Sayyidina Abu ‘Ubaydah ‘Aamir ibn ‘Abdullah ibn al-Jarrah (r.a.)

بِسۡمِ ٱللهِ ٱلرَّحۡمَـٰنِ ٱلرَّحِيمِ 

He was the image of dignity and grace; a handsome, pleasant, well-spoken man with a tall, slim physique and bright, sharp eyes.  These were the physical good looks of a man whom the Prophet (s.a.w.) said, “Every ummah has a trustee; the trustee of my ummah is Abu ‘Ubaydah ibn al-Jarrah.” 

Sayyidina Abu ‘Ubaydah was the kunya of Sayyidina ‘Aamir ibn ‘Abdullah ibn al-Jarrah (r.a.).  He was one of the ten swahabah Promised Paradise.  He remained commander of a large section of the Muslim armies during the time of the Caliphate of Sayyidina Abu Hafsw ‘Umar ibn al-Khaththab al-Faruq (r.a.), and was on the list of Sayyidina ‘Umar’s (r.a.) appointed successors to the Caliphate. 

By character and nature, he was very humble and modest.  Amongst his friends, he was gentle and soft as silk.  When it came to war, he was as hard as iron.  During the battle of Uhud, he lost his two front teeth.  It was within this battle that two of the iron links of the Prophet’s (s.a.w.) helmet pierced his head.  Sayyidina Abu ‘Ubaydah (r.a.) pulled them out with his teeth.  His integrity and honesty were unparalleled even amongst the companions of the Prophet (s.a.w.). 

Sayyidina Abu ‘Ubaydah (r.a.) was born in the year 583 CE in the house of ‘Abdullah ibn al-Jarrah, a merchant by profession.  Sayyidina Abu ‘Ubaydah (r.a.) belonged to the Quraysh clan of Banu al-Harits ibn Fihr.  Even before his conversion to Islam, he was considered to be one of the nobles of the Quraysh and was famous among the Quraysh of Makkah for his modesty and bravery.  Sayyidina ‘Abdullah ibn ‘Umar (r.a.) said that amongst the tribe of the Quraysh there were three people in whom manners and modesty excelled all others.  They also had the gift of eloquence and gentle speech.  If people looked at them, they wished to keep on looking at them.  In his opinion, the three people were Sayyidina Abu Bakr ‘Abdullah ibn ‘Utsman asw-Swiddiq (r.a.), Sayyidina Abu ‘Amr ‘Utsman ibn ‘Affan (r.a.), and Sayyidina Abu ‘Ubaydah ibn al-Jarrah (r.a.). 

By 611 CE, Prophet Muhammad (s.a.w.) was preaching the Oneness of Allah (s.w.t.) to the people of Makkah.  He began by inviting his closest companions and relatives in secret to the way of Islam.  Sayyidina Abu ‘Ubaydah ibn al-Jarrah (r.a.) embraced Islam just a day after Abu Bakr (r.a.) in the year 611.  This makes Sayyidina Abu ‘Ubaydah (r.a.) amongst the very first to embrace Islam.  He passed every trial and tribulation with flying colours.  The difficult situation created by the Quraysh was met with courage and patience.  During these times of hardship, he and the other companions of the Prophet (s.a.w.) remained steadfast.  Sayyidina Abu ‘Ubaydah (r.a.) lived through the harsh experience that the Muslims went through in Makkah from beginning to end.  With other early Muslims, he endured the insults and oppression of the Quraysh.  After the first hijrah to Abyssinia, violence against the Muslims renewed with much conviction and became stronger.  Being the only person in his clan to accept Islam, Sayyidina Abu ‘Ubaydah (r.a.) was foremost amongst them.  Prophet Muhammad (s.a.w.) suggested that the remaining Muslims who were especially vulnerable to the persecution of the people of Makkah migrate as well.  Sayyidina Abu ‘Ubaydah (r.a.) migrated to Abyssinia along with a delegation of 83 men and 20 women. 

In 622 CE, when Prophet Muhammad (s.a.w.) migrated from Makkah to Madina, Sayyidina Abu ‘Ubaydah (r.a.) followed his prophet.  When Prophet Muhammad (s.a.w.) arrived in Madina, he paired off each immigrant, muhajir, with one of the residents of Madina, answer.  Sayyidina Abu ‘Ubaydah (r.a.) was paired with Sayyidina Mu’adz ibn Jabal (r.a.), making them brothers in faith.  The Muslims remained in peace in Madina for about a year before the Quraysh raised an army to attack them. 

