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Authors: Hugh Wilford

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Learning the Game

I’ve read of the East for years unnumbered
,

I’ve dreamed about it since first I slumbered
,

I’ve learned about it in poems and verses
,

I’ve heard of its comforts, and heard of its curses
,

I’ve talked about it with men who’ve been there
,

I know of the trouble, and dirt, and sin there
,

And yet, on putting the facts together
,

I still want to go there as much as ever
.

—Kim Roosevelt (age fifteen), “The Lure of the East”
1

WHEN IN JULY 1953 KERMIT
“Kim” Roosevelt entered Iran under a false name to carry out perhaps the best-known CIA covert operation of the early Cold War era—the coup that toppled Iranian prime minister Mohammed Mosaddeq—it was not the first time he had pretended to be someone else. About thirty years earlier, when some childhood illness had kept him home from his New England prep school, he had entertained himself by regaling an elderly tutor with, as he recalled later, “story after story” about his “(wholly imaginary) childhood in India.” Occasionally, he would apparently forget himself and “throw in a phrase in Hindustani” for effect. One day, though, the old man remarked to the boy’s mother, “What a wonderful childhood” young Kermit must have had, “living in Lahore,” and his “little ploy was exposed.”
2

The childhood Roosevelt was claiming for himself belonged not to a real person but rather to a fictional character, the eponymous hero of the 1901 novel
Kim
, by British author and poet Rudyard Kipling. Set in British Northwest India in the late nineteenth century, Kipling’s book tells the story of Kimball O’Hara, the orphaned son of an Irish soldier and a nursemaid who grows up on the streets of Lahore living on his considerable wits. Hungry for adventure, and capable of passing as a native, Kim attaches himself to a Tibetan lama as he wanders in search of a holy river. While on this quest, the clever but mischievous young hero joins in the “Great Game”—the nineteenth-century contest between the British and Russian empires for strategic control of central Asia—by spying on behalf of an English intelligence officer, Colonel Creighton. The action culminates in the Himalayas, where Kim fights Russian agents and makes off with vital documents for the British. Recovering from his ordeal, he learns that the lama has found his river. Now a man himself, Kim faces a choice between carrying on his own quest for spiritual enlightenment or continuing to play the Great Game.

Young Kermit Roosevelt was by no means alone in his love of
Kim:
the book was immensely popular with audiences in both Britain and America, earning its author the Nobel Prize in 1907. Indeed, it still fascinates readers today, although admiration for Kipling’s literary accomplishments, including the vibrant color of the Anglo-Indian characters and locales he evokes, is tempered by acknowledgment of the imperialist assumptions underpinning his story, as well as his sometimes demeaning portrayal of “Orientals.” For the critic Edward Said,
Kim
was the supreme literary expression of Orientalism, a Western tradition of perceiving and portraying the “East” based on its colonial subjugation.
3

There was, though, something unusual about the intensity of Kermit Roosevelt’s identification with Kipling’s hero. This was apparent not just in the prank he played on his tutor but also in the firmness with which his boyhood nickname of Kim stuck to him, so that as an adult he was still widely known by it. (This book will adopt the same practice, referring to him as Kim Roosevelt, partly in order to help the reader distinguish him from his father, also named Kermit.) The abiding hold of Kipling’s story on the imagination of young Kim Roosevelt provides a revealing clue about the distinctive social and cultural background that shaped the future intelligence officer and would later exercise a crucial influence on CIA operations in the Middle East.

BORN IN BUENOS AIRES IN
1916, Kim Roosevelt was the son of the businessman, writer, and adventurer Kermit Roosevelt and Belle Willard, whose family owned numerous properties in and around Washington, DC, including the famously opulent Willard Hotel, near the White House. From his infancy, though, it was the identity of Kim’s grandfather, not that of his parents, upon which people first remarked. Theodore Roosevelt, twenty-sixth president of the United States, dominated American culture more than any other member of his generation, and it was therefore hardly surprising that, even after his death in 1919, he should have loomed large in the lives of his grandchildren.

