Although some might use 'The Five Boroughs' to refer to New York City or even Cincinnati, this term really refers to the part of the old kingdom of Mercia that fell to the Viking invasions of the late ninth century, and recognized as part of the Danelaw by Alfred the Great of Wessex.  The area under the control of the Five Boroughs is roughly equivalent to today's East Midlands, bounded by the Humber and Trent, Watling Street, and the fenlands around The Wash.  I'm not sure how Cheshire fits into this, if at all.

The Danes raided into this area in the eighth and early ninth centuries, but even as late as 868, settlement was primarily Anglo-Saxon.  The campaign of Ivarr the Boneless changed all of that.  The 870 death of East Anglian king St. Edmund  at Ivar's hands gave the Northmen free rein over the area. After Alfred's treaty establishing the Danelaw, they gave up raiding for settlement. They fortified four towns:

and built a fifth, Derby.

Each town and the area around it was under the control of a different Viking band.  The bands' overlords formed a loose confederation under the nominal overlordship of the kings of Jorvik to the north.

The Five Boroughs became the first step in Wessex's eventual conquest of the Danelaw.  Edward the Elder began his campaign into East Anglia and the Five Boroughs 914.   Derby was the first to fall, in 917.  The same year, Edward's army defeated the East Anglian army at the Battle of Tempsford, killing king Guthrum II (the mopping up of East Anglia took another year).  Leicester was taken early the following year, causing the other three boroughs to surrender.  By 920, Edward was in control of everything south of the Humber, and even had the fealty of King Ragnald of Jorvik, as well as everyone else in Britain.

Wessex's control of the Danelaw was always shaky at best. In 939, just after the death of Aethelstan, Olaf Guthfrithson, the king of Dublin, wrested the Five Boroughs and much of the old kingdom of Jorvik away from Wessex.  Aethelstan's son Edmund I recaptured the Five Boroughs in 942. A revolt in 957 saw the Five Boroughs (and the rest of Britain north of the Thames) shift their allegiance1 from Edwy the Fair to his brother Edgar.

The Five Boroughs were among the first territories to fall to Sweyn Forkbeard and his son Canute in 1013, and were the prize given to Edmund II Ironside after switching his allegiance from his father Aethelred to Sweyn.

1One suspects that one faction of earls and abbots had eighteen-year-old Eadwig as their figurehead, and another (led by Eadwig's enemy, Abbot Dunstan) fronted themselves with thirteen-year-old Edgar.

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