In the year 624, Sayyidina Abu ‘Ubaydah (r.a.) participated in the first major battle between the Muslims and the Quraysh of Makkah, at the Battle of Badr.  At the Battle of Badr, he was attacked by his father, ‘Abdullah ibn al-Jarrah, who was fighting with the Quraysh.  Sayyidina Abu ‘Ubaydah (r.a.) tried to avoid fighting him but eventually his father succeeded in blocking his path.  Sayyidina Abu ‘Ubaydah (r.a.) met his father in combat.  He defeated him and was forced to kill him.  It is as severe a test as any Muslim could face.  The following verse of the Qur'an was Revealed about this display of character by Sayyidina Abu ‘Ubaydah (r.a.): 

سُوۡرَةُ المجَادلة

لَّا تَجِدُ قَوۡمً۬ا يُؤۡمِنُونَ بِٱللَّهِ وَٱلۡيَوۡمِ ٱلۡأَخِرِ يُوَآدُّونَ مَنۡ حَآدَّ ٱللَّهَ وَرَسُولَهُ ۥ وَلَوۡ ڪَانُوٓاْ ءَابَآءَهُمۡ أَوۡ أَبۡنَآءَهُمۡ أَوۡ إِخۡوَٲنَهُمۡ أَوۡ عَشِيرَتَہُمۡ‌ۚ أُوْلَـٰٓٮِٕكَ ڪَتَبَ فِى قُلُوبِہِمُ ٱلۡإِيمَـٰنَ وَأَيَّدَهُم بِرُوحٍ۬ مِّنۡهُ‌ۖ وَيُدۡخِلُهُمۡ جَنَّـٰتٍ۬ تَجۡرِى مِن تَحۡتِہَا ٱلۡأَنۡهَـٰرُ خَـٰلِدِينَ فِيهَا‌ۚ رَضِىَ ٱللَّهُ عَنۡہُمۡ وَرَضُواْ عَنۡهُ‌ۚ أُوْلَـٰٓٮِٕكَ حِزۡبُ ٱللَّهِ‌ۚ أَلَآ إِنَّ حِزۡبَ ٱللَّهِ هُمُ ٱلۡمُفۡلِحُونَ (٢٢) 

You wilt not find any people who believe in Allah and the Last Day, loving those who resist Allah and His Messenger, even though they were their fathers or their sons, or their brothers, or their kindred.  For such, He has Written faith in their hearts, and Strengthened them with a Spirit from Himself.  And He will Admit them to gardens beneath which rivers flow, to dwell therein (for ever).  Allah will be Well Pleased with them, and they with Him.  They are the Party of Allah.  Truly it is the Party of Allah that will achieve Felicity. (Surah al-Mujadilah:22) 

In the year 625, he participated in the Battle of Uhud.  In the second phase of the battle, when Sayyidina Abu Sulayman Khalid ibn al-Walid’s (r.a.) cavalry attacked the Muslims from the rear, the bulk of the Muslim soldiers were routed from the battlefield, but few remained steadfast.  Sayyidina Abu ‘Ubaydah (r.a.) was one of them and he guarded the Prophet Muhammad (s.a.w.) from the attacks of the Quraysh soldiers.  On that day, Sayyidina Abu ‘Ubaydah (r.a.) lost two of his front teeth while trying to extract two links of Prophet Muhammad’s (s.a.w.) armour that had penetrated into his cheeks. 

In the year 627, he took part in the Battle of al-Khandaq and also in the attack on Banu Qurayzah.  He was also made commander of a small punitive expedition against the tribes of Tsalabah and Ammar who were plundering nearby villages.  In the year 628, he participated in Treaty of Hudaybiyyah and was made one of the witnesses over the pact.  Later in the same year, he was a part of the Muslim campaign to Khaybar. 

In the year 629, Prophet Muhammad (s.a.w.) sent Sayyidina ‘Amr ibn al-‘Aasw (r.a.) to Dzat as-Salasil from where he called for reinforcements.  Prophet Muhammad (s.a.w.) sent Sayyidina Abu ‘Ubaydah (r.a.) in command of an army that included Sayyidina Abu Bakr (r.a.) and Sayyidina ‘Umar (r.a.).  This was known as the “Expedition of Abu ‘Ubaydah ibn al-Jarrah”.  They attacked and defeated the enemy.  The “Expedition of Abu ‘Ubaydah ibn al-Jarrah” is also known as the “Expedition of Fish”, and the “Invasion of al-Khabat”.  It took place in October, 629 CE.  The Prophet Muhammad (s.a.w.) had sent Sayyidina Abu ‘Ubaydah (r.a.) along with 300 men to attack and chastise the tribe of Juhaynah at al-Khabat, on the seacoast, five night’s journey from Madina.  He was sent to observe a Quraysh caravan.  There was no fighting as the enemy fled after they heard of the arrival.  This expedition is famous because the Muslims were short of supply and food was running out.  They suffered from famine.  In the end, a whale was found beached and the expedition ate it for twenty days.  Shaykh Abu Muhammad ‘Abd al-Malik ibn Hisham (r.a.) mentioned the incident in great detail.  This is why it is also known as the “Expedition of the Fish”.  They brought some of that stale meat to Prophet Muhammad (s.a.w.) and he ate it also.  This was to demonstrate that the meat of the carcass is considered halal since it is from the sea.  Later in the same year, another expedition was sent under his command to locate the routes of Quraysh caravans. 