For Archie Roosevelt Jr., Kim’s cousin and later colleague in the CIA, TR was “our hero and our playmate.” TR’s home on Sagamore Hill in Oyster Bay, Long Island, was stuffed with souvenirs of travels in faraway lands, a magical place of childhood adventure. Kim, whose father built his own family home, Mohannes, next door in Oyster Bay, had particularly fond memories of childhood Christmases at Sagamore: “Father carving the roast piglet, . . . the tree in the North Room, . . . [and] spirited, if somewhat murderous, games of field hockey down by the barn.” Years later, in 1960, Kim took his two eldest sons to East Africa and reenacted a safari his grandfather and father had undertaken there in 1909. Following the same trails, hunting the same game, even striking the same poses in photographs, Kim developed “an ever growing understanding of, and . . . a sense of intimacy with, TR himself.” For generations of Roosevelt men, the ghost of the president and paterfamilias, larger than life even in death, was never far away, a benign presence but also one capable of arousing feelings of inadequacy and loss.
4

This is not to say that Kim’s father, Kermit, was without impressive qualities of his own. Among his male siblings (Theodore Jr., Archibald Sr., and Quentin), Kermit was the most attractive—a slender, handsome young man talented as an athlete and raconteur. The East African safari with TR in 1909 also revealed him to be a brave and resourceful travel companion, a reputation confirmed five years later, when he and his father undertook an even more arduous expedition in Brazil exploring the previously uncharted Rio da Dúvida, or River of Doubt. TR nearly died in the Brazilian jungle, only making it out alive thanks to the grim courage of his son. Kermit described the earlier safari and later trips to the Himalayas and Burma with his brother Ted in published travelogues that met with considerable literary success. Among their admirers was
Rudyard Kipling himself, a family friend and frequent dinner guest of the Roosevelts, who corresponded extensively with Kermit.

It seems that Kim Roosevelt inherited at least some of his love of travel and exploration directly from his father. He was, he recalled later, “brought up” on his father’s stories of his “fabulous, adventurous trips.” Most relevant of these stories to Kim’s future career was Kermit’s account of his service in World War I. Urged by their bellicose father, whose charge up Kettle Hill in the 1898 Spanish-American War was his generation’s most spectacular act of martial valor, TR’s sons vied with one another to prove themselves in the Great War. The eldest, Ted, took an early lead by helping set up an officer-training camp in Plattsburgh, New York, before Woodrow Wilson had officially ended American neutrality, and then embarking for France as soon as war was declared in April 1917. He was soon joined by Archie and Quentin. For the debonair Kermit, however, the western front lacked romance. Instead, it was the “Orient” that beckoned.
5

In the early twentieth century the United States had almost no political or military presence in the Middle East. The dominant powers in the area were the centuries-old Ottoman Empire, with its capital in Istanbul (still known in the West as Constantinople); the British; and the French. At first, Britain had backed the Ottomans as a way of checking the Russians in the Great Game and safeguarding land routes to India, the “jewel in the crown” of the British Empire. By the time of World War I, however, local nationalist rebellions had badly undermined Istanbul’s rule, and the British, who already controlled Egypt and its invaluable strategic asset, the Suez Canal, were muscling in on the oil-rich Persian Gulf. (The French, meanwhile, dominated most of North Africa west of Egypt and were casting covetous glances toward Ottoman possessions in the eastern Mediterranean, or Levant.) After the Ottomans entered the war in alliance with Germany in 1914, Britain and France opened several new overseas fronts, including one in Mesopotamia (modern Iraq). Two years later, the British began furnishing support to an Arab uprising against Ottoman rule, known as the Arab Revolt. The United States, in contrast, never declared war on the Ottoman Empire, even after coming in on the side of the British and French.

“Wouldn’t it be wonderful to be at the fall of Constantinople?” Kermit Roosevelt wrote his father in 1917. “The whole thing appeals to me much more than trench warfare.” TR sympathized with his son; as a younger man he, too, had been fascinated by the Middle East, regarding
it in classic Orientalist fashion as a place of ancient greatness and present-day decadence, an impression apparently confirmed when he had toured the region on horseback in 1872. He also thoroughly approved of Britain’s influence in the Arab world, declaring during a return trip to Egypt in 1910 that the British were improving “the seventh century so as to bring it somewhere within touching distance of the twentieth,” a “high and honorable” task that “only a great and powerful nation could attempt.” Now, eager to see all his sons at war, TR contacted British prime minister David Lloyd George, who gave special permission for Kermit to join up with the Mesopotamian Expeditionary Force, with the rank of captain. Rudyard Kipling, perhaps sensing that the focus of the Great Game was shifting from India to the Middle East, was thrilled by this development. “Hurray!” he wrote Kermit. “We must catch people now where and as we can. . . . Come along!”
6

