Behind Enemy Lines: The SOE and OSS Missions in the North
November 1944
Bogged down by the autumn rains of the Po valley in the east, blocked on the banks of the Serchio River in the west, struggling to the top of the peaks of the Apennines above Bologna in the center, the Allies’ midsummer optimism about a swift end to the war in Italy seemed to have been just that. Optimistic. The Canadians, British, New Zealanders, and Greeks had swung west into the flatlands of Lombardy immediately after the fall of Rimini on September 21. The British and Indians had taken the little Kingdom of San Marino on September 20, and by the end of the month had joined the main body of the 8th Army on the edge of the plains of the River Po. For months, the dream of flat, rolling countryside had beckoned to the desert veterans of the 8th Army. When it materialized in October, when that “one last ridge” at San Fortunato had been taken, the reality was a wet, waterlogged, and muddy anticlimax. Autumn rain swelled the rivers, the waters of the Po rose above it banks, and the Germans had dynamited many of the dikes and embankments that contained the irrigation channels of the valley. One British officer called it a “green nightmare of rivers, dikes and soft water-meadows.” One hundred thousand men and tanks found themselves advancing through slurping mud. The 8th Army had taken enormous casualties on Operation Olive, both in men and vehicles, tanks particularly. They saw that a combination of geography and the weather blocked their advance westward toward Bologna, so they moved forward the only way they could, north along the coast toward Ravenna.
In the center, the Indians had taken some of the Apennine peaks, but the Americans were stuck on the main mountain access road between Florence and Bologna. On the Mediterranean, the bad weather in the Serchio valley and the lack of experienced troops on the western flank had slowed the advance. By the end of October 1944, it was clear the Allies’ chances of breaking through the Gothic Line before the following year were decreasing swiftly. But the planning officers of the Special Operations Executive and the Office of Strategic Services saw this as an even greater incentive to arm, finance, and train the partisans behind German lines, and to prepare for the moment the Allies occupied northern Italy.
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One of their main aims was to stop the Italian Fascists and Germans from destroying the economic infrastructure of northern Italy—its hydroelectric dams, factories, agricultural production, and banks. So they made a plan, code-named “Rankin.” More SOE and OSS agents would be parachuted into the north, and partisan groups from the Ligurian coast in the west, via Turin and Milan to Venice and Trieste, would be kept strongly focused on the Allies’ main strategic and tactical objectives. The SOE and OSS planners at Monopoli, Rome, and Siena called these operations “anti-scorch.” They were determined to stop the Germans razing the economic powerhouse to the ground, making a postliberation civil war all the more likely. While the Canadians, the Marathas, and the Buffalo Soldiers were drawing a breath after a month of combat, the Allied intelligence infrastructure was already making plans for the transition from war to some form of peace.
What they most needed was a united coalition of Italian partisan and political groups in the north with whom they could operate, and so far they had chosen the Council for the Liberation of Northern Italy, or CLNAI, headquartered in Milan. The partisan advisers working with the allies in Rome and Siena, including Arrigo Paladini, told the Allies this coalition was their best chance. Keeping Communist political parties, and their attendant partisan acolytes, out of the operational mix was a priority. The Allies were also determined to stop Marshal Tito’s Yugoslav partisans from encroaching onto Italian territory: to the east, the SOE was running a network of officers and agents who operated with these guerrillas. A British lieutenant colonel was constantly present at Tito’s headquarters at Drvar, in northwestern Bosnia, keeping as firm a hold as possible on any westward territorial ambitions. The carrot they could wield with Tito was considerable: almost all of his weapons and medical and communications equipment was parachuted in from Italy by the Allies. But by the last week of October, the Russians were inside Hungary and had liberated the Yugoslav capital, Belgrade, on the 16th. The SOE mission in Yugoslavia was one of containment. For the Allies, keeping a tight hand on the troubled scruff of the northern Italian neck was vital. And the most important place in the north was Milan, and the most important people ex-General Raffaele Cadorna, the CLNAI and, by extension, Major Oliver Churchill.