In the year 630, during the Opening of Makkah, Sayyidina Abu ‘Ubaydah (r.a.) commanded one of the four divisions that entered the city.  Later that year, he participated in the Battle of Hunayn and the Siege of Tha’if.  He was also part of the Tabuk campaign under the command of Prophet Muhammad (s.a.w.) himself.  On their return from the Battle of Tabuk, a Christian delegation from Najran arrived in Madina and showed interest in Islam.  They asked Prophet Muhammad (s.a.w.) to send them a person to guide them in the matters of religion and in other tribal affairs according to shari’ah.  Sayyidina Abu ‘Ubaydah (r.a.) was appointed to go with them.  He was also sent as an ‘amil to Bahrain.  He was present in Makkah when Prophet Muhammad (s.a.w.) passed away in 632 CE. 

The matter of succession took place at the as-Saqifah of Banu Sa’idah.  Sayyidina Abu ‘Ubaydah (r.a.) was there, along with Sayyidina Abu Bakr (r.a.) and Sayyidina ‘Umar (r.a.).  Sayyidina ‘Umar (r.a.) asked Sayyidina Abu ‘Ubaydah (r.a.) to stretch forth his hand for the caliphate but he refused.  Sayyidina ‘Umar (r.a.) then took Sayyidina Abu Bakr’s (r.a.) hand and took the bay’ah.  After the Riddah wars when Sayyidina Abu Bakr (r.a.) sent Sayyidina Khalid ibn al-Walid (r.a.) to Iraq to conquer it, he sent four Muslim armies into the Levant, making Sayyidina Abu ‘Ubaydah (r.a.) commander of one of them.  His target was Emesa.  Sayyidina Abu ‘Ubaydah (r.a.) was ordered to move through the Tabuk region after the army of Sayyidina Shurahbil ibn Hasanah (r.a.). 

He remained commander-in-chief of the Muslim armies until Sayyidina Khalid ibn al-Walid (r.a.) arrived from Iraq in 634 CE.  Sayyidina Abu ‘Ubaydah (r.a.) was ordered by Sayyidina Khalid (r.a.) to remain where he was until Sayyidina Khalid (r.a.) reached the Banu Ghassan city of Baswra, where they met.  The castle surrendered the city after the Battle of Buswra in mid-July 634 CE.  130 Muslims died in the battle.  Soon after, the Muslims learned of a gathering of a 90,000 strong Byzantine army at Ajnadayn, about 24 km southwest of Jerusalem.  All the divisions of the Muslim army, about 32,000 in number, joined Sayyidina Khalid (r.a.) at Ajnadayn on 24th July 634 CE.  Under the command of Sayyidina Khalid (r.a.), the Muslims defeated the Byzantines on the 30th July 634 CE at the Battle of Ajnadayn.  After one week, Sayyidina Abu ‘Ubaydah (r.a.), along with Sayyidina Khalid (r.a.), moved towards Damascus.  On their way to Damascus, they defeated another Byzantine army at the Battle of Yakusa in mid-August 634 CE.  Calois and Azrail, the governor of Damascus, led another army to stop Sayyidina Khalid’s (r.a.) corps but they were also defeated in the Battle of Maraj asw-Swafar on 19th August 634 CE. 

The next day, the Muslims reached Damascus and besieged the city, which continued for 30 days.  After defeating the Byzantine reinforcements sent by Emperor Heraclius at the Battle of the Pass of ‘Uqab, 32 km from Damascus, Sayyidina Khalid’s (r.a.) forces attacked and entered the city.  With Sayyidina Khalid’s (r.a.) divisions investing the city from the northeast, Thomas, the purported son-in-law of the Emperor Heraclius, surrendered the city to Sayyidina Abu ‘Ubaydah (r.a.), who was besieging the Bab al-Jabiyyah, on 19th September 634 CE. 

Sayyidina Abu ‘Ubaydah (r.a.) was appointed by Sayyidina Khalid (r.a.) to besiege the Bab al-Jabiyyah.  It was Sayyidina Abu ‘Ubaydah (r.a.) who gave peace to Damascus after Sayyidina Khalid (r.a.) attacked the city and conquered it by force.  Sayyidina Abu ‘Ubaydah (r.a.), Sayyidina Shurahbil (r.a.) and Sayyidina ‘Amr (r.a.), unaware of Sayyidina Khalid’s (r.a.) attack from the Eastern Gate, had agreed to their surrender on generous terms.  This was reluctantly endorsed by Sayyidina Khalid (r.a.).  The Byzantine army was given a cease fire of three days and allowed to go as far as they could with their families and treasure.  Others simply agreed to stay at Damascus and pay tribute.  The Muslims controlled the road to Emesa, so the Byzantines went west and then north up the Baqa’a Valley.  After the three-day truce was over, the Muslim cavalry, under Sayyidina Khalid’s (r.a.) command, pursued the Byzantine column via the shorter Emesa road and caught them in the northwest Baqa’a Valley, just before they entered the mountains en route to Antioch at the Battle of Maraj ad-Dibaj. 

