below Wellesley’s army on the march in the Peninsula.

Wellington’s lessons in failure

‘The art of victory is learned in failures.’ It might have been said by Wellington (though in fact it was said by South American revolutionary leader Simón Bolívar). Stephen Roberts explains why.


An oft-repeated myth about the ‘Iron Duke’ is that he never lost a battle. Perhaps he never lost a major battle; more importantly, he won the one that really mattered. Before he got there, though a succession of signal military failures provided Wellington with a sharp learning curve.

Born in Ireland in 1769, it was always going to be a military life for Arthur Wellesley, who joined the 73rd Foot with an ensign’s commission in 1787.

The rise of a great commander: [below left] Lieutenant-Colonel Arthur Wellesley in 1794, when he was the 26-year-old commander of the 33rd Regiment of Foot; [Below] General Arthur Wellesley in 1804, towards the end of his period of service in India; [opposite bottom] Arthur Wellesley at the time of the Peninsular War. OPPOSITe top Plan of Burgos, the scene of frustration for Arthur Wellesley during the Peninsular War, who cursed it as ‘this damned place’.
Plan of Burgos, the scene of frustration for Arthur Wellesley during the Peninsular War, who cursed it as ‘this damned place’.

His first brush with action came during the French Revolutionary Wars (1792-1802), when the European monarchies tried to throttle the fledgling French Republic. He immediately got his first taste of defeat.

The Battle of Boxtel 15 September 1794

Boxtel was Wellington’s debut action. By now a lieutenant-colonel, he was in command of the 33rd Regiment of Foot, part of an army commanded by the Duke of York (the second son of King George III) and General Ralph Abercromby.

An attempted Allied invasion of northern France had failed, and the Allied army was in retreat, pursued by the French. The Allies formed a line on the River Aa, with a forward outpost on the Dommel at Boxtel.

French forces forded the Dommel and fell upon the rear of the Hessian contingent of Allied troops, who were severely mauled and driven back. Abercromby was tasked with recapturing Boxtel, but, on encountering his enemy, overestimated its strength and withdrew.

The Allied position disintegrated, with the Aa line abandoned, as the Anglo-German force withdrew behind the Meuse, with several forts lost. The loss of nerve at Boxtel, amid British command errors, made this an inglorious retreat.

Arthur Wellesley at the time of the Peninsular War.

Wellesley is said to have displayed ‘sang froid’ in the rearguard. The retreat could have degenerated into rout had the 33rd not stood firm (though Wellesley was not directly responsible for this). The young lieutenant-colonel – he was only 26 – ‘learned how things should not be done’.

Lessons: The need for accurate and plentiful intelligence, and for command clarity.

India, Interlude, Ireland

Dispatched to India with his regiment in 1797, Wellesley gained more experience of battle craft, and also of siege warfare, destined to play a larger part in his career.

His Indian sabbatical made him more cautious and hammered home the importance of sound logistics (later, he would ensure that his armies were better supplied and organised than those of the French, who tended to ‘live off the land’).

During an interlude back home, he served as a Tory MP (1806-1809) and became Irish Secretary (1807-1809), but he was first and foremost a soldier rather than a politician, and his great opportunity now came.

The Peninsular War 1807-1814

The rise of a great commander: Lieutenant-Colonel Arthur Wellesley in 1794, when he was the 26-year-old commander of the 33rd Regiment of Foot.

A conflict to establish control over Portugal and Spain (the Iberian Peninsula), the Peninsular War was fought chiefly between Britain and France, but with major contributions by the Spanish and the Portuguese.

The war began in 1807, when the combined armies of France and Spain occupied Portugal. Sent in to aid the Portuguese in 1808, Wellesley was briefly superseded, then reinstated the following year, when he assumed the chief command in the Peninsula, which became Britain’s principal land theatre during the Napoleonic Wars.

The war turned in 1808, when the Spanish rebelled against Napoleon’s attempt to place his brother, Joseph, on the Spanish throne. British and Portuguese forces eventually secured Portugal, thenceforward using it as a base from which to strike at the French occupation of Spain.

General Arthur Wellesley in 1804, towards the end of his period of service in India.

Wellington was assisted by Portuguese and Spanish troops, both regulars and ‘guerrillas’ (Spanish for ‘little war’, a term first used for irregular forces during this conflict).

The Battle of Pombal 11 March 1811

By the time of the skirmish at Pombal, in Portugal, Wellesley had risen to lieutenant-general. He ordered the construction (1809-1810) of the Lines of Torres Vedras to defend Lisbon from Marshal André Masséna and his 1810 offensive. It worked, as come March 1811, Masséna was in retreat from the Lines.