Landing in the southern Iraqi city of Basra, Kermit was instantly enthralled by the sights and sounds of the bazaar, which (as he recalled in his 1919 memoir,
War in the Garden of Eden)
seemed to him to possess an “intangible something,” an “ever-present exotic.” Like many earlier Western visitors to the Middle East, the young American arrived feeling a strong sense of familiarity with the region, thanks to having read about it since his childhood in
The Arabian Nights
. Kermit was therefore gratified to observe a bazaar booth “festooned with lamps and lanterns of every sort, with above it scrawled ‘Aladdin-Ibn-Said.’” From Basra it was on to Baghdad, where echoes of the
Arabian Nights
multiplied (“when the setting sun strikes the towers, . . . one is again in the land of Haroun-el-Raschid”), and from there to the ancient Mesopotamian capital of Samarra.
7

Already an Anglophile, Kermit quickly adapted to British officer culture, hiring an Arab batman and a Sikh groom. He also consorted a great deal with the political officers of the Arab Bureau, a unit of Middle East specialists—scholars, linguists, and explorers—who roamed the region providing the British authorities with crucial strategic intelligence. With their arcane yet profound knowledge and aura of exotic adventure, these British “Arabists” seemed like Kipling characters come to life, and Kermit, who himself rapidly became fluent in Arabic, lost no opportunity to quiz them, especially the brilliant Gertrude Bell, the Bureau’s only female officer. As befitted a son of Theodore Roosevelt, he also saw more than his share of actual combat, earning a British Military Cross in August 1918 for capturing an Ottoman platoon outside
Baghdad. His waggish account of stumbling on a Turkish general’s “field harem” delighted Kipling, who declared that this action deserved “either a court martial or a V[ictoria].C[ross].,” before asking, somewhat pruriently, “How did you explain to the wife?”
8

From the point of view of his son Kim, Kermit’s most exciting encounter of the war likely came after the Ottoman cause had collapsed and he was returning west to join the US Army in France. Passing through Cairo, where the Arab Bureau was headquartered, Kermit met a British colonel, “scarcely more than thirty years of age, with a clean-shaven, boyish face,” who recounted his recent experiences organizing Arabian tribes into bands that raided Turkish outposts and blew up railroads. T. E. Lawrence was not yet Lawrence of Arabia, the international celebrity created by American journalist Lowell Thomas during the 1920s, and it is therefore all the more poignant to read Kermit Roosevelt’s 1919 word portrait of this “short and slender” British officer: his habit of dressing in “Arab costume,” his hatred of “killing the wounded,” and his admiration for the Arabs, “their virility—their ferocity—their intellect and their sensitiveness.” (There is also the unforeseen irony of Lawrence’s reported remark that “he couldn’t last much longer, things had broken altogether too well for him, and they could not continue to do so.”) Kermit’s description of Lawrence, with its Kipling-esque connotations of spying and passing as a native, must surely have fired the imagination of young Kim.
9

Kermit and Lawrence carried on corresponding after the war, as the latter waged a campaign in the British press for a Middle Eastern settlement favorable to the Arabs. Lawrence’s vision did not materialize. Instead, the victorious European powers effectively carved up the Ottomans’ Arab possessions between them, the French adding Syria and Lebanon to their colonial possessions in North Africa, the British acquiring control of Palestine, Transjordan, and Iraq. Lawrence retreated into obscurity, enlisting in the Royal Air Force (RAF) under an assumed name. Still, the type of nomadic intelligence officer he had helped model during World War I became crucial to Britain’s administration of its new Middle Eastern mandate. During the interwar period, often referred to as “Britain’s moment in the Middle East,” London created what one historian has described as a “Covert Empire” in the region, reinforced on the ground by a loose network of roving Arabist spies and from the sky by RAF surveillance and occasional bombing. Meanwhile, Lawrence
himself never lost his appetite for intelligence work, migrating to the original theater of Kipling’s Great Game, India’s northwest frontier, in the late 1920s, from where he wrote Kermit Roosevelt, with evident relish, “The pot fairly boils, over Kabul way.”
10

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