On 22nd August 634 CE, Caliph Sayyidina Abu Bakr (r.a.) passed away, making Sayyidina ‘Umar (r.a.) his successor.  Sayyidina ‘Umar (r.a.) relieved Sayyidina Khalid (r.a.) from the command of the Muslim army, and appointed Sayyidina Abu ‘Ubaydah (r.a.) as the new commander.  This was done to dispel the impression that the victories were due to Sayyidina Khalid (r.a.).  Also, Sayyidina ‘Umar (r.a.) likely did not approve of Sayyidina Khalid’s (r.a.) more ruthless methods, since this was not the preferred manner of pacifying a population.  Moreover, Sayyidina Khalid (r.a.) was an overtly generous person, who according to some would often waste his money in giving gifts to his soldiers as a reward for their bravery in the battles.  Due to different style of commands, there was a slowdown in the pace of operations, as Sayyidina Abu ‘Ubaydah (r.a.) preferred a methodical advance, in contrast to Sayyidina Khalid (r.a.) who was a master of the surgical strike.  The conquest of Syria continued under the new commander.  Sayyidina Abu ‘Ubaydah (r.a.) relied heavily on the advice of Sayyidina Khalid (r.a.). 

Soon after the appointment of Sayyidina Abu ‘Ubaydah (r.a.) as commander-in-chief, he sent a small detachment to the annual fair held at Abu al-Quds, modern day Abla, near Zahle; east of Beirut.  There was a Byzantine and Christian Arab garrison guarding that fair, the size of the garrison was miscalculated by the Muslim informants and it quickly encircled the small Muslim detachment.  Before it would have been completely destroyed, Sayyidina Abu ‘Ubaydah (r.a.), having received new intelligence, sent Sayyidina Khalid (r.a.) to rescue the Muslim army.  Sayyidina Khalid (r.a.) reached there and defeated them in the Battle of Abu al-Quds on 15th October 634 CE and returned with tons of looted booty from the fair and hundreds of Byzantine prisoners. 

With central Syria captured, the Muslims had given a decisive blow to the Byzantines.  The communication between northern Syria and Palestine was now cut off.  Sayyidina Abu ‘Ubaydah (r.a.) decided to march to Fahl, modern Pella, which is about 150 m below sea level, and where a strong Byzantine garrison and survivors of Battle of Ajnadayn were present.  The region was crucial because from here the Byzantine army could strike eastwards and cut the communications line with Arabia.  Moreover with this large garrison at the rear, Palestine could not be invaded.  The Muslim army moved to Fahl.  The Byzantine army was eventually defeated at the Battle of Fahlan on the 23rd January 635 CE. 

After the battle, which would prove to be a key to opening Palestine and Jordan, the Muslim armies split up.  Sayyidina Shurahbil’s (r.a.) and Sayyidina Amr’s (r.a.) corps moved south to capture Palestine.  Meanwhile, Sayyidina Abu ‘Ubaydah (r.a.) and Sayyidina Khalid (r.a.) with a relatively larger corps moved north through Lebanon to conquer Lebanon and northern Syria.  While the Muslims were occupied at Fahl, Heraclius, sensing the opportunity, quickly sent an army under General Theodore Trithyrius to recapture Damascus, where a small Muslim garrison had been left.  Shortly after Heraclius dispatched this new army, the Muslims having finished the business at Fahl, were on their way to Emesa.  The Byzantine army met the Muslims halfway to Emesa, at Maraj ar-Rum.  During the night Theodore sent half of his army towards Damascus to launch a surprise attack on the Muslim garrison. 

Sayyidina Khalid’s (r.a.) spy informed him about the move. Having received permission from Sayyidina Abu ‘Ubaydah (r.a.), he galloped towards Damascus with his mobile guard.  While Sayyidina Abu ‘Ubaydah (r.a.) fought and defeated the Byzantine army in the Battle of Maraj ar-Rum, Sayyidina Khalid (r.a.) moved to Damascus with his cavalry and attacked and defeated Theodore in the second battle of Damascus. 

A week later, Sayyidina Abu ‘Ubaydah (r.a.) himself moved towards Baalbek, then known as Heliopolis, where the great Temple of Jupiter stood.  Baalbek surrendered to Muslim rule after little resistance and agreed to pay tribute.  Sayyidina Abu ‘Ubaydah (r.a.) sent Sayyidina Khalid (r.a.) straight towards Emesa.  Emesa and Chalcis sued for peace for a year.  Abu ‘Ubaydah (r.a.) accepted the offer and rather than invading the districts of Emesa and Chalcis, he consolidated his rule in the conquered lands and captured Hama, Ma’arrat an-Nu’man.  The peace treaties were, however, on Heraclius's instructions, to lure the Muslims and to secure time for preparation of defenses of northern Syria.  Having mustered sizeable armies at Antioch, Heraclius sent them to reinforce strategically important areas of northern Syria, like Emesa and Chalcis.  With the arrival of the Byzantine army in the city, the peace treaty was violated.  Sayyidina Abu ‘Ubaydah (r.a.) and Khalid (r.a.) thus marched to Emesa.  A Byzantine army that halted Sayyidina Khalid’s (r.a.) advance guard was defeated.  The Muslims besieged Emesa which was finally conquered in March 636 CE, after six months of siege. 

