9

The Complexities of Command: Lieutenant General Leese and Operation Olive

Late August 1944

One of General Harold Alexander’s most senior planning officers had devised a plan that involved the Americans and the British storming northward from Florence to Bologna and cutting the Gothic Line in half. Then they would flank left, right, and toward the center into the plains of Lombardy that lay along the River Po. Once Bologna had fallen, the dreaded Apennines would be behind them. They could use their tanks to best advantage in the flat countryside. This plan focused on an attack in the center, and it would be accompanied by diversionary attacks on both the Adriatic and Mediterranean coasts. The city of Rimini was the main prize in the east. But then the British commander of the 8th Army, Lieutenant General Oliver Leese, made the first of a series of strategic decisions that would ensure that the battle for the Gothic Line became a bloody, protracted affair. He insisted on attacking, and taking, the port of Rimini first.

Leese was an aristocratic British officer, the son of a baronet, who had been educated at Eton and then fought in the First World War on the Somme. He had served in the Coldstream Guards, the second-oldest regiment in the British Army. It was raised during the English Civil War in 1650 by Oliver Cromwell as part of his New Model Army, or Roundheads, who were fighting the Cavaliers, troops loyal to the monarchy of Kings Charles I and II. However, after Cromwell abdicated, the Coldstreams changed sides, backed the monarchy, helped suppress an antiroyalist revolt, and were then chosen to be the king and royal household’s personal bodyguard. By 1914, they were part of the prestigious Brigade of Guards, whose duties included guarding the monarch of England.

There was no more blue-blooded regiment in the British Army, and Leese fit in perfectly. Guards officers were not just told to think they were better; in the 1920s many of them believed it as an article of faith. Surely the award of 107 different battle honors since the 1600s couldn’t be wrong? They saw themselves as a military and social elite. Although Leese was aristocratic, he was a good leader. He was kind, enjoyed a confident popularity with his men, and was certainly brave—he was born to play the part he did. He had been wounded three times in France in the First World War, the last time on the Somme in 1916. He was decorated twice for gallantry, the second time with the Distinguished Service Order, the British equivalent of the American Distinguished Service Cross.1 He was a product of the British Empire, the upper echelons of the British class system, and was absolutely content with it. He’d never operated with any troops other than British or colonial ones. When war broke out in 1939, he was a colonel instructor at the British Army’s staff college at Quetta in India: his experiences there simply confirmed his preconceptions.

He returned home and fought with the British Expeditionary Force in their doomed and ineffectual campaign against the German invasion of France, Holland, and Belgium. He left the beaches of Dunkirk. Eighteen months of home defense in England followed, and then in September 1942, Lieutenant General Bernard Montgomery asked for him to transfer to North Africa. There, as an acting lieutenant general, he was given command of XXX Corps of the British 8th Army. Leese was not lacking in bravery, charm, connection, or leadership skills. Montgomery had instructed him at staff college in 1927 and 1928 and been impressed by him.2 Leese had an easygoing, childlike sense of humor, which British soldiers warmed to, and in the manner of the eccentric British aristocracy, developed a personal and extracurricular hobby while fighting in North Africa. He was fascinated by cacti. He made notes about the different types of cacti he found in the desert, and in the evenings when not drafting operational orders for his units, he quietly devised a way whereby, using electrically heated sand, they might be grown in large numbers in hothouses back in the chilly climate of England.

The British noncommissioned officers and private soldiers under his command, who had grown up with the divisive social realities of the English class system in the post–World War I period, understood Leese. They knew where they stood with him. The British generalship on the Western Front had so often been lackluster at best and disastrous at worst that the generation of soldiers that followed in North Africa made the most of what they had. For some of them it seemed that a quietly eccentric, amiable, and aristocratic general who had been decorated for bravery was the best they were going to get. But other nationalities, American and Commonwealth, did not warm to Leese quite so easily.

