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Authors: Hugh Wilford

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Nonetheless, the Americans were not prepared to concede the Middle East entirely to their European allies, especially after the good show that Bill Eddy had put on in French North Africa. As early as the summer of 1942, Bill Donovan had proposed a plan for setting up an OSS station in Cairo to serve as a base for independent US operations in the Balkans and for sending an expedition to Lebanon to establish an American intelligence presence in the Middle East itself. Having gained the enthusiastic approval of the president, Donovan handed over the mission to Colonel Harold B. Hoskins, a textile executive with extensive Middle Eastern experience. Hoskins was a cousin of Bill Eddy, and the two men were cut from the same cloth, both Lebanon-born sons of Protestant missionaries and educators, Princeton graduates, and former marines. Hoskins’s plan for Expedition 90 was premised on the assumption that, thanks to its past reputation for disinterested benevolence in the Arab world, the United States was in a far better position than its European allies to compete with the Axis powers for Middle Eastern hearts and minds. As a State Department telegram to the American ambassador in London explained, Hoskins envisioned that the expedition’s headquarters in Beirut, supported by subsidiary stations throughout the Middle East, would orchestrate a massive campaign “of political warfare and of propaganda” specifically appealing to the unique history “of American missionary, educational, and philanthropic efforts” in the region. The mission would perforce cooperate with other Allied powers, but it was to operate “as an independent American organization and not . . . as a ‘front’ for the French and British.”
8

Not surprisingly, London did not take to Hoskins’s plan. “It was, perhaps, an odd document to be shown to an Englishman,” remarked
the laconic Sweet-Escott. “Its main burden was that the British had done nothing for the Middle East and were, therefore, completely discredited throughout the Arab world.” British apprehensions increased further when it was reported that the State Department was encouraging Hoskins to travel throughout the whole region and report back to Washington on political as well as intelligence matters. Interestingly, it was Kim Roosevelt’s admirer, Sumner Welles, who was reputed to be behind these moves; Hoskins’s Expedition 90 team included Welles’s son Benjamin, Kim’s Harvard classmate. Eventually, a combination of British foot-dragging and interdepartmental disagreements on the American side led to the quiet abandonment of the Lebanon station idea. Nevertheless, the irrepressible Hoskins still went on his tour in November 1942, provoking so many complaints that eventually Bill Donovan had to rein him in.
9

The British were less successful at halting the American plans for an OSS station in Cairo. These culminated in May 1943 with the arrival in Egypt of Stephen B. L. Penrose Jr. Although not of Middle East missionary stock himself, Penrose was the next best thing: the son of the president of Whitman College, a small college founded in Washington state by New England missionaries. After spells of teaching at the American University of Beirut (where he would later return as president) and helping direct the Near East College Association in New York, Penrose had joined the coordinator of information’s office in April 1942. He set off for Egypt the following year with “instructions to establish intelligence-gathering services in the Middle East.”
10

The task facing Penrose, a hard-driving worker with a wry sense of humor, was a daunting one. The Axis forces in North Africa had finally just surrendered, and the British were now able to focus on protecting their colonial regime from other threats. Although Anglo-American relations were often good on a personal level, the British Centre Cairo jealously guarded its agent networks and other local intelligence assets. “They were so sophisticated that they worked a great deal through the coffee shops and all sorts of things like this which were quite beyond us with our small staff,” recalled Jane Smiley Hart, a Dartmouth graduate recruited by OSS/Cairo in June 1944 as a desk clerk (and later wife of eminent State Department Arabist Parker T. Hart). Security was another concern for the new station, which operated out of the basement of an ornate villa on Rustum Pasha Street; when given the address, taxi drivers would reputedly respond, “Oh, you want the secret intelligence
headquarters!” Unfortunately, while Hart “realized that we were . . . inexperienced and had to be very discreet indeed,” other American recruits failed to grasp the need for absolute secrecy. “Sometimes I can understand why the British think we are a bunch of enthusiastic amateurs,” observed Stephen Penrose bitterly, after a “cluck” traveling from the United States “never once attempted to cover the fact that he was an OSS man.”
11