After capturing Emesa, the Muslims moved north to capture whole of the northern Syria.  Sayyidina Khalid (r.a.), acting as an advance guard took his mobile guard to raid northern Syria.  At Shaizer, Sayyidina Khalid (r.a.) intercepted a convoy taking provisions for Chalcis.  The prisoners were interrogated and informed him about Emperor Heraclius’ ambitious plan to take back Syria.  They told him that an army, possibly 200,000 strong, would soon emerge to recapture their territory.  Sayyidina Khalid (r.a.) stopped there.  After his past experiences, Heraclius, now had been avoiding pitch battles with the Muslims.  He planned to send massive reinforcements to all the major cities and isolate the Muslim corps from each other, and thus separately encircle and destroy the Muslim armies.  Five massive armies were launched in June 636 CE to roll back Syria. 

Sayyidina Khalid (r.a.), sensing Heraclius’s plan, feared that the Muslim armies would be isolated and destroyed.  In a council of war, he suggested that Sayyidina Abu ‘Ubaydah (r.a.) draw all the Muslim armies to one place so as to fight a decisive battle with the Byzantines.  As per Sayyidina Khalid’s (r.a.) suggestion, Sayyidina Abu ‘Ubaydah (r.a.) ordered all the Muslim armies in Syria to evacuate the conquered land and concentrate at Jabiyyah.  This maneuver thwarted Heraclius’s plan, since he did not wish to engage his troops in an open battle with the Muslims, where the light cavalry could be effectively used.  From Jabiyyah, on Sayyidina Khalid’s (r.a.) suggestion, Sayyidina Abu ‘Ubaydah (r.a.) ordered the Muslim army to withdraw on the plain of the Yarmuk River, where cavalry could be used.  While the Muslim armies were gathering at Yarmuk, Sayyidina Khalid (r.a.) intercepted and routed the Byzantine advance guard.  This was to ensure the safe retreat of the Muslims from conquered land. 

The Muslim armies reached there in July 636 CE.  A week or two later, around mid July, the Byzantine army arrived.  The Byzantine commander in chief, Vahan, sent Christian Arab troops of the Ghassanid king, Jabalah ibn al-Ayham, to check the strength of the Muslims.  Sayyidina Khalid’s (r.a.) mobile guard defeated and routed the Christian Arabs; this was the last action before the battle started.  For the next month, negotiations continued between the two armies, and Sayyidina Khalid (r.a.) went to meet Vahan in person at Byzantine camp.  Meanwhile the Muslims received reinforcements sent by Sayyidina ‘Umar (r.a.). 

Sayyidina Abu ‘Ubaydah (r.a.), in a council of war, transferred the command of Muslim army to Sayyidina Khalid (r.a.), who acted as a field commander in the battle and was the mastermind behind the annihilation of Byzantine army.  On 15th August, the Battle of Yarmuk was fought.  It lasted for 6 days and ended in a devastating defeat for the Byzantines.  The Battle of Yarmuk is considered to be one of the most decisive battles of history.  It was the historic defeat that sealed the fate of Byzantines; the magnitude of defeat was such that Byzantine could never recover from it.  It left the whole of the Byzantine Empire vulnerable to the Muslim invaders.  The battle was the greatest battle ever fought on Syrian soil until then and showcased the tactical skills of Sayyidina Khalid (r.a.). 

With the Byzantine army shattered and routed, the Muslims quickly recaptured the territory that they conquered prior to Yarmuk.  Sayyidina Abu ‘Ubaydah (r.a.) held a meeting with his high command, including Sayyidina Khalid (r.a.), to decide on future conquests.  They decided to conquer Jerusalem.  The Siege of Jerusalem lasted four months after which the city agreed to surrender, but only to Sayyidina ‘Umar (r.a.) in person.  Sayyidina ‘Amr ibn al-‘Aasw (r.a.) suggested that Sayyidina Khalid (r.a.) should be sent as caliph, because of his very strong resemblance to Sayyidina ‘Umar (r.a.), with them being first cousins.  However, Sayyidina Khalid (r.a.) was recognised and eventually, Sayyidina ‘Umar (r.a.) himself came to accept the surrender of Jerusalem on April 637 CE.  After Jerusalem, the Muslim armies broke up once again.  Yazid ibn Abi Sufyan’s corps went to Damascus and captured Beirut.  Sayyidina ‘Amr (r.a.) and Sayyidina Shurahbil’s (r.a.) corps went on to conquer the rest of Palestine, while Sayyidina Abu ‘Ubaydah (r.a.) and Sayyidina Khalid (r.a.), at the head of a 17,000 strong army, moved north to conquer whole of the northern Syria.  Sayyidina Khalid (r.a.), along with his cavalry, was sent to Hazir and Sayyidina Abu ‘Ubaydah (r.a.) moved to Chalcis.  Most of the areas submitted without a fight. 

