israel every five minutes. That's completely not the Barack I had as a neighbor. That started this year, when he was trying to get elected."Wolf, the KAM Isaiah Israel rabbi emeritus, also detects a shift in Obama's political posture that leaves him distressed, but for the opposite reason. "In general he's much more cautious than I thought he would be about everything," Wolf says.At first, he acknowledges, he never expected Obama to even win so much as the presidential primaries. "The people I support don't usually win. I'm used to losers," he says. "I'm far too left to win - and then of course it turned out he wasn't as far left as I was."Like Gendler, Wolf has impressions about Obama's initial views on Israel more than specifics, and the impression was one of sympathy for the views that he and their mutual friend, Palestinian advocate Rashid Khalidi, expressed to him on Israel - views including the need to pressure Israel to give up the West Bank.In retrospect, he believes that Obama was carefully considering their perspective rather than endorsing it. "When he was listening, we had his ear, but he didn't come down on our side," he reflects. "I think he was listening and learning and thinking. I don't think that he switched. I don't think he agreed with us."He describes Khalidi as "very disappointed," while saying of himself, "I'm a little disappointed, but I'm also relieved." He explains that despite the letdown, "I'm glad he's not as doctrinaire as I was because then he can pick up some independents and he can win."As an example, he points to Obama's AIPAC speech."He came to AIPAC and said exactly what they wanted. He wasn't insincere. He was centrist. A lot of his supporters are Peace Now people, but he's not," he says. "You can't go to AIPAC and insult them. You have to give them something they'll listen to. I can't do that, but he did that, and he was right - and also disappointing."While he might lament this "move to the center," as he puts, he also understands it: "It seems to work."Like Wolf, Miner is excited about winning, and is therefore willing to see some issues compromised."Barack is about being successful, and being successful is about making sure that a majority of people support what you want to do, and sometimes that means massaging positions," he says. "I've never known Barack to abandon principle, but as a lawyer Barack was always looking for a way to present an argument that wasn't offensive to the other side but made his points. Barack is not an ideologue by any stretch of the imagination. Barack likes to work things out. That's what he does."Joel Sprayregen also doesn't fit the definition of an ideologue. Another Chicago lawyer and self-described "liberal who has been mugged by reality," i.e. a neoconservative, he has voted Democrat in six of the last nine elections, most recently for Al Gore in 2000, and would have considered backing Hillary Clinton had she won the primaries.Sprayregen, however, doesn't believe that Obama is a moderate. Associations with people like Khalidi make him doubt Miner's words."The overwhelming majority of his formative contacts in the political context were extreme leftists," Sprayregen charges. "Until I'm convinced otherwise, I think his heart of hearts is on the extreme left.""What I am intellectually comforted by is that so many fine, bright, committed Jews support him, Lester Crown and Alan Solow among them," he acknowledges. "They're pro-Israel Democratic people, and they're people that I respect and admire, which obviously on the one hand inspires me to reassess my thoughts, but on the other doesn't convince me I'm wrong."Solow, a litigator and JCCA of North America chairman, says he finds reassurance precisely in the fact that Obama and Khalidi were friendly. "The fact that Khalidi knew him wouldn't have caused a ripple for me because everybody knows everybody in Hyde Park... I feel good that Barack Obama had friends in the Palestinian community and notwithstanding that has taken strong positions in favor of Israel."But unlike Obama's relationship with Khalidi or '60s radical William Ayres - who can be considered a mere colleague and passing acquaintance - the one most troubling for Sprayregen is one that was deep, significant and lasted until this spring: that with the Rev. Jeremiah Wright.TO REACH the Trinity United Church of Christ, it is necessary to drive 15 minutes south of Hyde Park - through stretches of rundown buildings and abandoned lots, through working-class barrios and streets where white faces are few and far between - or to circumvent it all via the freeway. But once there, one finds a middle-class neighborhood of boxy, white, one-family homes divided by neat lawns. It is in this place that Obama connected with religion, as well as his black identity and fellow citizens, while working in the South Side as a community organizer.And it is where he met Wright, his spiritual mentor who would officiate at his wedding, baptize his daughters and supply the title for his second book and presidential theme: the audacity of hope.It is also where Wright made incendiary comments which horrified wide swaths of the white and Jewish community when they were reported during the presidential campaign, including shouting "God damn America" during one sermon and calling Israel's actions "state terrorism" during another, which Obama has said he didn't attend or hear about until recently. Wright also praised Nation of Islam leader Louis Farrakhan, despite his anti-Jewish statements, and reprinted an op-ed by Hamas in church publications.These episodes seem an insurmountable, and unexplainable, obstacle to critics like Sprayregen - though if Obama's relationship with