The cacti-loving officer commanded XXX Corps across North Africa and in the invasion of Sicily, after which they were sent home to Britain to prepare for the invasion of northwest Europe. Leese went with them. Then Montgomery sent him a telegram ordering him back to Italy to take over the whole of the 8th Army. For the crucial month of late August to late September 1944, the success or failure of the Allied offensive on the Gothic Line was to lie with Leese. Despite being a protégée of General Montgomery, he lacked his strategic imagination and battlefield flexibility. Along with the American 5th Army, he had led the Allied forces in the fourth battle of Monte Cassino that finally broke the gridlock south of Rome. He should, therefore, have been the perfect foil to Mark Clark, and a well-suited accompaniment and counterpoint to his command style. But he and Clark did not see eye to eye. Leese, like many British soldiers, resented Clark for his handling of the debacle at Anzio that had cost so many lives. He also resented his grandstanding entry into Rome, mistaking it for personal triumphalism instead of the collective signaling of American victory that Clark believed it to be. The two generals should have cooperated better, but Leese’s direct British superior, General Harold Alexander, was no favorite of Clark’s either. Clark had once commented that Alexander “was unsuited to high command.”3

But the most specific and focused criticism of Leese and his command style came not from the Americans but from the closest allies of the British—the Canadians.4 The Canadian commander in Italy in summer 1944, Lieutenant General Henry “Harry” Crerar, wrote in his diary about Oliver Leese and his Anglocentric view of generalship that “in practice, no Canadian, American or other national commander, unless possessing quite phenomenal qualities, is ever rated as high (in their own opinion) as the British.”

The Canadians made fabulous soldiers. Yet despite their record of dogged, tenacious, and aggressive fighting in the appalling conditions in the battles around Monte Cassino, Leese thought that their leadership was substandard. He particularly found fault with Lieutenant General Tommy Burns, the commander of the 1st Canadian Corps. This senior officer had a notoriously brusque and antisocial manner with subordinates, which led to his quick-humored Canadian soldiers nicknaming him “Smiling Sunray.” (Sunray was the radio call sign of a unit’s senior officer.) Leese was insecure about the Canadians. He thought they wouldn’t do what they were told. He thought, simply, that he was better than them. They were independent of mind and of approach to soldiering, had almost no time for the colonialist attitude of the British Empire toward its subordinates—they rightly saw in Leese a typical product of Empire—and they fiercely resented criticism. So when Leese announced that he was going to carry out an investigation into the Canadians’ (exceptional) performance in the battles in the Liri valley and on the Melfa River in May 1944, Burns and his chief of staff, Lieutenant General Ken Stuart, were incensed. Leese thought that various battalion- and brigade-level attacks could have been handled differently. The Canadians disagreed. Leese instructed Stuart to come up with a report on the capabilities of Burns and his senior officers. He said that it was likely that Burns would have to be replaced by a British general.

Not surprisingly, the Canadians closed ranks. Lieutenant General Stuart interviewed Canadian officers from brigadier down to the rank of captain and found that although the Canadians were quick to admit to tactical and logistical errors in the spring fighting—mainly based upon the appalling weather and the German tactical command of the high ground—they were an extremely cohesive division with high morale, and very determined. Stuart then turned the cards in his favor when he managed to persuade both Generals Clark and Alexander that the internal investigation was unnecessary, that the problem lay with Leese, and that the Canadians were not going to accept a British general to lead them. At a final meeting between Leese and Lieutenant-General Stuart, where the latter calmly presented his findings, Leese lost his temper and accused the Canadians of trying to take over and command the 8th Army. Secretly, even Leese knew this was far too much. He had noted frequently in his diary since the end of 1943 that he admired the Canadians’ fighting spirit and their commitment to the cause of defending the British Empire. But he could not admit to himself that on several occasions in Italy that year, a combination of the weather, the Germans’ tactical and strategic skills, their men, equipment, and control of the terrain had, simply, defeated the Allies. And he was shooting himself in both feet by criticizing the Canadians. They were one of his trump cards, some of the best troops he had.

