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Background
It can crush you like a blind elephant."
CORDELIA
"When he wasn't being emperor he seemed hardly anyone at all. But he sure did the role well."
MILES
GENERAL
About a thousand-and-change years into the future we find the Wormhole Nexus, regions of space connected by wormholes and traversible only by interstellar jump ships. Technology has progressed as a whole, but humanity's colonization of other planets has created a situation no less politically, fiscally, or socially complicated than historical Earth. The advent of uterine replicators has erased the need for women to bear children in their own bodies, genetic engineering has caused an explosion of consequences, cryogenics can perform near-resurrections, and war has become even more convoluted than before, dominated by an arms race progressing at lightning speed. But people themselves remain largely the same, and so far, there is no one but humans present in the galaxy.
Colonization is ongoing, with each planet having its own distinct cultural background and economic role. Some have hostile environments or are undergoing active terraforming, some are little more than aggrandized space stations, and some are cultural backwaters with a strongly conservative, feudalist tone-- such as Barrayar, the defining point for Gregor's story.
BARRAYAR
HISTORY & GOVERNMENT
The original settlement of Barrayar consisted of about 50,000 people. The settlers brought with them cultural histories of Russia, France, England, and Greece, listed there in order of descending prominence. Since then, the population has grown, but by galactic standards not to very much, perhaps one or two hundred million. Geographically it is similar to Earth with a good diversity of biomes, though this was brought about by terraforming, since completed. It has two moons, a day cycle of 26.7 Earth hours, and a North and South Continent.
Primarily an agricultural colony, Barrayar has become a political empire in its own right and has since taken on a militaristic bent. For many centuries, Barrayar was entirely isolated from the rest of the galaxy due to a closed wormhole, and technology dwindled to a near medieval level. This period is referred to as the Time of Isolation. Vor lords rode horses for cavalry, maintained liege relationships with their subjects and their Emperor, and territory was split into sixty districts, each with their own Count. The comprised Council of Counts forms a tricameral legislature with the other branches being the Emperor himself and his Council of Ministers, though the relationship is more complex than that. Counts answer to the Emperor in all matters, but by majority vote and military might can overturn his decisions, leading to a history of fervent infighting. There are far fewer Ministers, who are appointed by the Emperor and do not have as much of a legislative role; they operate more as advisers and administrators.
Counts are always male, and women may not inherit, hold political positions, or join the military. (Note that I'm speaking of traditional Barrayar; Gregor changes most of these throughout his reign.) Titles are extraordinarily important, and social interactions tend toward the formal, especially with regards to Gregor due to him being the Emperor. Treason can still be punished by being drawn and quartered or through death by exposure in the public square, though that has not been enforced in years, and beheading has become the norm. The rest of the galaxy largely considers Barrayar to be detestable rural savages, at their most polite perhaps referring to them as a backwater but still decidedly negative. Barrayar plays a modest role in galactic politics; it can bring significant pressure to bear when it decides to, but that is foremost in military force and not in economic terms. Ever since the end of the Cetagandan War (read: Cetaganda's attempt to invade the weak post-Time of Isolation Barrayar, ultimately driven back by brutal and costly guerrilla efforts), Barrayar has been trying to gain more economic power.
THE VOR GAME
The basis of Barrayaran feudalism is the Vor system, and Vor can be identified by the prefix in their surname. The Vor are one link in a chain of loyalties: commoner to Vor lord to Count to Emperor to the Imperium as a whole. They are technically speaking a military caste (as Miles points out), but it is impossible to become a Count without being a Vor, and so they have maintained an unshakable grip on the power in the Empire. The Emperor himself has always been a Vor, and presently has been a member of the Vorbarra family for several generations. The name Barrayar comes from Vorbarra.
The ideal Vor is an experienced military commander, has served Barrayar violently, takes care of his district's people with generosity and economic growth, has a fierce but dutiful wife, and obeys the Emperor to his dying breath. Another duty not to be forgotten is the culturally significant obligation to have children of their blood, to inherit their titles.
Sacrifice is a long upheld tradition for the Vor: stories often tell of noble, violent deaths in the service of one of the previously mentioned ideals. Vor can also form their own liege relationships with non-Vor, taking them on as Armsmen, who are sworn to obey them exactly as they are sworn to obey the Emperor. An Armsman's oath is sacred and is sufficient legal defense against any violation of law. Each Vor house is allowed twenty Armsmen in total and no more, to prevent them forming a private army.
In practice, this described idealism doesn't always (or even ordinarily) hold. Vor are as selfish, ambitious, and downright detestable as any other person, and there is perpetual struggle within the system. Yet it is deeply culturally entrenched, and any Barrayaran subject (note they are not citizens, but subjects, a galactically important distinction) finds it inescapable. Even ex-patriots cannot totally abandon this way of thinking, whether for good or ill.
Non-Barrayarans find the whole thing relatively incomprehensible.