Wright was the deepest of his problematic associations, it is also the one he most publicly and irrevocably broke off.Many of Obama's Jewish supporters say that while they were disgusted by Wright's behavior, they weren't troubled by his connection to Obama because they know he doesn't think that way.Solow, for instance: "The hateful things that were shown on TV over and over [are] diametrically opposed to not only what Barack Obama believes and has said but also the way he's lived his life."Moelis echoes his comments, adding that she hadn't heard anything about Wright's incendiary comments until after the national media reported them. The only time she saw him in person was at the Obamas' wedding when, she says, "he talked about love and commitment and marriage."Jewish groups that have visited Trinity have also received a different impression of the pastor and his church. The American Jewish Committee's Soloff recounts bringing a group of German Christians who were visiting the city. Wright spent an hour meeting with them ahead of the service, speaking to them in German - one of the many languages he speaks - greeting them again from the pulpit and having the choir sing a song of welcome for them in German."It was tremendous hospitality," says Soloff, who adds Wright was fully aware she was from the AJC and made no issue of it.Wright has since retired, but the current congregation is still very welcoming. Indeed, 30 minutes into a recent Sunday service - the time when people had finished filtering in and chatting and things were really getting started - Wright's young and dynamic successor, Otis Moss III, instructed all the members of audience to introduce themselves to one another. Politics was limited to a letter passed out to the several hundred congregants in attendance advocating debt relief and other fiscal measures, addressed to politicians including Obama. His only reference to Jews was by remarking on their special relationship to God at the end of a sermon using Jacob and Esau's rivalry as a lesson on dealing with family dysfunction."You cannot possibly get a sense of what Trinity Church says or does or believes based on what you see in the media, because it was all cherry-picked," maintains Soloff. "The church got so abused by the media."When it comes to Israel, Soloff argues that its positions are no different than many other mainstream non-evangelical churches that have a reputation for being sympathetic to the Palestinians and in some cases starting divest-from-Israel drives, a phenomenon the AJC has actively worked to counter. She points out that it's unusual for a black church to be affiliated with the United Church of Christ, one of the more liberal denominations."I didn't have a sense that Wright was beating a drum for the Palestinians, but that the mind-set of the church was to lift up the situation of the Palestinians in the same way that you would see in any other Protestant church where the underlying belief is that the Palestinians are the underdog and that the story of the Palestinians isn't told in the US media," she says.She points to a racial dimension as well, as much of the black population identifies with the Palestinians and is therefore reflexively sympathetic to them. And she adds that Jews and blacks for the most part live separate lives in Chicago - Hyde Park being an exception - so there are few chances for dialogue.What interaction there has been hasn't always been positive, either. Some of these tensions are ones Obama faced as he tried to cultivate support in a black community that often saw him as an elite carpetbagger. His decision to join Trinity was criticized in some quarters, for instance, as being politically motivated for the connections he would make."He's not looked at by the black community here as being a real insider because he didn't grow up here and hasn't been a part of it all of his life," Crown says. "As he didn't have to [work to] develop a tie to the Jewish community, he did have to work on developing a tie to the black community, especially when he wanted to run for state senate here."Wolf describes him as different from other black politicians - less gregarious, more respectful - as does Miner, who calls his situation a "very difficult tightrope" where he had to appeal to the black community without losing his toehold among the Jews, who were an important source of political support in part because they serve as an entry point to the wider white community.But Miner notes that he got a political payoff from that, too, as he became a black politician who many Jews felt was more similar and approachable than other such figures."He was very comfortable with the white progressive community," Miner says. Other black pols "didn't speak as fluently as Barack did." In fact, Miner and his wife would joke with Obama that he's actually an Ethiopian Jew.And more than one Jewish backer has pointed out that he represents in some ways the classic Jewish American story: A wandering, rootless person moves to the big city, goes to good schools, works hard and becomes a lawyer."I think Jews identify with Obama more than you would expect," Wolf says. "We work for liberal politicians all the time, but it's more or less routine. This is not routine at all."Miner says that despite the claims in the Jewish community about the ways in which that work has been done on Obama's behalf, and the extent to which those people in Hyde Park and elsewhere are trumpeting it today, he attributes the success to the man himself."I'm a great believer that Barack didn't need a lot of people to open doors for him, he opened them himself - though people like to take credit for opening doors for him."