The Canadians from New Westminster

First into the attack on Rimini were going to be the British and Canadians; the second wave would be the rugged 5th Canadian Armoured Division. One of the regiments in this unit was the Westminster Regiment, whose soldiers came from the area of the same name—New Westminster, a town just outside Vancouver in the province of British Columbia, on Canada’s Pacific coast. The Westminsters were frontiersmen—fishermen, lumberjacks, men who worked in sawmills. Above their town loomed the vastness of the mountains that march up the seaboard of the Pacific northwest. The unit sailed from Halifax, Newfoundland, in June 1941, landed eleven days later in Liverpool, and then moved to a series of training camps in southern England. The British towns and countryside were filling up with Canadians, preceding the flood of Americans who would arrive after Pearl Harbor. The Canadians were billeted in army camps and in some of the huge country houses and estates that dotted England.5 The Westminsters found themselves in countryside rather more genteel than that back home. They made camp at Pippingford Park, an English country house in the Ashdown Forest in Hampshire that dated back three hundred years to the time of King Charles II. In the woods and fields of rural Hampshire, Surrey, and Norfolk, the 5th Division spent the next two and a half years training—and so missed the disastrous baptism by fire of the Canadian army on the beaches of Dieppe in August 1942.

The Canadian generals were extremely keen that their soldiers gain combat experience and be seen to contribute to the Allied war effort. Winston Churchill, the leader of Combined Operations, Vice Admiral Lord Louis Mountbatten, and Lieutenant General Bernard Montgomery, then commanding Great Britain’s South-Eastern District, were eager to carry out an amphibious landing on the northern coast of France. It would give the Allies crucial practice for a future invasion of northwest Europe, and as Churchill said in his diaries, “I thought it most important that a large-scale operation should take place this summer, and military opinion seemed unanimous that until an operation on that scale was undertaken, no responsible general would take the responsibility of planning the main invasion.”

Marshal Joseph Stalin was exerting enormous pressure on the Allies to carry out a landing in occupied France: a year into Operation Barbarossa, he was desperate for at least thirty German divisions to be withdrawn from Russia. Allied naval intelligence reportedly wanted to use the raid as a cover so it could steal a German Enigma coding machine and codebooks from one of the headquarters in Dieppe. They’d then return it to the Bletchley Park decoding center in southern England, where the Allies had made spectacular progress in decrypting the secrets of the German Ultra system. Lieutenant Commander Ian Fleming of British Naval Intelligence—who went on to create the character of James Bond—reportedly planned this operation.

So on August 19, the raid took place. There had been a hint of doom: on August 17, in the crossword of the British Daily Telegraph, a clue appeared: “French port.” The solution appeared the next day: “Dieppe.” A senior Canadian intelligence officer, Lord Tweedsmuir, was told to investigate this apparent leak; he was the son of the author John Buchan, who had been governor general of Canada until his death in 1940. The conclusion was that the placing of the crossword clue was a coincidence. The disaster that was Operation Jubilee wasn’t.

Six thousand Allied troops, 5,000 of them Canadian, went ashore on six open French beaches at dawn, unsupported by naval gunfire. Intelligence had said the target area in and around the coastal town of Dieppe was lightly defended and its beaches suitable for landings. Within ten hours, the entire force had been either killed, wounded, taken prisoner, or withdrawn by sea. There were significant successes—British commandos destroyed an artillery battery of six 150mm guns overlooking the beaches; intelligence was gathered on radar installations; significant lessons were learned about carrying out combined operations and amphibious landings. But at every strategic and almost every tactical level, it was a failure—the Royal Navy refused to commit cruisers and battleships as fire support because they thought they would be vulnerable to air attack, and their fire would hit French civilians. Landing craft and escort vessels got confused at sea and landed in the wrong place. Of one British Commando, 750 strong, only 18 men made it ashore in the right place on Yellow Beach. On Blue Beach alone, of 556 men from the Royal Canadian Regiment who landed, 200 were killed and 264 wounded or captured. They’d planned to land under cover of smokescreens and darkness, but the first blew away, the second cleared, and they were massacred by German machine guns as they hit the beach. Three dozen valuable landing craft were lost. Tanks landed on beaches got bogged down in soft shingle.