The SOE agent had found that life in Milan was incredibly dangerous, complex, and fragile. He was operating under the assumed identity of a Slovenian immigrant employed by the state electrical company—Churchill’s command of Italian was flawed, and Milan was the richest, most cosmopolitan and cultured city in the country outside of Rome. He felt that he stood out like a sore thumb. SS patrols were everywhere, Italian Fascist troops strode down Milan’s elegant streets and swaggered through the piazzas, German regular army officers sat in cafés opposite the city’s sixteenth-century Duomo, sipping coffee and grappa, watching the city flow past them. The six main political parties, and their accompanying partisan bands, knew very well that by late spring of 1945, at the latest, the Allies would be across the entire country. They wanted power, they wanted to be in charge, and they wanted the money and control that would come with it. For every friend and ally Churchill had inside the CLNAI, he had another enemy. And this was before the Germans and the Italians were added to the potent list of threats.
He rarely stayed in the same place more than two nights running. In one particular week he moved six times.1 He was kept alive by the training he had received at Arisaig and the “spy school” at Beaulieu. He felt strange walking around the cosmopolitan streets of Milan in civilian clothes at a time when almost every single man, and many women of his generation, were in uniform. He also noted that in wartime Milan, most people were more smartly dressed than they were in peacetime England.
His appearance was another element of his disguise he had to work on, along with his faltering language. It was classic intelligence work. Churchill had to meet regularly with General Cadorna, his liaison officer, and with representatives of another partisan network, code-named “La Franchi,” that the Allies were supporting. He had to evaluate the latest status reports on the CLNAI’s interminable meetings, encode the results into ciphered messages, and place them in “dead-letter drops” so they could be picked up by other partisan contacts. They would then take the messages up into the mountains, where they would be transmitted by radio back to Monopoli. Once a reply was received, Churchill had to pick it up, decode it, and pass the requisite instructions back to the partisans. It was lengthy, complicated, time-consuming, and nerve-racking.
If the CLNAI decided at a meeting that they needed an airdrop of arms and explosives so they could protect a bridge or a hydroelectric dam, they would write out their list of requirements. These almost always exceeded their needs, sometimes by almost ludicrous levels. On two occasions, flamethrowers were requested. Churchill always told the partisans that their best source of heavier weapons—belt-fed machine guns, mortars—was from the Germans or Italian Fascist troops themselves. Using the enemy’s weapons against it was a simple and extremely effective technique. In any firefight, it made it impossible for the Germans to tell who was who from the sound of the weaponry being used. MP 40s and MG-42s had significantly different muzzle reports from Sten guns, Carcano rifles, Bren guns, or .45 Thompsons. An experienced soldier or partisan fighter could tell where the enemy was by the sound of its weapons: if both sides were using the same equipment, this became impossible. It was also much easier to replenish ammunition by stealing or hijacking it from enormous existing enemy supplies on the ground than by going through the incredibly lengthy and complex process of organizing an Allied airdrop.
To pick up messages from partisan contacts, Churchill went through the dead-letter drop or pickup routine. He always arranged to pick up or drop in a location like a café or a restaurant where people gathered; he’d enter, check the entrance and exit, order his aperitif or coffee, and then move to the bathroom. The message would be behind the lavatory cistern, under a tile on the floor, or tucked into the petals of a plastic flower in a vase in the corridor. Once picked up, he would settle back into the café—where he would inevitably be in sight of at least one German or Italian in uniform—and take his time with his Cinzano or grappa, his Scaloppini Milanese, his zabaglione, and his espresso, and then he’d leave. He was most vulnerable when the message was in his physical possession, but the forged SS ausweis, work identification document, he carried would get him safely past almost any checks. Once outside the café, he would use white chalk to “stripe off” a nearby rubbish bin, or the back of a bench, indicating the message had been picked up or deposited.
