It seems prophetic that America’s first foray into the Middle East involved a bribe, and ended, ignominiously, in failure.

Seeking to rescue Americans taken hostage by Barbary pirates, John Lamb, a Connecticut businessman who had once traded mules in the Mediterranean but had no diplomatic experience, arrived in Algiers in 1785 with authorization from Congress to bribe the reigning potentate, Hassan Dey. But instead of releasing the hostages, the dey demanded additional ransom that included a portrait of George Washington, whom he professed to admire.

The fiasco did not stop the United States from paying bribes to secure treaties with other Barbary states, writes Michael Oren, in his compelling new book on America’s involvement in the Middle East, “Power, Faith, and Fantasy” (Norton, 604 pages, $35).

But such ignominious episodes prompted Thomas Jefferson, who had helped negotiate a $20,000 “gift” to the king of Morocco, to argue that his fellow Americans preferred “confrontation with Barbary to blackmail.” Ultimately, Mr. Oren observes, Jefferson used the humiliation of continuing Barbary seizures of American cargo and citizens to persuade a reluctant Congress to finance the nation’s first Navy.

America’s pragmatic use of diplomacy and force to achieve its objectives in the Middle East would become a hallmark of its approach to the region. The Middle East, Mr. Oren argues persuasively, was seminal in shaping American identity — from the drafting of a constitution that, unlike the ineffectual Articles of Confederation, enabled the fledging state to defend its own borders and economic interests overseas, to the lyrics of “The Star Spangled Banner.”

America, in turn, also helped shape Middle Eastern identity and aspirations. The now common term for the region once known as the Orient, or the Near East, Mr. Oren notes in one of his many asides, was coined by an American admiral in 1902.

The Middle East was a series of “firsts” for America: the authorization of its first police action Jefferson’s order to his new Navy in 1801 to sink, burn, and destroy any pirate ship that threatened American vessels — and that same year, the first time America found itself the target of a formally declared war — by the pasha in Tripoli.

From the outset, Mr. Oren writes, the relationship was fraught with tension leavened by cultural curiosity and fantasies about the exotic Orient and more critically, by economic and religious opportunity. Americans always considered themselves morally superior to the Arabs, a conception that “landed with the Pilgrims at Plymouth,” he asserts.

American myths about Islam and the Muslims who practiced it, the “ultimate other,” he calls them, were as deep-seated as they were occasionally inconsistent. The image of the “liberty-loving nomad,” riding alone in the desert, “unencumbered by governments or borders”— a Middle Eastern version of the colonial pioneers, and later the cowboy — clashed with Americans’ perception of the region as backward, brutal, corrupt, obsessed with hierarchy, and often savage enforcement of tribal customs. While Americans fantasized about twisting alleys, exotic bazaars, erotic belly dancers, and lustful Bedouin sheiks at world fairs, in books and newspapers, and later in film, many early American visitors to the region — even Southern slaveowners— could not help but deplore the treatment of Muslim women, an enduring challenge for the region. Before the Civil War, American missionaries and other abolitionists — Horace Mann, Charles Wells Brown, and Theodore Parker, among them — cited the barbarity of Middle Eastern slavery in demanding that American blacks be freed.

Mr. Oren’s sweeping, highly textured history of the 230-year interaction between America and the Middle East told me much I did not know. I was unaware of the fact, for instance, that George Bush, a biblical scholar and professor of Hebrew at New York University — and a forebear of the two presidents — wrote an influential treatise in 1844 on the need for Jews to recreate their ancient state in Palestine. Nor did I know that one of President Lincoln’s assassins was caught after escaping to Egypt, or that the Statue of Liberty’s creator initially conceived of his work as an Egyptian peasant woman who would hold the torch of liberty at the entrance of the Suez Canal. How many Americans know that veterans of both sides of the American Civil War wound up advising military campaigns for the Egyptian khedive in Sudan and what was then Abyssinia? Or that early diplomatic envoys to the region, unlike those sent after the 1920s when the State Department developed its professional corps of Arabists, tended to be Jews?

Mr. Oren’s work is prodigious, drawing upon hundreds of original and archival sources — letters, memoirs, books and government documents, which he skillfully weaves into a finely drawn narrative that alternates among cultural, political, and economic interactions.

One of the book’s major contributions is Mr. Oren’s meticulous scholarship on the influence of American missionaries in the Middle East and the extraordinary impact they had not only on the region, but in Washington.