The RAF deployed 48 squadrons of Spitfires alone, some 550 aircraft, but they were operating at the extreme level of their range, and many could spend only five minutes over the target. Of 5,000 Canadians, 3,367 were killed, captured, or wounded. Operation Jubilee was an object lesson in how not to carry out an amphibious landing. The Canadians were at the center of the furor that followed. The failure had little to do with the fact most of their troops were inexperienced—senior Allied officers determined subsequently that even the most experienced combat troops would almost certainly have proved incapable of storming open, exposed beaches in daylight covered by artillery, mortar, and machine guns. The Germans captured a set of invasion plans from an Allied officer who surrendered on a beach, and then tried—unsuccessfully—to bury his maps and documents under his feet in the shingle. German staff officers were astounded that an adversary would launch a divisional attack unsupported by artillery or naval gunfire, across exposed beaches, against an enemy that in many cases had been alerted to the forthcoming assault. Although senior Canadian officers had pressed hard for their men to be included in the plan, Canadian soldiers were left afterward with a sense of mistrust and suspicion of senior British and Commonwealth planning. So as the Westminster Regiment and the 5th Canadian Armoured Division trained for more than two years across the fields, villages, and parkland of southern England, the desperate lessons of Dieppe became ingrained in each unit’s thinking. When was the next time they’d be thrown headfirst into battle against well-prepared Germans by Allied staff officers who’d made a shoddy plan?

The Westminsters Go to War

On November 15, 1943, the Westminster Regiment set sail for Algiers. Of their six companies, A was commanded by Major John Keefer Mahony, known as “Jack.” He was born in 1911 in New Westminster, educated at the local high school, and had a reputation as an athlete. He became a journalist, reporting for the Vancouver Daily Province, before joining the Westminsters and getting a commission in 1938. He sailed for England with the rest of the unit in November 1941. Two years later, the battalion sailed to Naples from Algiers and almost immediately moved up to the front in January 1944. Over the coming months in the fighting in Italy, the Westminster Regiment established a near record of any Allied unit for the greatest number of days spent in combat on the front line. Mahony estimated that between January and April alone, when they went headfirst into the fighting on the Liri River outside Monte Cassino, it was more than a hundred. By May 3, they came out of the line after the last battle of Cassino exhausted. They had a week’s rest, and then the attack on the Gustav Line began.

Along with the rest of the 5th Canadian Armoured Division, their mission was to cross the Liri and advance up the valley that stretched between two mountain ranges northwest of Cassino. The Liri valley was the main axis of approach to Rome. Taking it was vital. The Westminsters and a Canadian armored reconnaissance unit, Lord Strathcona’s Horse, were to lead the attack with an assault over the smaller Melfa River. So on the morning of May 24, a young Canadian lieutenant from Lord Strathcona’s Horse roared forward with a troop of four light Honey tanks. Armed with 37mm cannon, these American armored vehicles had proved hopelessly outgunned in North Africa by German Panther tanks, and had made easy targets for German 88mm guns.

The tanks forded the shallow waters of the Melfa and took up positions on the west bank, facing the road to Rome. Lieutenant Edward J. Perkins and his sergeant, Clifford Macey, got the troop into defensive positions facing 270 degrees, and waited while Mahony led A Company across the river behind them to support and enlarge the bridgehead.6 The problem was that the Germans not only had machine guns, tanks, and self-propelled guns on the west bank, they also still had them on the east bank waiting to cross the river. Both these German units opened fire on A Company of the Westminsters as Mahony led them across the river on foot onto the west bank, and then as he got them positioned in a loose semicircle. The company immediately started taking casualties and, apart from the tanks’ light cannon, had almost nothing with which to hit back at the German 88s. Like the Indians and the British, the Canadians were armed with Lee-Enfields, Bren guns, and a mix of Sten and Thompson submachine guns. As German shells and bullets sang overhead, thwacked into the ground, or smashed into the rocks, the Westminsters tried to dig into the soggy ground with their entrenching tools. Mahony seemed to be everywhere, encouraging, marking targets, identifying the source of German fire.

