Roland is only mentioned in passing in the historical records, as the prefect of the Breton Marches, among those who fell at Roncesvals. In «The Song of Roland», however, he is the hero. Roland—that cocky, pious, stubborn, emotional knight—is a variation on the classic tragic hero: well-born, well-loved, and headed straight for disaster.
At first it looks like popularity and social status bring him nothing but good. His high rank as Charlemagne's nephew means he can throw a lot of weight around despite being a pretty young whippersnapper compared to the other knights (Ganelon's his stepdad and Charlemagne's over 200 years old). He's the first to speak up during the council about Marsile, he's immediately appointed commander of the rearguard, and Ganelon can't shut up about how many successful campaigns he's already led.
Plus, the Franks love him so much that they're happy to do whatever he says. Charlemagne values him above any knight, Oliver counts him as his best friend, and every Frank in the rearguard volunteers out of love for him. As Ganelon complains to Blancandrin:
They love him so much they will never fail him.
He gives them so many gifts of gold and silver,
Mules and war-horses, silk cloth and battle gear.
He holds sway over the Emperor himself.
He will conquer for him all the lands from here to the Orient.
In other words, Roland is popular because he's generous. He's a good noble in the feudal sense, reciprocating loyalty and military service with lavish gifts. This generosity in turn means that he's a successful commander because it's only by generating enthusiastic followers that he can conquer so many lands. Charlemagne himself is the first to admit Roland's military greatness:
"My nephew, through whom I conquered so much, is dead.
The Saxons will rebel against me,
The Hungarians, the Bulgars, and so many infidel peoples."
Without Roland to subdue it, Charlemagne's empire is as fragile as a bouquet of balloons, each one ready to pop without warning.
Despite being well-born, well-loved, and really good at war, Roland ends up dead, along with 20,000 of the best Frankish knights. How does this square with the generous, brave, fantastically successful knight? Like all tragic heroes, Roland also has a fatal flaw that leads inevitably to his downfall. But since the Song of Roland is an epic poem, not your run-of-the-mill tragic play, this fatal flaw comes with a twist.
Most of what we learn comes from Oliver and Ganelon, Roland's two biggest detractors but in different ways. Both think he has some serious personality problems. Ganelon, who hates Roland from the beginning, thinks it's arrogance. You can hear the contempt in his voice when he tells Blancandrin the story of Roland plundering in France and then cockily presenting Charlemagne with an apple:
"Here, dear lord," said Roland to his uncle.
"I present you with the crowns of all the kings."
As Ganelon points out, things other people would consider serious or tragic—like war or political power—are often just fun and games for Roland. Ganelon concludes that "his madness will surely bring him to ruin" (29.389)—the madness of arrogance, of loving war and its glory too much.
Oliver, Roland's best friend, also thinks Roland is flawed, but he thinks Roland is rash and unrea-sonable rather than arrogant. When Roland refuses to blow the oliphant out of a sense of patriotic and Christian honor, Oliver tells him he's dangerously wrong:
"I can't believe there'd be any blame in what I propose…
The armies of that foreign people are huge,
We have a mighty small company."
In most classic tragedies, the hero realizes his mistakes before he dies. The Song of Roland comes to a similar moment when Roland recognizes Ganelon's treachery and then, a little later, the enormous scale of Frankish destruction.
He dies a martyr's death at Roncesvals and is directly taken up to Paradise by saints and angels. The rest of the poem recounts how Charlemagne avenges his death.
Roland’s Timeline
Roland argues that Charles should not accept Blancandrin's offer.
Also, he volunteers Ganelon to be the envoy to King Marsile.
Dude accepts his nomination to lead the rearguard.
But he refuses to blow the oliphant and urges his men to fight for France, God, and honor.
Then he kills a lot of Saracen dudes.
Ultimately, he realizes Ganelon's treachery.
Finally, he admits the disaster and blows the oliphant to summon Charlemagne.
He then mourns the deaths of his knights.
Lastly, he retreats to a hill, tries to break his sword, and dies.
Sources:
https://www.shmoop.com/song-of-roland/roland.html
https://en.wikipedia.org/wiki/Roland
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