There was also the challenging environment of wartime Cairo itself, beginning with the usual inconveniences facing Westerners: “The heat, the dirt, the lack of modern plumbing . . ., the fact that not only the language but the alphabet and numbers are strange,” as Kim Roosevelt summarized them. Added to these were the peculiar strains of clandestine war work, what Jane Hart called “the complications, the constant movement, our overall fear.” For Hart, the atmosphere of the Egyptian capital had a surreal quality, very like that portrayed by the British novelist Olivia Manning in her semi-autobiographical
Fortunes of War:
“a strange mixture of glamour and long hours of hard work and very little sleep. And a great cloud hanging over our heads all the time, [as] we didn’t really know what was going to happen.”
12

For all the problems confronting him, Penrose did have some resources on which to draw. To begin with, he had his own Arabist connections in the missionary and educational worlds. Shortly after arriving in Egypt, Penrose sent for several old colleagues at the American University of Beirut to join him in the command structure of the new OSS station. These included Archie Crawford, who became his chief assistant, and David Dodge, the great-grandson of AUB founder Daniel Bliss. Missionaries, meanwhile, were a potential reservoir of field agents. While still based in Washington, Penrose had leveraged his contacts on several American missionary boards for intelligence purposes, obtaining street maps of Kuwait, for example, and grooming a young evangelist about to depart for Iran to gather “whatever information” he could. He therefore already had a rudimentary espionage network in the field when he arrived to take charge in Cairo. Finally, one other group of private US citizens on the ground had expert local knowledge and unusual freedom of movement around the region. Ironically, it was the British who had pioneered the role of archaeologist-spy: T. E. Lawrence had used excavations at the Syrian site of Carchemish as a cover for surveying the new Berlin-Baghdad railroad before World War I. Now it was
the turn of American archaeologists—who during the interwar period had established a presence in the Middle East to rival that of the British—to emulate Lawrence’s example. Indiana Jones, it seems, was not a complete invention.
13

SUCH WAS THE SITUATION THAT
greeted Kim Roosevelt when he arrived in Cairo at the beginning of 1944. Thanks to his earlier travels, “dirt and germs were nothing new” for him, he recalled later, and “the Middle East came as no shock.” Quite the reverse, in fact: like his father before him, Kim positively enjoyed the sensation of “what was formerly an abstract appreciation,” based on “travel literature,” gradually acquiring “real meaning.” He also made a point of engaging in “frequent contact with local people,” an approach that contrasted with “the isolationist views of the average American soldier.” The latter attitude he blamed largely on army doctors, whose lectures to troops about the medical risks of fraternizing struck him as excessively alarmist, not to mention offensive to the local population. He was particularly irritated when a boorish medic whom he was accompanying on a US Army goodwill trip to Jeddah (Kim “had other business” in the Saudi Arabian city and was “along for the ride”) upset the Arab hosts of a banquet held in the Americans’ honor by loudly advising his companions not to touch any of the dishes in front of them. Kim tucked in with extra gusto. “Our prestige is clearly strong enough to survive an occasional descent of this sort,” he wrote in his official report on the trip, “but I can see no satisfactory reason why it should be subjected to such a strain.” Still, for all the cultural sensitivity Kim Roosevelt displayed in his dealings with Arabs during his 1944 Egyptian mission, there was not quite the same sense of romantic stirring that had accompanied Archie Roosevelt’s first posting in the Arab world. Kim “found the land and people stimulating, full of challenging differences, encouraging and discouraging similarities,” but he had not fallen in love, at least not yet.
14

Kim’s assignment in Egypt with SOPHIA, the OSS project for placing intelligence officers under cover of James Landis’s economic mission, was a kind of covert version of Harold Hoskins’s Expedition 90, and as such it involved considerable travel around the entire Middle East. From the point of view of his future career with the CIA, Kim’s most significant sortie from Cairo occurred in March 1944, shortly after his Jeddah
trip, when he flew to Allied-occupied Iran, ostensibly as a member of an economic team led by Landis. Landing in Tehran, a strategically crucial funnel of Lend-Lease aid to the beleaguered Soviet Union, the first thing Kim noticed was Red Army troops guarding the air field. After a few days of economic diplomacy and sightseeing in the city’s bazaars, the “mysteriously undefined” Kim Roosevelt (as he himself put it) met secretly with a local OSS field agent, Joseph M. Upton, for a briefing on the US intelligence effort in the country as a whole.
15