Surrounding the small bridgehead, the Germans had two 88mm self-propelled guns, a battery of antiaircraft weapons, machine guns, and more than a hundred infantry. Against the armor, the Canadians had only cumbersome British PIAT antitank rocket launchers. They were heavy, spring-propelled drainpipes with a forward stand on which the firer rested the launcher’s weight. Thirty-two pounds, inaccurate, loathsome to carry, and requiring considerable physical strength to use, the PIAT was a disastrous invention. To cock the heavy spring, the operator had to stand up and use his booted foot to depress it, so exposing himself to enemy fire at the crucial, most vulnerable moment when he needed to reload it. The British had produced such exceptional weapons as the Lee-Enfield rifle, the Bren gun, and the 25-pounder antitank gun, but the PIAT was not one of them. However, Mahony and his men had no choice but to use the weapons they had. Using the heavy rocket launcher, they knocked out the antiaircraft guns and one of the 88s, all the while under heavy fire. Then the Germans counterattacked. A Company had crossed the Melfa 132 strong, but by this point only 60 were left unwounded. Three out of four of Mahony’s officers were wounded. At one point a section was pinned down under machine-gun fire, but the calm, levelheaded officer from British Columbia crawled forward, threw smoke grenades to cover their withdrawal, and managed to extricate the ten men, losing only one.

The Germans counterattacked again, knowing that the weakened company and the four light tanks were the only toehold the entire Allied armies had on the western side of the river. Mahony was wounded twice in the leg, as well as in the head, but overnight he commanded his company and beat off repeated German attacks, holding off the enemy until the Westminsters were reinforced and relieved the following morning. A later citation summed up the action with characteristic understatement:

Major Mahony personally led his company down to and across the river … Although the crossing was made in full view of and under heavy fire from the enemy machine-gun posts on the right rear and left front, he personally directed each section into its proper position on the west bank with the greatest coolness and confidence. With absolute fearlessness and disregard for his own safety, Major Mahony personally directed the fire of his PIATs throughout this action, encouraging and exhorting his men. Mahony was wounded in the head and twice in the leg, but he refused medical attention and continued to direct the defence of the bridgehead, never allowing the thought of withdrawal to enter his mind. His example was followed closely by his men, and the Germans were defeated in their efforts to destroy the bridgehead. His defence of the perimeter against overwhelming odds under the severest battle conditions was crucial to the outcome of the Battle of Liri Valley. Only when reinforcements arrived would Mahony allow his wounds to be dressed.7

Jack Mahony received the Victoria Cross on July 31 from King George VI. Lieutenant Perkins from Lord Strathcona’s Horse was awarded the Distinguished Service Order and promotion to captain; for a young subaltern, the award of a DSO, normally reserved for ranks of major and above, meant he had probably come close to being cited for a VC. Sergeant Macey got the Distinguished Conduct Medal. The monarch was traveling incognito in Italy, disguised as a fictitious “General Collingwood,” and other recipients of honors he handed out included Oliver Leese, whom the king knighted in the field. Mahony was still semicrippled by his wounds and could hardly stand up when George VI pinned the bronze cross with its dark maroon ribbon on his tunic.

In the Liri valley, the Canadians had led the way. But a week later, it was their turn to rest and refit as the Allied advance moved up toward Rome. The regiment was pulled back to two small villages behind the lines. As May turned to June, the late spring to early summer, A Company’s main foes stopped being enemy fire, artillery, or mines, and became diarrhea, the malaria mosquito, and jaundice. Every night, the troops would climb under an awkward mosquito net; some of them took Atabrine tablets, which caused paranoia and excessive mood swings, not behavior that self-possessed and confident Canadian combat soldiers needed.

Another persistent problem for them and all the troops on both sides was sunburn. The Mediterranean from May to September is hot, the sun unforgiving. Sun cream for Allied troops fighting in North Africa and Italy was not in regular production or indeed commercial development at that stage of the war, although Benjamin Green, an American airman who was to become a pharmacist, invented one of the first sun creams that became available only to American troops serving in the Pacific. It had a very limited protection factor and worked by blocking ultraviolet radiation. It was called Red Vet Pet (short for red veterinary petrolatum) and was akin to putting red petroleum jelly on the skin, like a scarlet Vaseline. (Coppertone acquired the patent in the early 1950s.) But for British soldiers and American GIs in summer Italy, there was little to protect their faces, arms, and necks. Olive oil was sometimes offered by sympathetic Italian civilians, which resulted in soldiers quickly finding themselves covered in a sticky amalgam of olive oil and dust, which, though hideously uncomfortable, provided some protection against the sun. On the opposite side, some units of the German army were issued a very basic white sun cream that had been developed for vacationers in the 1930s.