La Franchi network took care of his accommodation: a partisan would be in charge of arranging for a bedroom or apartment where Churchill could stay, often with other partisans or agents. The portinaia (concierge) would be a man or woman who was sympathetic to the CLNAI “cause.” When Churchill arrived at the front of the building, he was let in, told which floor and flat to occupy (only rich Italians lived in houses in cities) and the code word that would be used on the telephone if he and the other occupants needed to get out at three minutes’ notice. He was always to assume that any meeting or place of accommodation was potentially compromised—he wrote that he found meeting Cadorna highly problematic as he had absolutely no sense of security, and his behavior in public verged on the theatrical, thinking he could disguise himself simply by wearing dark glasses.2 Cadorna was very well known in Italy, and his outspokenly antifascist views made him a high-profile individual to meet in public. Churchill far preferred to liaise with Major Ferreo, the officer with whom they had parachuted in on the August drop above Bergamo.
The Different Partisan Groups
The partisan groups in and around Milan were made up of the six strongest political-military protagonists, moving from left to right on the political spectrum: Communists, the Action Party, Liberals, Catholics, the Christian Democrats, and the numerous “autonomous” partisan groups—like the Green Flame—operating in towns, mountains, and valleys across northern Italy. Churchill made two assessment trips outside the city. The first one was to Biella, a large industrial town northwest of Milan, famous for its textiles. There he met the Communist Party and the partisans attached to it, and reported back that they were effective and powerful but fundamentally untrustworthy. Churchill thought that La Franchi network and the autonomous, independent groupings like the Fiamme Verdi were the Allies’ best and most reliable operational support.
After Biella, he moved south to the Langhe area south of Turin, north of the town of Cuneo. Turin is surrounded in a semicircle by the Alps, and in the foothills and on the mountain slopes from the southwest to due north of the city partisan groups flourished and thrived. The region is made up of flat agricultural plains of corn, fruit orchards, and vineyards south of the city; to the west and southwest, steep foothills rise to four thousand feet and lead up into the Alps, which march across the horizon. Three hours by train southeast lies the strategic port of Genoa, on the Gulf of Liguria. To the west, the railway line leads along the succession of pretty seaside towns—Imperia, Alassio, Bordighera—that make up the Italian Mediterranean Riviera. Across Liguria and Piemonte—the region around Turin—there was almost no fighting between the Germans and partisans on a sustained basis. The former were being held in reserve for the fighting that the Germans knew would come when the Allies broke through the Gothic Line. In western Liguria and up toward the Alps, the German lover of Scotland, Major General Ernst-Günther Baade, held his men in a calm, semioperational check. The Highland claymore was firmly sheathed. The general knew that if he carried out violent and provocative rastrellamente actions across the mountains, he would be lucky to kill or capture ten or twenty partisans in an operation that could take a week and involve three thousand of his men and the local Italian Fascists. He also believed that reprisal actions were completely counterproductive. His main priority was to protect his strip of frontier mountains from incursions from southern France, by either Free French troops or fighters from the resistance. And along the Italian Riviera? Churchill knew from information passed from other SOE missions that the partisans were simply waiting for the word from Siena or Monopoli that the Allies were approaching along the Mediterranean coast, and that it was time to blow up the coastal railway line and take control of the docks in Genoa.
Returning to Milan in early November, he was tipped off that his cover was blown and that he should leave immediately. Not wasting time to return to the safe house, he went straight to Milan’s Centrale station and boarded a train to Como, crossing into Switzerland. He went to see Jock McCaffery, the head of SOE in Europe, at his headquarters in Berne, and made his report. The CLNAI, he said, was going to find it next to impossible to operate as a single, independent, and cohesive military force because it couldn’t decide on a single, independent, and cohesive political plan. This was their main failing. General Cadorna should take charge of the entire group, by issuing a simple, clear order. Churchill had, like so many others before and after him, from Caesar onward, realized that asking any group of Italians to make a collective decision about anything involving money, political power, and military action was pointless. They would argue themselves into repetitive stasis. Nobody had the confidence or drive to take charge. After Churchill had left Milan, he recommended that the Italian government in Rome issue a clear order to Cadorna: You’re in charge. Take power. Act. So they did. And the CLNAI in Milan promptly staged a ten-hour meeting, the upshot of which was that they preferred their ineffectual loosely democratic system. Nothing much functioned, and all sides essentially disliked and distrusted each other, but at least nobody rocked the boat. Churchill advised that each single Italian partisan group in control of a particular area should be assigned a British or American liaison officer: when the time came to put anti-scorch plans into effect, and confront the Germans and Fascists head-on, at least they could do it in a coordinated and planned way.