IMPERIAL SECURITY
The covert ops organization of Barrayar. Its name is frequently shortened to ImpSec. The Chief of Imperial Security answers directly to the Emperor himself, and they often have a close, tight knit relationship; dissent between them would be disastrous. ImpSec covers a multitude of functions, including guarding the Emperor personally, dispensing justice internally within the armed forces, gathering intelligence both domestic and abroad, and analyzing the huge swaths of data that are subsequently generated. Their symbol is an Eye of Horus and their motto is We live to serve.
They're notable here due to Gregor's continual close contact with them. The Chief of ImpSec for most of his reign and at his current time point is Simon Illyan; the main character, Miles Vorkosigan, is also in the galactic covert ops branch.
Explaining how Miles knows the Emperor personally takes us to Gregor's family history.
FAMILY HISTORY
Gregor's family history is, of course, the history of the Emperors of Barrayar. Let's take a quick jaunt through time. I promise that in the end you will see how all of this becomes relevant.
DORCA THE JUST
Somewhere to the tune of 100 years ago, the Time of Isolation ended, and around that time Dorca Vorbarra managed to unite a constantly warring chaotic mess of Counts' districts into a coherent Barrayar. Just in time to face the aforementioned First Cetagandan War. Dorca became known as Dorca the Just due to keeping the planet together enough to fight off the highly technologically advanced, ruthlessly militaristic Cetagandans. ("They don't make allies, they make conquests" would be an appropriate way to think of them.) This series truly portrays the brutality of war and mentions in some horrifying details what that time was like. Dorca keeping things together is remembered in the public memory as a lone bright spot that made survival at all possible.
MAD EMPEROR YURI
Yuri was Dorca's son and succeeded the throne upon his death, around the time Aral Vorkosigan, Miles's father, was born. (Aral becomes more significant later, so I'm tracing some of his history as well, since we're told this story through his eyes.) He was known for his immense cruelties: he personally oversaw the torture of political prisoners in ImpSec HQ, famously defenestrated the entire Privy Council himself in a fit of rage, and ordered Yuri's Massacre to kill off all those with a competing claim to the throne. Most notably, this was his half-brother Xav's descendants, including Aral Vorkosigan's family. Child Aral watched as his siblings and mother were killed. He and Padma Vorpatril were the only survivors of the massacre.
Eventually, Barrayar formed enough cohesive resistance to throw Yuri off the throne. No less bloody than their Emperor, they did so by dismembering him, forcing Aral at age twelve to make the first cut. There weren't enough pieces of Yuri for all those that wanted one-- but his scalp is still on display in the Imperial Residence's military museum.
EZAR & SERG
Ezar Vorbarra was a breath of sanity after Yuri. Barrayar has formed a well-founded paranoia about mad emperors (one Gregor shares) but Ezar was truly the force that pulled things back together. He was extraordinarily sharp, no nonsense, and clear-sighted, but he was a political man in all things and had no time for his family.
Crown Prince Serg, his son and Gregor's father, became a monster in the line of Mad Yuri. This was the time of the Ministry of Political Education-- as horrific an institution as you're probably imagining, complete with death squads-- and Serg himself came under the tutelage of a profound sadist, Ges Vorrutyer, who had once been a secret lover of Aral's. Serg brutalizes Princess Kareen, Gregor's mother, before his birth in undisclosed ways; after Gregor was born, Ezar protects them both and ensures Serg's attention is drawn elsewhere, namely to Barrayar's increasingly imperialistic aims. Gregor himself probably didn't see his father more than a handful of times before his death. He grew up unaware of his father's private reputation for torturing and raping, with a marked preference for pregnant women as his victims and men as his lovers-- seen as a perversion itself on conservative, feudalistic Barrayar-- and worse, Serg had the undisputed power and authority to escape any consequences for it.
Serg attempted assassination of his father Ezar twice before Ezar finally was willing to take action on his son's madness. He recognized that he was old, near death, and could not afford to leave Barrayar in the hands of another Yuri. He orchestrated a secret plan, and put into action a disastrous, intentionally doomed attempted invasion of Escobar, a neighboring planet. Aral was his hands on the scene, ensuring that Serg died chasing that glory. Thousands of good men died along with him. Fewer than five people know the truth of the purpose behind that war, and that Serg's death was intentional, among them Aral and Cordelia (his wife, Miles's mother).
THE VORDARIAN PRETENDERSHIP
Ezar pressed Aral into unwilling service once again upon his death, and made him Lord Regent for four year old Gregor until he came to his majority at age twenty. He trusted no one else with both the responsibility of ruling the Imperium (by this time, Barrayar had three planets under its control: Barrayar itself, Komarr which is a whole other story, and Sergyar) and the self-control to step aside and not make a puppet out of Gregor, or have him killed outright.
Shortly thereafter, however, Vidal Vordarian incited civil war in an attempt to take the throne for himself, killing the Chief of ImpSec and Gregor's personal guard left by Ezar, Negri, right in front of Gregor's eyes. With his dying efforts, Negri spirited Gregor off to Aral and Cordelia and told them what was happening.