With Emesa already in hand, Sayyidina Abu ‘Ubaydah (r.a.) and Sayyidina Khalid (r.a.) moved towards Chalcis, which was strategically the most significant Byzantine fort.  Through Chalcis, the Byzantines could guard Anatolia, Heraclius’s homeland, Armenia. and the Asian zone capital, Antioch.  Sayyidina Abu ‘Ubaydah (r.a.) sent Sayyidina Khalid (r.a.) with the mobile guard towards Chalcis.  The fort was garrisoned by the Greek troops under their commander, Menas.  Menas’ authority and prestige were reported to be second only to the emperor himself.  Deviating from conventional Byzantine tactics, Menas decided to face Sayyidina Khalid (r.a.) and destroy the leading elements of the Muslim army before the main body could join them at Hazir, 5 km east of Chalcis.  This became known as the Battle of Hazir, where even Sayyidina ‘Umar (r.a.) praised Sayyidina Khalid’s (r.a.) military genius.  Sayyidina ‘Umar (r.a.) is reported to have said, “Khalid is truly the commander.  May Allah have Mercy upon Abu Bakr.  He was a better judge of men than I have been.” 

Sayyidina Abu ‘Ubaydah (r.a.) soon joined Sayyidina Khalid (r.a.) at the virtually impregnable fort of Chalcis, which surrendered in June 637 CE.  With this strategic victory, the territory north of Chalcis lay open to the Muslims.  Sayyidina Khalid (r.a.) and Sayyidina Abu ‘Ubaydah (r.a.) continued their march northward and laid siege to Aleppo, which was captured after fierce resistance from desperate the Byzantine troops in October 637 CE.  The next objective was the splendid city of Antioch, the capital of the Asian zone of the Byzantine Empire. 

Before marching towards Antioch, Sayyidina Khalid (r.a.) and Sayyidina Abu ‘Ubaydah (r.a.) decided to isolate the city from Anatolia.  Accordingly, they sent detachments north to eliminate all possible Byzantine forces and captured a garrison town, Azaz, 50 km from Aleppo.  From there, the Muslims attacked Antioch on the eastern side.  In order to save the empire from annihilation, a desperate battle was fought between the Muslim army and that of the defenders of Antioch, popularly known as Battle of Iron Bridge.  The Byzantine army was composed of the survivors of Yarmuk and other Syrian campaigns.  After being defeated, the Byzantines retreated to Antioch and the Muslims besieged the city.  Having little hope of help from the Emperor, Antioch surrendered on 30th October 637 CE, with the terms that all Byzantine troops would be given safe passage to Constantinople. 

Sayyidina Abu ‘Ubaydah (r.a.) sent Sayyidina Khalid (r.a.) northwards, while he marched south and captured Lazkia, Jabla, Tartus and the coastal areas west of the Anti-Lebanon mountains.  Sayyidina Khalid (r.a.) moved north and raided territory up to the Kizil River, called Kizilirmak, in Anatolia.  Emperor Heraclius had already left Antioch for Edessa before the arrival of the Muslims.  He arranged for the necessary defenses in al-Jazira and Armenia and left for his capital Constantinople.  On his way to Constantinople, he had a narrow escape when Sayyidina Khalid (r.a.), after the capturing Marash, was heading south towards Munbij.  Heraclius hastily took the mountainous path and, passing though the Cilician Gates, is reported to have said, “Farewell, a long farewell to Syria, my fair province.  You are an infidel’s now.  Peace be with you, O Syria - what a beautiful land you will be for the enemy hands.” 

With the devastating defeat at Yarmuk, his empire was extremely vulnerable to Muslim invasion.  With few military resources left, he was no longer in a position to attempt a military come back in Syria.  To gain time for the preparations of the defense of the rest of his empire, Heraclius needed the Muslims occupied in Syria.  He sought help of the Christian Arabs of al-Jazirah who mustered up a large army and marched against Emesa, Sayyidina Abu ‘Ubaydah’s (r.a.) headquarters.  Sayyidina Abu ‘Ubaydah (r.a.) withdrew all his forces from northern Syria to Emesa, and the Christian Arabs laid siege to the city.  Sayyidina Khalid (r.a.) was in favour of an open battle outside the fort, but Sayyidina Abu ‘Ubaydah (r.a.) sent the matter to Sayyidina ‘Umar (r.a.), who handled it brilliantly.  Sayyidina ‘Umar (r.a.) sent detachments of the Muslim army from Iraq to invade al-Jazira, homeland of the invading Christian Arabs, from three different routes.  Moreover, another detachment was sent to Emesa from Iraq under Sayyidina Qa’qa ibn ‘Amr (r.a.), a veteran of Yarmuk who was sent to Iraq for the Battle of al-Qadisiyyah.  Sayyidina ‘Umar (r.a.) himself marched from Madina at the head of 1,000 men.  The Christian Arabs, when they received the news of the Muslim invasion of their homeland, abandoned the siege and hastily withdrew to al-Jazira.  At this point Sayyidina Khalid (r.a.) and his mobile guard came out of the fort and devastated the army, attacking them from the rear. 