Pombal was the first in a series of notable rearguard actions fought by Marshal Ney. Here, he faced Wellesley and the Portuguese general Luís do Rego Barreto. The wily Ney deceived the former, manoeuvring in such a manner that Wellington assumed the French were going on the offensive again and advancing back towards Torres Vedras.

Wellington postponed his own planned offensive, due to this false intelligence, giving Masséna a vital 24-hour head-start in his retreat. When Wellesley finally got going, he found Ney waiting for him at Pombal.

above The fortified frontier city of Badajoz during the Peninsular War, the scene of no fewer than three sieges between 1811 and 1812. Wellington’s Peninsular Campaign was less a blitzkrieg of decisive battle than a see-saw of manoeuvre and positional warfare. below Picton’s 3rd Division storms Badajoz during the third siege in March-April 1812.
The fortified frontier city of Badajoz during the Peninsular War, the scene of no fewer than three sieges between 1811 and 1812. Wellington’s Peninsular Campaign was less a blitzkrieg of decisive battle than a see-saw of manoeuvre and positional warfare.

It was here that Ney turned to face his pursuers and defeat the larger Anglo-Portuguese forces. Ney had a single battalion defending the castle at Pombal, which Wellesley tried to cut off, using George Elder’s Portuguese Light Infantry and companies of the 95th Rifles to storm a bridge while British general Sir Thomas Picton attempted an outflanking manoeuvre.

Initially, the French were driven out of Pombal, but, rallied by Ney, they forced the Allies back. According to Picton, Ney’s tactics were a ‘perfect lesson in the art of war’. Ney’s rearguard then withdrew in good order under cover of darkness.

Lessons: The importance of intelligence, the value of deception, and the need for rapid concentration and movement.

The Battle of Redinha 12 March 1811

Another rearguard action the following day, Redinha saw Wellesley again lock horns with Ney, who looked vulnerable at the rear of the French column.

Picton’s 3rd Division storms Badajoz during the third siege in March-April 1812.

Although the French were outnumbered by Anglo-Portuguese forces, Ney’s resistance held the Allies at bay for a day. Wellesley proceeded with caution, knowing there were many more French divisions close by, and praised his opponents for staying in the field so long.

Wellesley refused to commit until all his available forces had concentrated, including Pack’s Portuguese and Picton’s 3rd Division, which attacked around the enemy left, while the Light Division went around the right, so that both of Ney’s flanks were threatened simultaneously. But judicious use of ‘retreat, regroup, and retreat’ enabled him to hold Wellesley at bay.

Wellesley’s attempts at outflanking having failed, he launched a frontal assault. He suffered heavy losses from French artillery fire, and the Allies were driven back.

Wellesley’s tactics were condemned by critics on both sides, the main gripe being his caution. Wellesley feared that he faced the whole French army, when, in fact, it was only a rearguard – but such an effective one that it enabled Masséna to cross the River Mondego to safety.

Lessons: Caution should not become over-caution.

The Second Siege of Badajoz 5 May-16 June 1811

Wellesley now found Spanish siege craft as tricky as pitched battle. First General William Beresford, then Wellesley, who brought in reinforcements, besieged Badajoz, which had been taken by the French in March and was defended by General Armand Philippon. Ultimately, the Allies withdrew because of a French relief effort.

below Soldiers of the 57th Foot during the Peninsular War. Long campaigning with several years of marches, sieges, and battles turned Wellesley’s Peninsular War army into one of the finest.
Soldiers of the 57th Foot during the Peninsular War. Long campaigning with several years of marches, sieges, and battles turned Wellesley’s Peninsular War army into one of the finest.

Badajoz, in south-western Spain, was a border fortress protecting one of the principal routes in and out of Portugal. Due to its strategic position, it was much fought over (four times during the Peninsula War, with the British besieging it thrice and the French once).

The May-June 1811 siege began badly. Delays in Beresford’s assault enabled the French to strengthen defences. The absence of a siege train (which could take 4-6 weeks to arrive from Lisbon) was down to Wellesley, who nevertheless ordered Beresford to invest a trio of forts, whilst bringing in more Spanish troops to guard against a relief effort.

Poor Beresford had to break off to fight a battle at Albuera (a spot chosen by Wellesley for a covering action) as Jean-de-Dieu Soult advanced on Badajoz. Beresford successfully defended his siege works and bought more time for the assault, until the French forces were able to combine and threaten to overwhelm the besiegers.

Wellesley took over from Beresford on 27 May, but soon realised what the latter had faced, suffering problems with cannon (Portuguese ‘antiques’) and siege ladders (five feet too short), and appreciating he had underestimated the strength of the defences.