Gregor spent most of the war hiding in the Dendarii mountains in Vorkosigan's District, shepherded around by Cordelia and then another man, Esterhazy. His secret safety was paramount to putting down the pretendership. Ultimately, they did accomplish it, but not before Kareen was murdered by Vordarian, who'd been attempting to use her as a bid for the throne himself. This left Gregor orphaned-- he lost his father, grandfather, and mother all within the same year. At that very early age, he came to understand the cost of him keeping the throne, and the even worst cost of disputes over succession.
Aral and Cordelia became very like foster parents to Gregor, responsible for raising him. Cordelia is Betan, from a completely different planet altogether, and frightfully, astonishingly progressive. She passed on many of these philosophical ideals to Gregor, as she was responsible for his education, and in this way Gregor truly was raised as a very un-Barrayaran Emperor. Aral and Cordelia's only son Miles was born shortly after the War of the Vordarian Pretendership, and Gregor was raised alongside him until he turned fourteen and was shipped off to the Imperial Service Academy.
As an important aside, Miles himself was born with physical deformities and disabilities due to a soltoxin gas assassination attempt on Aral and Cordelia during Vordarian's Pretendership.
GREGOR'S REIGN
So! Finally, we come up to date. Gregor reaches his majority at age twenty without further catastrophe, due largely to his Regent handling the Third Cetagandan War and the Komarr Revolt for him, and takes over.
Well, he takes over in name. In reality, he feels himself enclosed between Illyan and Aral, his long-time tutors not quite sure when to trust him with his own power and give him real authority. Since Gregor himself doesn't particularly want to be emperor, they have little incentive to grant him more actual power, and Gregor ends up what amounts to clinically depressed. No one aside from his very small inner social circle sees him as he really is, and even them, he feels, don't trust him, so he has difficulty trusting them.
One year into his reign, Miles at age 17 gets accused of treason (patently false) for raising a personal army in the form of a mercenary space fleet (patently true) and Gregor falls prey to the lies being fed him by a few of his advisors about it being a power grab of Aral's to maintain control of the Imperium. Miles manages to show up in his own defense and convince Gregor otherwise, and ever since Gregor has, as he puts it, been able to spot a power-hungry flatterer at a hundred meters. He's sincerely regretful to have doubted the Vorkosigans and frankly feels rather stupid about it, I suspect.
In the Vor Game, Gregor finally learns the truth about his father, Prince Serg, that's been kept from him all his life. The public hails him as a war hero tragically killed in the prime of his life during the doomed Escobaran Invasion, but when Gregor learns of the astounding depths of his depravity, he begins to question his own genetic legacy and whether he, too, won't go as insane as Yuri and Serg. It doesn't help that he gets blinding drunk that night to deal with the news, and impulsively tries to commit suicide by throwing himself off a balcony.
Instead, he gets caught on the ivy growing up the side of the wall, and discovers he can simply walk away. So walk away he does, straight onto a ship bound off-planet and gets himself dumped off without a half-mark to his name on a space station, where he gets snapped up and put in detention for loitering, then forcibly bound as a contract laborer. Miles finds him there (in detention himself), promptly freaks out, freaks out worse on hearing Gregor's admission that he'd half-heartedly tried to kill himself, and undergoes a long, convoluted, frankly Milesian plot to get him free. Involving said aforementioned mercenary fleet, which is still hanging around, if under other ownership.
Long story short, Gregor ends up prisoner of a frighteningly intelligent and ruthless mercenary commander named Cavilo. He pretends to buy into her ploy to make him fall in love with her; she opportunistically believes his half-truths about how suitable she would be as an Empress of Barrayar, that Miles's mother Cordelia paved the way to allow militaristic off-worlders to marry into the high Vor, and he remains her apparently duped captive for months. He reveals obliquely later that they had sex during this time period many times. Ultimately, though, Gregor would have in effect rescued himself, for Cavilo would've walked him all the way back across space to his own Imperial Security and delivered him straight into their hands, whereupon he could've had her arrested. And, according to him, executed if she'd gotten Miles killed.
But the Cetagandans are invading (again) thanks to Cavilo and instead Gregor is retrieved by Miles from Cavilo's clutches. He is then drawn into fulfilling his diplomatic role as Emperor and persuading the local planetary forces to help fend off the Cetagandans until the Barrayaran fleet arrives, ironically on the warship named Prince Serg. After this adventure, however, Aral and Illyan both drop comments to Miles that make it clear that Gregor has started to exert his own authority without waiting for their approval-- and both of them are vastly relieved, and proud, if terrified. Much like parents usually are.
There's another dozen books in the series after this, but aside from Gregor maturing and growing into his power, becoming comfortable with it, and meeting his wife (and turning into a correspondingly romantic sop), there's nothing of major consequence. He's usually mostly a background character, by sheer virtue of the fact that he can't leave Vorbarr Sultana without a ridiculously huge military escort. Or his own willing escape attempt.
Gregor's death without heir would throw Barrayar into war not unlike the time before Dorca, and he is very, very aware of it. There's about six different ways to interpret the lines of succession without him. After the Vor Game, he submits to being well and truly caged in his office, but now he owns increasingly more of the cage himself as time goes by, and that seems to make it sufferable for him.