One reason the Italian partisans were afraid of taking autonomous direct action was what had happened in September and October in Domodossola. The town lies north of Biella toward the Italian-Swiss border and is a strategic road and railway link between both countries—it controls access to the Simplon Tunnel, which brings the main railway from Geneva to Milan. It lies in a glacial valley in the foothills of the Alps and is a center of hydroelectric power. In May, a German rasterellamento had killed two hundred partisans who wanted to establish their own independent republic on the Swiss border. McCaffery had urged caution, telling them that up against the better-armed and -organized Germans and Italian Fascists, “they should have patience and increase their hit-and-run routine, the only possible one against superior military forces far from being in disarray.”
The partisans of the glacial valley didn’t listen. In September, they occupied the valley, declared an autonomous minirepublic, making and issuing its own laws and edicts, and shipped in their own exiled leader to take charge. One of their first demands was for enormous Allied support. Could this be the first spark in a chain of uprisings that would see the partisans try to establish control of behind-the-lines northern Italy, before the Allies had properly broken the Gothic Line? The SOE and OSS didn’t think so. The “Free Republic of Domodossola” stood in territory the Allies didn’t really need—this wasn’t Milan or Turin or Genoa. But in Milan, the CLNAI differed, and once the first partisan groups—Catholics and two independent ones—had done all the spade work and formed an autonomous administration, then the Socialists, Christian and Democrats, and Communists all gave the new “Republic” their approval. They thought the Allies would come to help. They were mistaken. The only people to arrive were 12,000 SS and Italian Fascist soldiers in early October, who took precisely a week to force the 3,000 partisans back into the mountains or across the border into Switzerland. The CLNAI immediately blamed the Allies—who in turn riposted that they’d never encouraged the formation of independent, partisan-run minirepublics. It was not the vision they had for postwar northern Italy, of small areas each controlled by a different armed group. They wanted uniform control by one political and military coalition over the entire area, with as little influence by the Communists as possible. Not surprisingly, the Domodossola incident quickly worsened relations between the SOE and the partisans, and made liaison with and influence over General Cadorna and the CLNAI in Milan much harder. Into the bargain, the Allies’ advance into the north had slowed considerably, as the weather, the terrain, and the German opposition delayed them from the optimistic dash to liberate northern Italy that they had expected in the summer. The partisans suddenly started to feel isolated from the Allies’ overall plan.
Despite this, Major Oliver Churchill ended his meeting with McCaffery by reiterating that each partisan group should have its own liaison officer. Not just for the anti-scorch operations that were part of the Rankin plan, but because it was only a matter of time before the first Allied infantry units were successfully across the Apennines, through the Gothic Line, and heading into northern Italy. Delayed by mud and weather they might be, but in the east the first British and Canadian units—the Westminster Regiment among them—were approaching the outskirts of Ravenna, where partisans, an OSS mission, and an Allied commando unit were waiting to greet them. The Marathas were over the Apennines and heading down toward the city of Forli. And in La Spezia and up to Genoa, the partisans were waiting desperately for the Buffalo Soldiers, the Brazilians, the South Africans, and their American armored support to break through the Serchio valley. So as Churchill left by road for France, and thence for an aircraft back to Monopoli, the head of the SOE in Europe recommended that all SOE agents on the Rankin anti-scorch missions should be parachuted in immediately.
