Chapter 3: The Mediaeval Era (1227-1561); 3.1: Political history
The conditions for surrender were different in various parts of Estonia. In Southern Estonia the conquest was complete, with local elites either being dead or losing their position. In Northern and Western Estonia, however, the Estonian elite retained their power on a reduced scale. The Oeselian elite had the most luck, they managed to stay fairly on top for more than a hundred years.
For the general population, the conquest immediately meant two things: 1) the power hierarchy changed, with Germans now being in charge and 2) severely hiked taxes. Even though most people were baptised, the majority of Estonians did not really become proper Christians and continued to practice their pagan ways all the way until the 18th century. Individual rights were retained, including the right to bear arms.
However, the life of Estonians would get much worse over the course of the following centuries…
The mediaeval histories of Estonia and Latvia are intertwined, as back then they were considered to be a joint region. The conquered land was dedicated to Virgin Mary, and as such became known as Terra Mariana or the Land of Mary. In Estonian it is “Maarjamaa”, and that word is sometimes used as a synonym for Estonia in literary texts. Another way of referring to mediaeval Estonia-Latvia is Mediaeval or Old Livonia. It is “Old” Livonia, because later in history there was a second, smaller region which was also called Livonia. 
A map showing the political situation in Old Livonia in 1260.
The largest state in Livonia was the Livonian Order, now a sub branch of the Teutonic Order. The main capital of the Order was Riga, but their second centre was in Viljandi, Estonia. In modern day Estonia there were also the Bishopric of Dorpat and Bishopric of Ösel-Wiek (German for Saare-Lääne), as well as the Duchy of Estonia. Even though the local states acted pretty much independently, they were all part of a larger political union. As mentioned, the Livonian Order was part of the Teutonic Order, all of the local bishoprics were vassals of the Holy Roman Emperor and the Duchy of Estonia was owned by the Danish Crown. 
The Castle of Fellin (Viljandi) in its heyday.
The modern day remains of the main keep. 
The small castle of Toompea, the residence of the Danish Vicegerent and the traditional centre of power in Estonia.
The relations between the Bishoprics (or the Church states) and the Order were judicially unregulated. The Archbishop of Riga believed that the Order was actually his vassal, whilst the Order believed that it had only two masters: the Pope and God. The two sides acted as rivals and tried to actively influence and undermine each other, but neither side managed to come on top.
Mediaeval Estonia was organised according to the feudal system. Land belonged 1) directly to the Order, 2) directly to the local Bishop, 3) to the church and monasteries and 4) to the vassals of whoever was in charge. The vassals at first were from a variety of backgrounds: most likely everyone who was loyal, ready to fight and wealthy enough was able to become one, but over time the background of the vassals harmonised and hereditary noble families became the norm. The vast majority of vassals were former lesser nobles from Northern-Germany, but there were also some local, Estonian nobles among them for some time. Vassals established knighthoods in order to defend their interests against their Lord. In the Duchy of Estonia, the Harju-Viru knighthood was already established during the 13th century, in the Bishoprics they were established during the 14th century. The power of the vassals grew over time and by the 15th century it was completely customary for the local noblemen to have very big influence in local politics.
At first the land was returned to the Lord after the death of the vassal, but over time that changed as well. Over the course of the 14th-15th centuries the land the vassals owned became their birthright and the term “vassal” went out of use, it was replaced by “knight” and “noble”.
As I wrote before, the situation of the native population was not that bad immediately after the conquest, but over time it worsened. The noble/vassal class started to build manor houses all over the country and taxes were increased further. Religious repression of indigenous religions was hardened and the Church started to economically exploit the populous. In the Duchy of Estonia, the nobles became increasingly wilful and violent against Estonians. 
Around circa 1340, Estonians decided to send a delegation to the Danish King, in order to ask if he was willing to defend them against oppression. Reportedly they also said that they were willing to rather die than to live under such yoke, and if it wasn't ended, then they would complain to God about it. It is unknown what the king answered, but it is most likely that the Estonians did not like what they heard...
One the eve of the 23rd of April, 1343, one could see a light on top of a hill in Revala. It was a house on fire, but not just. It was a signal to begin an uprising.
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Mini Chapter: Saint George´s Night Uprising (1343-1345)
It was written in a contemporary source that Estonians in Revala started a coordinated attack against all Germans in an effort to “kill every single one of them, women and children included. Virgins, women, servants, nobles and commoners, young and old, everyone of German blood had to die”. The source provides very… colourful descriptions about the brutality of Estonians. However, it must be taken with a grain of salt, as most certainly it was not written by someone who was neutral in the matter, but in fact had the motivation to depict Estonians as brutal savage pagans.