After the battle, Sayyidina ‘Umar (r.a.) ordered the conquest of al-Jazirah, which was completed by late summer 638 CE.  Following the victory, Sayyidina Abu ‘Ubaydah (r.a.) sent Sayyidina Khalid (r.a.) and Hadhrat Ayaz ibn Ghanam (r.a.), conqueror of al-Jazirah, to invade the Byzantine territory north of al-Jazira.  They marched independently and captured Edessa, Amida, which is now known as Diyarbakir, Malatya and whole of Armenia up to Ararat and raided northern and central Anatolia.  Heraclius had already abandoned all the forts between Antioch and Tartus to create a buffer zone between Muslim-controlled areas and mainland Anatolia. 

Sayyidina ‘Umar (r.a.), for the time being, stopped his armies from further invasion deeper into Anatolia but rather ordered Sayyidina Abu ‘Ubaydah (r.a.), now the governor of Syria, to consolidate his rule in Syria.  At this point, Sayyidina ‘Umar (r.a.) was reported to have said, “I wish there was a wall of fire between us and Romans, so that they could not enter our territory, nor we could enter theirs.” 

Due to the dismissal of Sayyidina Khalid (r.a.) from the army and a famine and plague the next year, the Muslim armies were kept from invading Anatolia.  The expedition to Anatolia and Armenia marked the end of the military career of Sayyidina Khalid (r.a.).  Later that year, Arabia fell into a severe drought, and large sums of people began to perish from hunger and epidemic diseases alike, both resulting from the drought and its complications.  People numbering in the hundreds of thousands, from throughout Arabia, gathered at Madina as food was being rationed.  Soon, Madina’s food reserves declined to alarming levels; by this time.  Sayyidina ‘Umar (r.a.) wrote to the governors of his provinces requesting any relevant aid they might assist with.  One such letter was rushed to Sayyidina Abu ‘Ubaydah (r.a.), who responded promptly, “I am sending you the caravans whose one end will be here at Syria and the other will be at Madina.” 

Sayyidina Abu ‘Ubaydah’s (r.a.) caravans of food supplies were the first to reach Medina, with 4,000 camels arriving full of food.  To handle the overwhelming amount, Sayyidina ‘Umar (r.a.) appointed Sayyidina Abu ‘Ubaydah (r.a.) to distribute this among the thousands of people living in the outskirts of Madina.  Following Sayyidina Abu ‘Ubaydah's (r.a.) generous aid and efforts, Sayyidina ‘Umar (r.a.) provided 4,000 dananir as a modest stipend or token of appreciation which, he refused on the grounds that the deed was done for the Sake of Allah (s.w.t.). 

Nine months had passed since the drought and a new problem had started brewing.  The plague broke out in Syria and western Iraq; it was most severe in Syria.  When the news of plague broke, Sayyidina ‘Umar (r.a.) had been on his way for a tour of Syria but, he returned from the Syrian border as advised by his companions.  Sayyidina Abu ‘Ubaydah (r.a.) met him there and said, “O ‘Umar, do you run from the Allah's Will?” 

Sayyidina ‘Umar (r.a.) was shocked by this and replied, “Yes, I am running from Allah’s Will, but to Allah’s Will.” 

Sayyidina ‘Umar (r.a.) returned from Syria because Prophet Muhammad (s.a.w.) once instructed that one should not enter the place where an epidemic is unless it is absolutely safe.  So, Sayyidina Abu ‘Ubaydah (r.a.) returned to his army at Emesa.  It was then that a plague hit the land of Syria, the like of which people had never experienced before.  It devastated the population. As Sayyidina ‘Umar (r.a.) wanted to make Sayyidina Abu ‘Ubaydah (r.a.) his successor, he did not want him to remain in the region of the epidemic.  Sayyidina ‘Umar (r.a.) dispatched a messenger to Sayyidina Abu ‘Ubaydah (r.a.) with a letter saying, “I am in urgent need of you.  If my letter reaches you at night I strongly urge you to leave before dawn.  If this letter reaches you during the day, I strongly urge you to leave before evening and hasten to me.” 

When Sayyidina Abu ‘Ubaydah (r.a.) received Sayyidina ‘Umar’s (r.a.) letter, he said, “I know why ‘Umar needs me.  He wants to secure the survival of someone who, however, is not eternal.”  So he wrote to Sayyidina ‘Umar (r.a.), “I know that you need me.  But I am in an army of Muslims and I have no desire to save myself from what is afflicting them.  I do not want to separate from them until Allah Wills.  So, when this letter reaches you, release me from your command and permit me to stay on.” 