The weather was hot as May turned into June, and the Westminsters found streams and rivers to bathe in. There was shade under ilex and chestnut trees. Local Italians, particularly in the countryside, were beyond generous with red and white wine, apricots, melons, and peaches. Diarrhea and dysentery didn’t take orders, though, and struck constantly, so many men filled their canteens with wine rather than risk drinking water from the rivers. The stalking specter of war and fighting and combat stood back from the Westminsters for a few weeks, and looked elsewhere for victims.

The Different Allied Plans of Attack

It was no surprise the Allies couldn’t agree on a cohesive plan for the opening battle of the Gothic Line. The British leader, Oliver Leese, didn’t completely trust the commanders of one of the main component parts of his army—the Canadians—and intensely disliked his fellow army commander Mark Clark. In addition, they were making a plan to attack a well-commanded German force dug in to positions of their own choosing. Some of the senior Allied officers thought they were courting disaster. Different factors had pushed them inexorably toward a confrontation with Kesselring on a defended line on terrain of his own making. There was the failure at Anzio, Mark Clark’s entry into Rome, the invasion of southern France, and the escape northward of the German 10th Army. Now the disagreements among Clark, Leese, and the Canadians seemed to be compounding the Allies’ problems, pushing them farther into uncharted, dangerous terrain where the enemy would always blindside or second-guess them.

One thing, however, united the ambitious American Clark and the debonair but insecure British Guardsman Leese. They both deeply resented the way their armies had been stripped of seven divisions in the lead-up to the invasion of southern France, a redeployment both thought a diversionary waste of resources. By late August, the American and French forces fighting their way up the Rhone valley had not succeeded in diverting a single German brigade, let alone a division, from Normandy. In Italy, Leese and Clark knew the British and Americans were going to need every man they could get for the attack on the Gothic Line. And they were just about to lose some more of their very best fighters, men who in three months of combat had proved invaluable.

Leese, Clark, and their planning staffs had proposed a number of different attack options to General Harold Alexander. Not surprisingly, all sides disagreed. The British favored a concentration of forces on one fixed objective—a strategic modus operandi the Americans thought was the brainchild of the trench warfare on the Western Front. Clark and the Americans wanted to push directly at the weakest point in the line, probe for resistance, and then exploit their tactical successes. Leese thought that this approach had been tried twice before by Clark, with disastrous results. Once, during the American attack on the Rapido River south of Cassino, which had proved a bloodbath. And second, on a larger scale at Anzio, where the unopposed landings had provided the perfect opportunity for an immediate and flexible tactical exploitation of the battlefield situation. Instead, under Clark’s direction, the American general John Lucas had ordered his men to dig in and consolidate the bridgehead, allowing the Germans time to counterattack and turn Anzio into the five-month debacle it had proved, where the blood of some of the best soldiers in the American and British armies had been poured needlessly into the sand.

Clark’s first plan for the Gothic Line involved the British 8th and American 5th Armies attacking together in a single push northward through the Apennine mountains, from Florence to Bologna. The plans that the partisans had captured from the Germans and smuggled across the line showed that Kesselring’s weakest point was in the center around the Fulta Pass, near Bologna. So it made sense to attack there. But this scheme was rejected by Leese. He told the veteran general Władysław Anders, the legendary commander of II Polish Corps, that he wanted to fight up the Adriatic coast, while the Americans fought in the middle. He meant that he didn’t want to fight alongside Clark’s command, but this put him in a difficult command position. If he was going to attack Rimini with a separate 8th Army command, the troops at his disposal were going to be some of the most independent and idiosyncratic in Italy. Leese would command three different corps: one Canadian, one Polish, and one made up of New Zealanders and Greeks. There was some relief—the latter also contained the 1st British Armoured Division, made up of fellow Guardsmen. But the Greeks and New Zealanders were almost as independent as the Canadians and the Poles. Leese’s British sense of superiority was about to be put to the most severe test.

