On July 16, 1918, imprisoned Czar Nicholas II, his wife, and their five children were awoken in the middle of the night and led down to a basement room. Bolshevik secret police stormed in, an order of execution was read aloud, and a storm of bullets fired toward the family. Nicholas and his wife died immediately, while his children were bludgeoned, stabbed and shot again and again until they finally were killed. Imperial Russia was now dead.

That the end of the Russian Empire brought about by Russian Revolution also resulted in the former Emperor’s execution now feels like an inevitability. However, though his monarchy was overthrown, Nicholas and his family were related to many other royal families, thanks to Queen Victoria’s habit of arranging marriages for her offspring across Europe.

In the 15 months from his abdication to his death, royal relations still in power debated if and how they should grant the family asylum, with many of the Romanov descendants believing King George V of England, the czar’s cousin and grandfather of Queen Elizabeth II, could have saved them.

Would this have been a possibility, or were they doomed from the start? Here’s how the events unfolded leading up to their brutal deaths.

The web of royal marriages across the continent was so interconnected that King George V of England was first cousins to both Nicholas and his wife, Alexandra. While most of the royal relatives were fond of the warm and outgoing Nicholas, who also bore strong physical resemblance to George, Alexandra’s slightly arrogant demeanor rubbed many the wrong way, leading to growing antipathy.

After a smaller-scale revolt in 1905 forced Nicholas to cede some of his power, the couple started to withdraw from society. They began to rely on mystics and healers like the much-hated Grigori Yefimovich Rasputin to help with Alexandra’s failing health and their son Alexei’s debilitating hemophilia, which distanced them further away from the other royals and drew suspicion among many Russians.

Russia’s disastrous entry into World War I in 1914 and the ensuing defeats and hardships increased resentments toward the family, eventually erupting into the 1917 February Revolution.

Still in St. Petersburg, Nicholas’ wife and children were urged by the government to flee as the riots unfolded. Alexandra refused to leave without Nicholas, who was at the front fighting against the revolutionaries. He eventually succumbed to pressure and abdicated. The week Nicholas spent traveling back to his family was likely the last window for the family to escape Russia.

George V expressed his concern for his cousins in private letters, but he knew the situation was precarious as most Brits at the time called the former czar “Bloody Nicholas.” They also despised the German-born Alexandria just as much, as anti-German sentiment was at such a fever pitch that George V eventually changed the royal family’s name from the very German “Saxe-Coburg-Gotha” to the thoroughly British “Windsor.”

Great Britain also needed to tread lightly with the new Provisional Government in Russia; it would be a disaster for the Allies if Russia succumbed to internal pressure and withdrew from World War I.

That new Russian government, however, faced its own looming threat: what if pro-monarchist groups try to restore Nicholas to the throne? Because of this, they wanted the Romanovs out of Russia—and fast. They asked other Governments to grant the Romanovs asylum. The British agreed.

Britain regretted the offer almost immediately. The government was nervous having the Romanovs on British shores, while George V’s private secretary, Lord Stamfordham, feared an uprising against the monarchy.

The king soon urged the government to rescind the offer, leaving him open to claims that he abandoned his family for politics. “I think he’s been scapegoated for too long,” says Helen Rappaport, author of The Race to Save the Romanovs: The Truth Behind the Secret Plans to Rescue the Russian Imperial Family, adding, “[Not to] exonerate King George, not at all. He had a role he could have played more effectively…But the chips were down and they had to choose.”

Other crowned heads of Europe—mainly Spain, Denmark, Sweden, and Norway—considered ways to rescue the family, but they all feared antagonizing the new government in Russia.

The Romanovs remained under house arrest while various rumors swirled about their fate. They moved to the remote Siberian city of Tobolsk in August 1917 and, as reality set in, the family began sending hidden messages about their situation in capitivty to the outside world in hopes of reaching pro-monarchist groups.

Rappaport contends that those groups were fragmented and not aligned, asserting that “to do any kind of effective kind of rescue, you’ve got to have dedicated people, disciplined people who can keep a secret.” Lack of money and alignment among these groups were major debilitating factors.

When the Bolsheviks seized power in November 1917, even the most ardent Romanov supporters began to lose hope. While the Provisional Government seemed somewhat sympathetic to the family, the Bolsheviks wanted their heads.

After transferring to the city of Ekaterinburg, the Romanovs and their servants were imprisoned in the ominously named “House of Special Purpose.” Despite their bleak circumstance, they still were optimistic, with Alexandra writing a hopeful diary entry hours before her execution.

After the execution, only Nicholas’ death was announced, and it would be months before word of the rest of the family’s fate reached the courts of Europe.

Members of the British royal family had hoped to at least save the children. In 1919, the British sent a ship to Crimea to evacuate the remaining Romanovs. Descendants of Nicholas II’s two sisters, Olga and Alexandra, survive, as do descendants of previous czars.

In 1991, the remains of the slain family were exhumed under the newly post-Soviet Russia. DNA analysis confirmed the royal identity of the remains and they were transferred and formally interred in a special chapel in St. Petersburg, with Russian President Boris Yeltsin in attendance.