Missionaries — exemplars of “the American spirit at its best,” as Henry Morgenthau, an adviser to President Wilson and ambassador to Turkey, praised them — printed Bibles in Arabic, opened hundreds of medical clinics, schools, and what ultimately became three of the region’s most prestigious universities. Preaching not only Christian precepts but what Morgenthau called the “gospel of Americanism,” missionaries founded many of the institutions that helped give birth to Arab nationalism.

The impact that other powers had achieved through war and plunder, Mr. Oren argues, Americans secured largely through philanthropy and religiously inspired educational missions. Such work had at least one crucial economic payoff for America: Mr. Oren notes that Saudi Arabia’s King ibn Saud offered oil exploration rights to American, rather than British prospectors partly because he was impressed by the missionary doctors’ reputation for honesty and good works.

But the missionaries failed in their main objective: spiritual salvation. Henry Jessup, the “doyen of American evangelists,” lamented that despite the creation of more than 100 churches and the presence of over 200 missionaries throughout the Ottoman Empire, the number of converts from Islam remained “negligible.”

As later generations of Americans would eventually discover, Islam’s hold over the Arabs, Turks, and Persians repeatedly frustrated the missionaries, partly because of their intense disdain for the religion. Mr. Oren convincingly shows that antipathy toward Islam was both profound and widespread in early America — echoes of which are apparent today. Sarah Haight, a Long Island woman who toured the Middle East in the 1830s, was typical in deploring the “Mohammedanism” that “pulls down … every country in which it predominates.” Walter Colton, a liberal editor and naval chaplain, concluded in 1836 that “Islamism” was “the grave of inspired truth and liberty.”

The flip side of the early missionaries’ hostility toward Islam was their enthusiastic embrace of the restoration of the Jews in the Holy Land. Far more than early American Jews, who were fearful of being labeled un-American, Christian missionaries embraced the goal of returning Jews to Zion.

But Mr. Oren, an American-born Israeli scholar, is honest about what motivated some of them. Like their modern evangelical counterparts whose reverberations are heard in the words of the memorable figures he describes in this often riveting book, “love for the Jewish people” was often not an end in itself, but rather, a “means for hastening Christ’s return.”

Perhaps because Mr. Oren is an Israeli, and therefore keenly aware that his every line is likely to be scrutinized by Muslims and Jews alike for pro-Israeli sympathies or anti-Arab and anti-Muslim bias, he strives to be detached from the historic hatreds and resentments that have long roiled the region, not to mention American departments of Middle Eastern studies.

Only occasionally do strong feelings arise. For example, in his description of the Armenian “holocaust” at the hands of the Turks. His recounting of the slaughter is harrowing, but he barely mentions the larger historical context — such as Russia’s repeated invasions of Turkey in the name of liberating Armenian and other Ottoman Christians. While such factors can never justify massacres, they help explain why they occurred.

For the most part, Mr. Oren remains neutral in his discussion of the Jewish and Arab claims to Palestine and other bitter disputes. At times, the reader yearns for slightly more passion and/or outrage — and a tad more skepticism — from this careful scholar. While America, unlike its European counterparts, never sought to colonize the region, Mr. Oren seems to accept naïvely the alleged purity of American motives and actions in the region.

Nor is it always clear what Mr. Oren means in his references to the importance of “faith” in shaping political views about the region. Yes, President Eisenhower used the word 14 times in his first inaugural address, but as even Mr. Oren acknowledges, in the most secular way. “For the new president,” he writes, faith meant “confidence in America’s ability to protect freedom worldwide” while “respecting the ‘special heritage of each nation.'”

Only in his discussion of the rise of Islamism in the last 50 pages of the book and in his epilogue does Mr. Oren openly disclose his personal conclusions about America’s protracted engagement in the Middle East. Yes, he writes, successive administrations have backed oppressive regimes that advanced American interests and conspired to overthrow popular leaders. And American oil companies have pumped billions of barrels of Arabian oil “not for the betterment of the indigenous population but for their own enrichment.”

Yet for all of its shortcomings, he concludes, America has been “unrivaled in introducing modern education and health care to the region, in extending emergency relief and building infrastructure, in obtaining the freedom of colonized nations, and in attempting to achieve security and peace.”

On balance, he asserts, America has brought “more beneficence than avarice to the Middle East and caused significantly less harm than good.” But this optimistic grace note is contradicted by much of what he outlines in this impressive book. For as his own scholarship has shown, the Middle East has repeatedly demonstrated an infuriating ability to surprise, confound, and ultimately frustrate usually self-interested and often insensitive American plans and intentions.

Ms. Miller, a journalist living in NewYork, is the author of “God Has Ninety Nine Names: Reporting from a Militant Middle East” (Simon & Schuster).