Anders’s Polish troops had won the final battle of Monte Cassino. Their commander had fought in Poland and Russia, had been wounded eight times, and would be decorated twenty-eight times for gallantry by ten countries, including his own. On both the Allied and German sides, the senior commanders who were alive, capable, and in control tended to have long service experience, to have been wounded in the First or Second World War, and to be decorated. On the German side, generals who enjoyed senior command also tended to be favorites of Hitler’s: even more so after the July 20, 1944, bomb attempt on his life at Wolf’s Lair in eastern Prussia. The führer’s characteristic paranoia scattered suspicion around him like ricocheting shrapnel, and many highly capable senior officers—including Erwin Rommel in Normandy—fell victim to Hitler’s revenge.

So to counter Mark Clark’s strategy, Leese proposed an alternative plan. The British 8th Army, based around its three separate corps, would attack up the Adriatic coast toward the town of Rimini. This would force Albert Kesselring to move additional forces westward from Tuscany. The Americans would then attack the center of the line, around Bologna, and a mixed multinational force—South Africans, the Nisei, newly arrived Brazilians, and a racially segregated African-American division—would advance up the Mediterranean coast in the west. The plan for the attack on Rimini was code-named “Operation Olive.” Clark and Alexander approved it. It required almost the whole of the British 8th Army to be transferred from central Italy to the west. Leese was delighted. He was finally, as he saw it, properly in charge. Like so many British officers who had served with the 8th Army under Montgomery in North Africa, he had, as one senior officer would later say, “a great deal of desert sand in his boots.”8 He missed the flexibility of movement and open spaces of North Africa.

Many British commanders were exhausted by the blood, mud, and terrain that had accompanied the winter and spring slog up Italy, by the freezing, flooded rivers, the heavily defended mountains that slowed offensive operations to a crawl and restricted the Allies’ ability to exploit their huge numerical advantage in armor. There had been precious relief with the fast summer dash north from Rome to Florence. But they pined for the desert, for its vast space that had afforded such extensive freedom of operational movement. In Italy, their operations were far more dictated by the terrain and by the German defenders who held it. If the Allies could break through the Apennines at Bologna, and outflank the Germans at Rimini, and then flank left into the wide flatlands of the Po valley, the flat terrain, and their enormous superiority in armor and air power, they could regain their tactical and strategic advantage.

Under Operation Olive, and as a compromise to the Americans, Clark’s 5th Army in the center would take control over an additional four divisions of British troops. Lieutenant General Sidney Kirkman’s XIII Corps was chosen. This strengthened army would then attack toward Bologna directly through the Apennines. Once through the mountains, the XIIIth would swing toward north of Rimini, as the 8th Army advanced to the south, trapping the Germans in a pincer. Clark would push north from Florence through the San Giorgio and Futa Passes to Bologna. Once this city was taken, the road to the Po valley would be open and the Apennines cracked, and all the German forces east of Bologna would be trapped by the Americans on the left and the 8th Army on the right. Such was the plan. Kesselring himself admitted that if Bologna fell, all of his forces to the east of it—effectively half the troops under his command—were doomed.

The Allies knew very well the enormous difficulties of attacking German defensive lines. In the winter of 1943, they had been stopped at Mignano Gap, south of Monte Cassino. The Allies had been able to advance only six miles in seven weeks, constantly stalled by the rain, the terrain, the mud, and the strength of the German opposition. A New Zealand infantry officer serving in the 8th Army, Captain Frederick Majdalany, wrote at the time, “If the cost of breaking this temporary line is remembered, and the time it took to do it, an idea may be gained of what was going to be involved when the finest German troops, the geography of Italy, and the full fury of mid-winter conspired together in defense—as now they were about to do.” He was talking about the forthcoming attack on the Gustav Line, but nearly a year later, on the eve of the attack on Rimini, and with autumn coming, conditions were the same. On May 22, 1944, an eternally optimistic Leese had written to his wife, Margaret, before the battle for another of the German defensive lines south of Rome, “Tomorrow, I hope and pray the Canadians will break the Adolf Hitler Line. Then we shall have finished with organized lines for a bit. They are expensive to deal with.”

He had the largest and toughest one yet to come.