Upton was a Harvard-educated expert on Persian antiquities, and he was apparently in Tehran overseeing archaeological excavations by New York’s Metropolitan Museum of Art. As such, his OSS cover was typical for the country. T. Cuyler Young, another operative based in Tehran, specialized in Persian language and history at Princeton University, eventually chairing that institution’s Oriental Studies Department. A third OSS agent, Donald Wilber, had majored in art and archaeology at Princeton before embarking on a scholarly career in which he won note as an authority on Persian architecture. Wilber monitored German and, increasingly, Soviet activities in Iran while researching books on Islamic monuments of the Mongol period and Persian gardens. During one expedition to spy on Red Army troop movements in Azerbaijan, he visited a village reputed to contain the tomb of a Mongol ruler and stumbled on a particularly fine Seljuk dome chamber. His excitement at the discovery was tinged by fears that the village was also home to a nest of German agents.
16

After further meetings with another OSS agent (“Roger Black,” likely a pseudonym for T. Cuyler Young), and a side trip to Iran’s beautiful old capital, Isfahan, Kim Roosevelt flew back to Cairo, where he was soon joined by a familiar face, that of his cousin Archie Roosevelt. Archie’s return to the field after his expulsion from French North Africa had not been easy. He was still “owned” by military intelligence, G2, and, although the army blocked a request by the OSS research and analysis division for his services, it otherwise seemed unsure what to do with him, sending him back to military training camp, where, between comically inept drills, he studied Arab history and taught himself Hebrew. During an interview about possible postings in the Middle East, a G2 officer asked Archie whether he was “impartial on Arab questions.” His response probably did not help his cause: “I think I am as impartial as possible,” he said, “but as an aspiring orientalist I naturally have some
sympathy with the Arabs.” Eventually, G2 relented, and after further training by area specialists with Middle East experience, Archie was assigned to military intelligence in Cairo, well away from the French. He embarked from Miami in April 1944, shortly after learning from a civilian doctor in New York that he had a “systolic murmur,” a heart condition that would have gotten him discharged if discovered in an army medical exam. He did not tell his superiors.
17

In Cairo, Archie found himself under the supervision of another Middle East–raised American, Major Edwin M. Wright, “a former missionary and later an archaeologist in Southeast Turkey, Iraq, and Iran,” as Archie described him. He also had the opportunity to reacquaint himself with his old North African travel companion Hooker Doolittle and with the Tunisian nationalist Slim Driga, now a fugitive from French justice, who introduced him to another exile, the famous Rif tribal leader and rebel ‘Abd al-Krim. Most consequential of his meetings in Cairo, though, was Archie’s reunion with his cousin Kim. “I have really grown very fond of him,” Archie wrote his wife, KW, in June. “In spite of a certain small weakness I mentioned,” he continued, with tantalizing vagueness, “[Kim] is a great solace and one of the few people I have confidence in 100%. . . . He does not, I think, go off the deep end, make stupid blunders, . . .,
etc.
as do so many people in this difficult atmosphere, and he is one of the infinitesimally small number of people I take with me in some of the more delicate interviews, without qualms.” A glowing tribute (excepting the mysterious qualification), this statement nonetheless implies that, at this stage in their professional relationship, Archie saw himself as the senior partner.
18

Archie’s field of responsibility for military intelligence was the Levant states and Palestine, and he therefore was in Cairo itself only rarely, spending most of his time traveling around the eastern Mediterranean. As was his wont, Kim came along for the ride. Early one May morning, the Roosevelts left Cairo, drove through the Sinai desert, and arrived in Jerusalem just as the light was fading, unsure whether they felt more like pilgrims or crusaders as they approached the Holy City. Clearly the younger cousin was the one calling the shots. Using his “excellent contacts,” Archie (as he wrote in his memoirs) “got into the swing right away,” and the cousins “were soon swamped with interviews and invitations.” High on their list of people to see were intelligence officers of the pre-Israel Jewish authority, the Jewish Agency, which was conducting its
own clandestine war against the Axis powers. These included a tousled-haired “kibbutznik,” the future mayor of Jerusalem, Teddy Kollek, who guided them on the next leg of their journey past the shore of the Sea of Galilee, up the Golan Heights, and into Syria. En route, they spent the night at Kollek’s kibbutz and attended a banquet at which Jews dined with Arabs. After the “green oasis” of Damascus, it was on to Beirut, where Archie delighted the guests at an OWI party by addressing them in Arabic.

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