Assaults by the 7th Division suffered heavy losses, whilst Wellesley was worn down by rivalry between his Spanish and Portuguese allies, and the unreliability of the Chasseurs Britanniques, who had been recruited from French opponents of Napoleon, but who either deserted or betrayed intelligence.

Wellesley was frustrated by his subordinates’ inability to deliver and the dilatoriness of his cavalry in arriving (presumably to cover his withdrawal, but also to scout and provide early warning of enemy intentions).

The siege was lifted when intelligence reached Wellesley of an approaching relief column. It was a prudent withdrawal, as the Allies would have been outnumbered by the combined armies of Soult and Auguste de Marmont, especially in cavalry.

Lessons: Avoidance of delay and the importance of effective and efficient logistics. The problems posed by unreliable allies and subordinates.

The Combat of El Bodon 25 September 1811

The skirmish at El Bodon, in Spain, was another defeat, when an Anglo-Portuguese force was bested.

Wellesley was blockading Ciudad Rodrigo, in western Spain, close to the Portuguese border, which Marmont was keen to relieve, and, as with Badajoz, Wellesley did not have the wherewithal to capture.

The Allied forward position, some three miles away at El Bodon, was occupied by Picton and the 3rd Division, which could have been overwhelmed, with Wellesley’s army spread out over some 80 miles in all.

The speed of the French advance, under Louis-Pierre Montbrun, almost caught Wellesley out. His second-in-command, General Thomas Graham, expressed his concern. Command and control failures were evident. Major Henry Ridge (2nd/5th Foot), for example, had no orders instructing him how to react if attacked.

below Wellesley’s army on the march in the Peninsula.
Wellesley’s army on the march in the Peninsula.

Wellesley arrived as British guns opened up; guns that were captured by the French, then recaptured, as fortunes swung back and forth. Ridge defied convention by attacking uphill, in line, against cavalry, driving off French dragoons and recovering the guns.

Wellesley was almost captured after mistaking French chasseurs for his own hussars.

Allied reinforcements held the position for a time, but the Allies were eventually forced to retire, doing so in square formation. Wellesley praised the steadiness, discipline, and confidence of his men, as the British infantry squares proved impervious to French cavalry, whilst Allied cavalry performed well.

Wellesley got his army safely back to Portugal, bringing the 1811 campaigning season to an end – a strategic failure.

Lessons: The strength of the British square.


The Peninsular War became a sideshow in 1812, as Napoleon prepared to invade Russia. Wellesley hoped to take full advantage of French troop withdrawals and changes of command.

Ciudad Rodrigo and Badajoz both fell. Then Wellesley targeted Burgos, in northern Spain. If he could take this too, the enemy’s forces would be cut off from their French bases.

In his most successful phase in the Peninsula, Wellesley won at Salamanca (July 1812) and relieved Madrid.

The Siege of Burgos began four days after Napoleon entered Moscow, but was again underestimated, with Wellesley treating it like an Indian hill-fort, abandoning the siege, and cursing it as ‘this damned place’, as the French closed in, just two days after Napoleon began his retreat from the Russian capital.

However, 1812 was the year the tide turned, since the French position in Spain had been permanently weakened. Wellesley would complete the job in 1813, forcing the French back to the Pyrenees.

Many fresh lessons were learned during this phase of the Peninsular War.

The Siege of Burgos 19 September-21 October 1812

An Anglo-Portuguese army, commanded by Wellesley, tried to wrest Burgos, an important supply base, from the French, whose garrison of 2,000 was led by the enterprising Jean-Louis Dubreton. Faced with French counteroffensives and a shortage of guns, Wellesley refused the Navy’s offer to land more guns at Santander, for reasons which remain hard to fathom.

He was also reluctant to mount a full- scale infantry assault after the losses at Badajoz, so his attacks were half-hearted. His sapper contingent, moreover, was seriously under-strength.

Wellesley’s attack on the San Miguel ‘horn-work’ was launched without artillery support and suffered accordingly, though the position was taken, enabling the Allies to begin digging in batteries there.

below The retreat from Burgos following another setback.
The retreat from Burgos following another setback.

The attack on Burgos proper was then ordered, but again, before any Allied guns opened up, so the result was total failure. There were insufficient scaling ladders (and they were again too short). The west wall was mined, and an advance guard tried to enter, but they were denied support and driven back.

Another mine blew a gap in the north-west wall, causing a French withdrawal from the outer defences on that side, but Wellington’s own guns were targeted, with many put out of action, whilst daring French sorties added to Allied losses.

With his guns running out of ammunition, Wellesley ordered a third mine, but the assault that followed again lacked support, and was sent in too late, by which time the French had repaired their defences.

The threat of French counter-attack finally forced the British commander to call off the siege – ironically, as extra guns Wellesley had belatedly ordered up were finally approaching.