When Sayyidina ‘Umar (r.a.) read this letter, tears filled his eyes and those who were with him asked, “Has Abu ‘Ubaydah died?” 

He replied, “No, but death is near to him.”  Sayyidina ‘Umar (r.a.) sent another messenger to him saying, “If you are not coming back, at least move to any highland with a less humid,” environment. and Sayyidina Abu ‘Ubaydah (r.a.) moved to Jabiyyah.  Soon after, Sayyidina Abu ‘Ubaydah (r.a.) was struck by the plague. 

In Sayyidina Abu ‘Ubaydah’s (r.a.) last days, he made the following statement to the Muslims: “Today, I am giving you some advice.  If you accept it, you will find peace and security to be your companions.  Establish swalah, be regular in your prayer.  Fast during the month of Ramadhan.  Give sacrifices and be charitable often.  Perform the haj.  Perform the ‘umrah.  Encourage and instruct each other to do good actions.  Wish your rulers well and be loyal to them.  Never deceive your rulers.  Be careful that you perform your duties and not be lost in worldly pursuits.  Listen carefully to what I have to say next.  Even if a man gets to live a thousand years, one day he will be in the same position in which you see me today, no one can escape death.  My greetings of peace to all of you.  May there be countless Blessings of Allah the Merciful on you all.”  He appointed Sayyidina Mu’adz ibn Jabal (r.a.) as his successor.  He said to Sayyidina Mu’adz ibn Jabal (r.a.), “Lead the men well in prayers.  May Allah Protect you.” 

With these humble words on his lips, he returned to Allah (s.w.t.).  Sayyidina Mu’adz (r.a.) got up and said to the people, “O people, you are stricken by the death of a man.  By Allah, I do not know whether I have seen a man who had a more righteous heart, who was further from all evil and who was more sincere to people than he.  Ask Allah to Shower His Mercy on him and Allah will be Merciful to you.” 

He passed away in 639 CE and was buried at Jabiyyah.  It has been narrated that his janazah was led by Sayyidina Mu’adz ibn Jabal (r.a.).  He was given the title, Amin al-Ummah, the trustee of this ummah.  During his lifetime, he was Given the Glad Tidings that he would go to paradise by the Prophet (s.a.w.).  He was a Blessed man, indeed. 

His legacy is exemplary.  He chose to live a simple way of life, opting for the most modest of garments when compared to some of the other swahabah of the Prophet Muhammad (s.a.w.).  During the conquest of Jerusalem, when Sayyidina ‘Umar (r.a.) had come to accept the surrender of Jerusalem, he was met by Sayyidina Khalid ibn al-Walid (r.a.) and Yazid ibn Abu Sufyan.  Sayyidina ‘Umar (r.a.) dismounted from his camel and threw sand at them while admonishing them, “It has not been even a year since you have come out of the hunger and hard life of Arabia and you have forgotten all the simplicity when you saw the glamour of Syria's Emperor?” 

Both men were wearing better garments then they were previously accustomed.  Sayyidina Khalid (r.a.) noted that beneath their clothes they were still sufficiently armed, indicating they were still remembered the hard desert life, bringing some relief to the Caliph.  Sayyidina Abu ‘Ubaydah (r.a.) was also present, but had always maintained his humble dressing and way of life.  Sayyidina ‘Umar (r.a.) was pleased to see him, and that very evening, when Sayyidina ‘Umar (r.a.) arrived at his home, he saw that Sayyidina Abu ‘Ubaydah (r.a.), a man made successful war and earning him rights to much plunder, had no possessions at home except one bed, a sword and a shield.  Sayyidina ‘Umar (r.a.) said to him, “O Abu ‘Ubaydah, you could have arranged some things of comfort for yourself at home.” 

Replied Sayyidina Abu ‘Ubaydah (r.a.), “O ‘Umar, this is sufficient for me.” 

Christians of the Levant accepted Islam and were greatly inspired by Sayyidina Abu ‘Ubaydah (r.a.).  Members of the two Christian tribes, Banu Tanukh and Banu Salij, accepted Islam after the conquest of the city of Qasrin.  Moreover, there was much relief given by Sayyidina Abu ‘Ubaydah (r.a.) to the non-Muslims living as in Syria. 

Comparatively, little is known of Sayyidina Abu ‘Ubaydah’s (r.a.) family.  He had two wives.  From his wife, Hind bint Jabar, he had his son, Yazid ibn Abu ‘Ubaydah.  From his wife, Warjah, he had his son, ‘Umayr, but all of them died in childhood.  It is unknown if he had any daughters, but his male line of descendants is reported to be ended.  However, the al-Jarrah family in present day Jordan and Lebanon claim descent from Sayyidina Abu ‘Ubaydah (r.a.).



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