Karl Wolff and the SS Intelligence Network in Northern Italy
The head of the SS and Security Police in Italy in December 1944 was SS-Obergruppenführer Karl Wolff, nicknamed “Karele.” His headquarters were in Milan, which was one of the reasons Oliver Churchill had noticed that the city was crawling with uniformed SS officers. Wolff had been Heinrich Himmler’s personal adjutant, but after the death of fellow SS General Reinhard Heydrich in 1942, Himmler sent Wolff to Italy to work as a liaison officer and adjutant with Mussolini. Wolff had many priorities in Italy—the successful deportation of the Jews, looting of Jewish property and Italian artworks, commanding all SS combat troops and eventually Mussolini’s Black Shirt Fascist units, running the Gestapo’s operations against the partisans and Allied intelligence, and at one point reportedly devising a plot to kidnap the pope.3 He had several assistants who helped run a vast intelligence network across Italy. One of these was an SS-obersturmführer, or lieutenant, named Guido Zimmer.
Born in Westphalia, Zimmer was thirty-three in 1944, and an American intelligence file described him as “a slim, athletic man of average height with dark brown hair and a high-pitched voice.”4 He had joined the Nazi party in 1932 and the SS and Himmler’s SD in 1936. And in 1940, as a member of Foreign Intelligence branch of the Reich Main Security Office, or RSHA, he was assigned to Rome. But Zimmer’s cover was blown through a slip, and he was recalled to Berlin.
After the armistice, when the deportation of Jews from Italy began under the direction of Herbert Kappler, Obsersturmführer Zimmer was assigned to Genoa, where he hunted down Jews, appropriated their property and goods, and stole some of it for himself. He was responsible for SS intelligence gathering along the Ligurian coast from Genoa to the French border. He split his time between Liguria and Milan, where his immediate superior was based. SS-Standartenführer Walter Rauff was head of the Gestapo and SD for northwestern Italy and had been one of the original designers of mobile gassing vans designed to kill Jews and other concentration camp inmates. Zimmer’s agents were not only in northwestern Italy and along the Ligurian coast but also in France, Switzerland, Austria, and all over central Italy.
Zimmer was self-protecting and pragmatic, and he looked to the future, which was why Wolff increasingly involved him with a burgeoning project that, by autumn 1944, had started to take a more concrete shape since the July 20 assassination plot on Hitler. The head of the RSHA Foreign Intelligence branch, Walter Schellenberg, wanted to begin tentative peace negotiations and discussions with the Allies, who would almost certainly demand the total and unconditional surrender of the German military and political hierarchy. But if a separate peace deal could be made among the Germans, Italians, Americans, and British—specifically excluding the Russians—Schellenberg was eager to pursue it. He, like others, was keen to keep the Red Army out of central and southwestern Europe, particularly Austria. So Wolff and his staff—which included Zimmer—were under clear instructions to build intelligence contacts with Italians on all levels, Fascist, partisan, businessman, politician or, even better, any combination of these four.
In the seaside town of Savona, just west of Genoa, Zimmer’s main liaison officer with the Italian Guardia Nazionale Repubblicana, the Fascist security police, was a lieutenant colonel named Gastalde Zofferino. He gathered information about partisan operations from wherever he could, and about SOE and OSS movements from captured Italian guerrillas, Allied POWs, and Italian civilians. One of Zofferino’s main contacts in the regional town of Imperia, an olive-oil-producing port southwest of Savona, was a pro-Mussolini army officer named Vittorio Ordano. His wife, Ernesta, helped provide low-level intelligence and whatever information she could glean on partisan activities in and around Imperia, and in the mountains above it. It was, she was convinced, the best way to have some form of postwar security, when the Fascists would surely ultimately triumph. Their daughter, Paola, who was twenty, frequently disagreed and argued with her parents, and was often late arriving home in the evenings—or indeed absent. She explained to her mother that work kept her late, or she was staying with a girlfriend in neighboring Bordighera, farther up the railway line. Ernesta could never understand why food and the olives from the grove in their garden so often went missing. She wondered what else was disappearing under her nose. But as autumn 1944 came around, and the summer sun started to fade over the dark cobalt Ligurian Sea, she never dreamed for a moment that her daughter was a full-fledged partisan, operating in the mountains above the city.5
Operation Chrysler, the OSS, and the Communists
On the evening of September 27, 1944, four American soldiers from an Office of Strategic Services mission had stood on the edge of the runway at the Pisa airport. Since D-day, the strategic situation in the European war had shifted fast, and suddenly the battles on the Gothic Line, overlooked for several weeks that autumn, were once more becoming a vital part of the conflict to shape southeastern Europe. Churchill and Eisenhower had foreseen this, and Stalin knew it. One of the places where the Allies and the Red Army risked meeting first was at the very bottom of southeastern Europe, at the Trieste Gap in southern Yugoslavia. To the north, the vastness of Germany, Poland, and Hungary, and the huge German forces contained in those countries, separated the Allies in the west from the Red Army in the east. The enormous German Army Group Centre had been destroyed in mid-June in Belarus in Operation Bagration—the largest defeat in six years of Wehrmacht troops. The Russians now knew about the realities of the Holocaust after the Red Army liberated Majdanek concentration camp in late July.
