Night Shade

Night Shade was a secondary antagonist of the Soldier's Memoirs saga, and the primary antagonist of Skyfall. He was a deranged male unicorn bent on assassinating Princess Celestia in redemption for her strategic failure during the Frozen North Offensive.

The Frozen North Offensive
Night Shade was one of the ponies selected to take part in the Frozen North Offensive to drive the dragons away from Equestrian settlements in the Frozen North. Although he sustained no injuries himself, Night Shade witnessed the deaths of every single one of his friends and comrades, many succumbing to the elements while they waited for reinforcements to arrive and rescue them. Help never came, however, and Night Shade was forced to seek help with Nightingale, the only other remaining survivor. Nightingale eventually perished as well, leaving Night Shade bitter and furious with Princess Celestia for sending them on a suicide mission and abandoning them to their deaths. He made his way back to Canterlot only to find the princess had covered up the battle entirely. Night Shade vowed to have vengeance on Celestia and make her pay for throwing the lives of his friends away so callously.

The Double-Edged Sword
During his years of hiding, Night Shade sought out an underground group of ponies that resented the alicorn as much as he did. While initially a nonviolent group, Night Shade worked his way into their ranks and spread his hate through their minds, poisoning them one by one with his charm and words until they all regarded his word as law. Following the Second Griffon-Pony War, dissent towards Celestia grew in their ranks, and Night Shade saw the perfect opportunity to strike. He began sending threatening messages to the Royal Family in secret, hoping to lure them out into the open for him to assassinate them. However, when they failed to take the bait, Night Shade took more direct approaches. He sent assassins into Canterlot Castle to find the princess. The assassin, however, was found and killed. In the following days, Night Shade decided to take matters into his own hooves. He permitted himself to be captured by Fleethoof so he could infiltrate the castle, then sent Skyfall Unit on a wild chase while he was freed by his fellow Sword members. After stealing weapons and kegs of gunpowder from the Royal Guard armory, he made an attempt on the princesses' lives, but was stopped by Shining Armor and Fleethoof again. He was able to escape, however, and ordered several of his remaining members to go to Saddle Arabia after Princess Cadance, hoping to use her as leverage against Celestia.

While he waited for his ponies to return with Cadance, Night Shade and the rest of the Sword continued to harass the Royal Guard by launching guerrilla attacks on them from the sewers. When Night Shade received word that his plans to capture Cadance had been foiled, he resorted to his final strategy. He placed the kegs of gunpowder and explosives beneath Canterlot Grand Station and set up an ambush in the station lobby. When Princess Celestia, Princess Luna, and Shining Armor came to welcome Cadance back, Night Shade struck, capturing the entire lobby hostage. Skyfall Unit arrived a few minutes after to quell the situation, but were stuck in a tense standoff. Fleethoof continued to try to reason with Night Shade. Night Shade only offered cryptic remarks back to the pegasus, alluding to Nightingale all the while. Before he could detonate the explosives, however, he was killed by a single gunshot to the head from Sharp Shot.