However, there is some truth to it. Estonians did start to burn down manors and churches, as well as kill Germans. It is believed that about 47 of the 80 noble families in the Duchy of Estonia went extinct during the rebellion. 17 out of 21 manors in modern day Harjumaa disappeared from sources around that time. It is also possible that the rebels burnt down the Padise monastery, killing the 28 monks in the process, but that is also something not certain. Some later writers and historians believe it was just mentioned for propaganda purposes, but some believe it to be true, because the monasteries also exploited Estonians.
The rebellion was centred in the immediate region around Tallinn (Reval).
Estonians reportedly picked four peasants as their “kings” or leaders and then started to besiege Tallinn (Reval). They also sent delegates to Finland, in order to ask for help from the Swedish governor there. The governor promised to send troops. (but most likely not to help the Estonians but instead to take over the Danish territory). The wave of rebellion also spread to Läänemaa, part of the Bishopric of Ösel-Wiek, and the rebels started to besiege Haapsalu.
Germans began to flee in droves to the territory of the Order. The Danish governor sent a plea for help to the Order, as Denmark was too far. Haapsalu also asked for help. The landmeister of the Order, von Dreileben, sent a message to the rebels, asking them to meet delegates from the Order for talks at Paide (Wittenstein, a town and a stronghold of the Order). The messenger also promised to make right all the bad things the Germans had caused.
The Estonians agreed. The four kings were sent to Paide on the 4th of May. The talks have been recorded in detail, so the author of the original source was most likely in attendance. The kings agreed to be loyal subjects of the Order, as long as they did not have to serve any other masters. The landmeister said that Estonians must pay for their murder spree and ordered the kings to be locked. The Estonians secretly agreed that they would not comply and instead try to fight. It is of course unknown how the chronicle writer was able to hear the words, which were whispered discreetly. The landmeister ordered his companions to take care of the “guests” and left. The kings were cut to pieces.
The order sent a sizable force to put down the rebellion in the neighbouring territories. The promised Swedish troops did not arrive and the rebels had to face it alone. There were three major battles, Kämbla, Kanavere, and Sõjamäe. The last one was near Tallinn (Reval), the Order fought against the Estonians who had been besieging the city. The rebels lost. The landmeister also gave orders to his troops to ravage Revala and kill everyone, both young and old. Estonians had built two fortresses, where they wished to defend their women, children and property. After ransacking the land, the troops of the Order attacked those strongpoints and after fierce fighting, managed to take them.
The King of Denmark decided to sell the Duchy of Estonia to the Order after this ordeal.
A chronicle written three years later describes how Revala was an “desolate and abandoned land.”
There was a rebellion on Saaremaa too, it began in July. The Order also sent a force there, but somehow the expeditionary force returned before finishing what they were there for. At any rate, Saaremaa remained rebellious until 1345.
The condition of Estonians deteriorated rapidly following the failed rebellion. The nobles of Estonian blood were kicked out of the noble class, the peasants lost many individual rights, and the number of manors started to boom. The imposed duties to the manors also increased.
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There was a lot of movement from Germany to Estonia during the Mediaeval era. It is believed that Germans formed about 10% of the population by the late 15th century.
A specific social hierarchy formed, based on ethnicity: Estonians were lower class peasants and simple craftsmen, whereas Germans were middle class merchants, officials, magistrates, pastors etc, as well as nobles of the higher class. Moving up the class ladder was next to impossible, and even if some Estonians managed to improve their situation, they would inevitably become Germanized as they had to integrate themselves into the social strata and take over the customs, including speaking German.
Because the classes had very different rights in Old Livonia (like they did everywhere else in Mediaeval Europe), this caused a situation where Estonians were in a much less favourable position legally than Germans. Even in cities, which were like pockets of freedom when compared to the countryside, there was open discrimination. For example, if a citizen (of the city) died without heirs, their property would be handed to their closest living relative, whether living in the same city or somewhere else. But if the citizen was Estonian, and died without children, their property would be seized by the city. Other relatives were not to be considered at all. This was written down in plain text in the town law of Haapsalu (Hapsal). Germans also received less harsher punishments than Estonians.
It was written during the 16th century, that when a German, however poor and non important, walked by a manor, they were asked to step in with open arms as they were seen as brothers.
The landed nobles had the right to punish their peasants according to their vision. They were also the highest judges. Peasants gradually lost their right to move. During the 14th century, they had to pay a fine to their former lord, but by the 15th century the nobles started to demand back escaped peasants and sign treaties among each other, promising to help each other with that matter, should it arise. The sale of peasants separately from land or their families also began during the 15th century. In the 16th century, the peasants lost their right to inherit property. By the end of the Mediaeval era, Estonians had fully become serfs. Their master could sell them, punish them or even kill them. The peasants did not own anything, as they themselves were property. They had to slave away at the field of the manor, otherwise the reprisals were horrible. The masters really liked their whips.
But not all peasants were treated the same. A Swedish speaking community existed on some Estonian islands and in a region in North-West Estonia. (They migrated there around the 13th century). The majority of them were also peasants, but they were never considered as serfs and remained free throughout their existence.
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