While the SOE was hard at work trying to orchestrate a unified alliance in Milan, the OSS was planning to link up the partisans operating on the Adriatic coast, from Trieste down to Rimini. The next big Allied offensive on the Adriatic was going to be the attack on Ravenna in November. The British, Canadians, and Americans wanted the partisans to be united in tandem with their objectives. By mid-October, these firmly included the partisans in Yugoslavia. The SOE and the OSS were trying to prevent Marshal Tito’s men from looking hungrily westward: it was only a matter of days before the Yugoslav capital, Belgrade, would be liberated by Red Army soldiers and Tito’s partisans on the 16th. Both covert agencies knew that Tito would immediately begin looking toward Slovenia and northeastern Italy after they arrived. The Allies wanted the Ljubljana Gap—which led through Slovenia up to Austria—kept open at any cost so they could reach Vienna before the Red Army. The operational imperative to get to Ravenna—and afterward north up the Adriatic coast to Venice and Trieste—was thus increasing by the day. So there was a new front developing in the Gothic Line battles: the northeastern Adriatic front, the battle for the Trieste salient. And so, when on October 16, 1944, the Yugoslav and Bulgarian capitals of Belgrade and Sofia were liberated by the Russians, the Red Army was now only days away from the Adriatic coast, and possibly two weeks away from the crucial strategic junction of Yugoslavia, the Adriatic, and Italy. The Allies were very concerned. So the four-man mission waiting at Pisa’s airport on the evening of September 27 had been just a small part of the Allied efforts to stall efforts by Italian Communist partisans to link up with their Yugoslav comrades.
The four American soldiers from an Office of Strategic Services operation code-named “Chrysler” were parachuted into enemy territory. In keeping with official OSS orders, they were all wearing U.S. military uniforms so that if they were captured they could not be executed as enemy spies. Unlike Major Oliver Churchill, operating in civilian suits and ties in a highly specific urban environment, the four men jumped fully armed into the area around Lake Como. Their assignment was to try to unite the partisan groups in this most northern section of Italy. Once they had made contact with the guerrilla leaders, their plan was to arrange a whole series of airdrops that would arm and equip several hundred men to fight on the Allies’ side after the Battle of Ravenna, as they pushed north to Venice and Trieste.
The team’s commander was Major William Holahan, a forty-year-old lawyer who had a peacetime reserve commission in the cavalry. Accompanying him were three American Italians: 1st Lieutenant Victor Giannino, 2nd Lieutenant Aldo Icardi, and radio operator Sergeant Carl LoDolce, a Sicilian. The twenty-two-year-old Lieutenant Icardi was the only mission member able to speak the dialect of the region around Lake Como. Along with a submachine gun, pistol, hand grenades, medical equipment, ammunition, and other supplies, Holahan was carrying $16,000 worth of gold coins, U.S. dollars, and Swiss and Italian money to finance their mission. They took off just before the sun set on September 27.6