Wellesley’s travails were not over, as there was a failure of logistics during the retreat, which led to much suffering for his army.

His withdrawal took him back to the Portuguese border, so that he ended the year pretty much where he had started: an ignominious end to what had been a glorious campaign (with notable victories at Ciudad Rodrigo, Badajoz, and Salamanca).

Wellesley blamed this latest setback on inexperienced troops and inadequate resources. It represented his most serious failure in the Peninsula.

Lessons: The need for concentration of force, including matériel, at the optimum time. The importance of artillery/infantry coordination.

The Battle of Tordesillas 25-29 October 1812

One further battle, fought in Spain, at the end of the 1812 campaigning season, concluded Wellesley’s setbacks. The French, led by Joseph Souham, were pushing the Anglo-Portuguese army back. The outnumbered Allies took up defensive positions.

Souham resolved to turn the Allied flank, audaciously getting a commando force of 55 men to swim the Duero at Tordesillas, with weapons on a raft. They proceeded to rout the Brunswickian defenders of a bridge, compromising Wellesley’s entire position, and forcing him to continue his retreat towards Portugal.

Wellesley’s logistics totally collapsed during the retreat, as his supply trains took the wrong road, forcing his men to live on acorns. There was even some insubordination, with three divisional commanders ignoring orders to retreat by a particular road.

When the Allies reached Ciudad Rodrigo, two-fifths of their number were missing.

Lessons: The value of surprise attack by elite special forces.

Bolívar may have uttered those famous words about failures leading to victory in 1816. But perhaps he had Wellington and Waterloo in mind. •

Stephen Roberts is a published author and freelance writer, with some 700 published articles in 75 different publications. He writes regularly for Military History Matters.

Arthur Wellesley

1787 – Ensign’s commission, 73rd Foot.
1794 – Battle of Boxtel (15 September).
1797 – Dispatched to India.
1803 – Victory at Assaye against French-led Marathas. Poona subjected.
1806 – Marries and becomes Tory MP, later Irish Secretary.
1809 – Assumes chief command of British forces in Peninsular War.
1811 – Battles of Pombal (11 March) and Redinha (12 March).
1811 – Second Siege of Badajoz (May-June) and Combat of El Bodon (25 September).
1812 – Napoleon invades Russia (24 June) and Battle of Salamanca (22 July).
1812 – Siege of Burgos (September-October) and Battle of Tordesillas (October).
1813 – Invasion of southern France, from Spain.
1814 – Becomes Duke of Wellington. Abdication of Napoleon.
1815 – Battle of Waterloo (18 June).
1818 – Serves in Liverpool’s cabinet (until 1827).
1826 – Constable of the Tower.
1828 – Prime Minister (until 1830).
1834 – Prime Minister for second time (Jan-Nov).
1846 – Retires from public life.
1848 – Lord High Constable of England.
1852 – Death at Walmer (14 September).

Dramatis Personae (allied)

Prince Frederick, Duke of York (1763-1827)
Second son of George III, commanded Allied forces during War of First Coalition, later reorganised British Army.

Ralph Abercromby (1734-1801)
Scottish soldier, became lieutenant-general during Napoleonic Wars.

Sir Thomas Picton (1758-1815)
Welsh officer, fought under Wellesley in Peninsula, most senior officer killed at Waterloo.

Sir George Elder (d.1836)
Scottish officer, fought in Peninsula, died in a horse-riding accident in India.

William Beresford (1768-1854)
Anglo-Irish general, marshal in Portuguese Army, fought alongside Wellesley in Peninsula.

Major Henry Ridge (d.1812)
Killed at storming of Badajoz, 6 April 1812.

Thomas Graham (1748-1843)
Scottish general, Wellesley’s second-in-command in Peninsula.

Dramatis Personae (French)

André Masséna (1758-1817)
Commander in Revolutionary and Napoleonic Wars, one of original 18 marshals created by Napoleon.

Michel Ney (1769-1815)
Commander in Revolutionary and Napoleonic Wars, one of original 18 marshals created by Napoleon, executed by French after Waterloo.

Armand Philippon (1761-1836)
French soldier, Governor of Badajoz, 1811-1812.

Jean-de-Dieu Soult (1769-1851)
French general, later Prime Minister of France.

Auguste de Marmont (1774-1852)
French general , succeeded Masséna as commander of French army in northern Spain in July 1810.

Louis-Pierre Montbrun (1770-1812)
French cavalry general, killed at Battle of Borodino.

Jean-Louis Dubreton (1773-1855)
French infantry general, mastermind of defence of Burgos, September-October 1812.

Joseph Souham (1760-1837)
French general, forced Wellesley to retreat at Tordesillas.

All images: WIPL.