How old is English?

 

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Proposed timeline

for the 5th century

 

406 A man is elected emperor of the Praefectura Gallica (Spain + Gaul + Belgium + Britain) by unpaid legions in Britain. He adopts the name Constantine III, which announces a program similar to Constantine the Great. He reinforces the local tax administration, raises the tax ratios and departs with most British troops to the Continent to impose his authority in Gaul.
408 The tax administration in Britain is deposed by local lords who are fed up paying for futile continental ambitions while they are left without a proper protection at home. Apart from that, Constantine is not a member of the 'proper' class. The landlords feel that their social position is endangered. So, they rebel openly. They begin to form their own 'home guards', allegedly against raiders, in reality mostly against their own tenant farmers. The new guardsmen are called housecarls.  Most of them were members of the northern European warrior class. They are called Saxons.
409-420 The eastern lords discover the advantages of having their local and personal militia, called a fyrd, recruited from local Brits and led and trained by loyal Anglo-Saxons. Although the move is illegal under Roman law, they invite more and more such north-German professionals because they proved to be skilled, serious, principled, popular,  extremely loyal for bound by oath and ... cheap. Soon, peace returns and the highly effective Anglo-Saxons become a hype.
410 It's now clear that Constantine III is a failure. So western emperor Honorius is polled by the Britons about the restoration of imperial power in Britain. But there is one condition: the return of imperial legions to Britain. Honorius refuses, as he faces the Goths, declares that Britain has now to defend itself, while it has to continue to pay taxes to him.
411 Constantine III is beheaded. Britain remains excluded of imperial protection. Nothing happens. Only raids from time to time.
411-423 Honorius continues to rule as a powerless emperor while breeding chickens. Britain awaits a new emperor who can revoke Honorius' decision of excluding Britain of imperial protection. Most Britons have no doubt: the Empire will come back, as it always did before. Besides, imperial soldiers are much cheaper than the local personal guards, as they are mainly paid by the emperor.
423-424 Honorius dies. A tilting point for Britain. A letter for help (legions please!) is sent to a certain Agitius. It is thought that this person is Aetius. Valentianus III is the new but very young emperor. Young Aetius is commander in chief of the army, clearly more powerful than the emperor, but refuses. Aetius might have been seen by some as the new emperor.
425 Vortigern (= Old Welsh for chairman) with his real name: Vitalinus (Latin) or Witteling (Old English), is elected as chairman (what else?) of the London senate. He is in his early forties, smart, charming and trilingual: English (his family language), Welsh (where he grew up) and Latin. 
426 The east-British lords fear the return of the empire. They can be punished for having an illegal personal bodyguard. The emperor always was the commander of all troops within the Empire. Most lords decide to await new events in Ravenna.
427 A compromise is agreed in the senate: a local law will legalize the 'guard-system' but those local guards will now officially fall under the authority of the London senate and its chairman. It is an intermediate solution about who commands British troops. No problem: most lords with guards also have a seat in the Senate. Anglo-Saxons are now officially invited by the highest British authorities. A committee will be appointed to scrutinize the new Anglo-Saxons candidates and to direct them to their new lord.
428 Adventus Saxonum. Hengest is officially welcomed by Vortigern. He is appointed as leading officer within the selection committee. He has to work and live in Thanet (in modern Ramsgate). The Anglo-Saxons are instructed to remain within the proto-English (eastern) part of England (>Gildas). Anglo-Saxons have no problem picking up Old English but the gap with Old Welsh is great.
428-442 The housecarl system is further developed although gradually less and less North-German warriors now come over to Britain: most lords are now 'served'. A new generation of British born Anglo-Saxons gradually takes over their father's tasks. It's a period of relative peace. Many of their fathers have married local English girls, who sometimes were of the highest ranks. Opposition against the 'Saxon system' grows in the Southwest (mainly the region of Hampshire, Wiltshire, Dorset, Somerset and Devon): they want a 'legal' (read: Roman) army and the restoration of the (commercial) links with the Empire.
442-444 ? After three consecutive harvest failures, the country is in a dire state. Famine lurks, it is the Great Rebellion. A situation of total chaos breaks out, hungry tenant farmers arm themselves, begin to loot food and all is aggravated by raids. Initially the Anglo-Saxon housecarls are overwhelmed. Hengest takes the lead: he gathers an army of housecarls and crushes the rebellion in Kent. In the rest of England, law and order is quickly restored. After the Great rebellion Britain becomes officially split: the London Council versus the Southwest Alliance.  Half of the population of the Southwest Alliance still speaks Welsh, but language is not the real issue. The split is political.
445 A new gathering of the senate. Decided is to reorganize the national defence system in military provinces, redrawn according to the old tribal territories. Loyal Hengest is appointed Military Governor of Kent. Soon after, Vortigern marries his daughter. What happens in the other provinces is unclear, but probable is that powerful informal leaders are confirmed as 'governors'. Most of them are rich native proto-English landlords. Given the extreme popularity of their housecarls, they begin to name themselves 'Angle' or 'Saxon' meaning: "We shall defend our ancestral status as if we were Angles/Saxons." There is growing decentralisation all over Britain. It is now clear that the Empire will not come back.
447 Vortigern quits the Senate and retires to an ancestral estate in or near Wales. He is later besieged by troops of the southwest Alliance and dies. The political split has become a civil war.
467 Either his successor tries to restore the authority of the senate in southwest England by force or it was the lord of Wessex who had expansion ambitions. The Anglo-Saxon army is stopped at Wallop. In the east, civil power and military power become increasingly linked. It is the birth of real aristocracy.
480-490? A third generation Anglo-Saxon (probably) and captain of the mounted housecarl bands of East Anglia or the early kingdom of Linnuis defends this territory against every possible enemy: raiders from over sea, Anglo-Saxons raiders from the north, from the south and southeast, all with great success. His name is "Thor's eagle", in plain Germanic: Ar(n)-thor or Arthur. He becomes a legend much later.
500 A unnamed lord of Bath rallies the southwest Alliance or Bath is taken by Wessex forces. The southwest Alliance is called for help, they gather troops and the housecarls of Wessex experience a crushing defeat (>Gildas).
500-577 Period of peace. The expansion of Wessex to the west is halted. This ends with the battle of Dyrham (near Bath), won by Wessex.
Gildas writes his sermon around 545 AD wherein he tells us his version of the events about the Adventus Saxonum and wherein he demonstrates his profound hate towards the by then probably very popular Anglo-Saxons.