Liliana Vess is one of the most complex characters in the Multiverse. She’s a deathless Planeswalker who controls the dead; eternally youthful, but centuries old. And while she may be powerful and self-possessed, she owes a debt to the darkest demons in the Multiverse – and to one particular dragon.
The Gatewatch arc marks a transformation for Liliana: she’s no longer a lone femme fatale out for herself, and she cares deeply for those she considers her own. Her story shows the pain that comes with pursuing power, as she must choose between her ambition and her need to connect with others. A strong, fiercely independent Planeswalker, Liliana shows us a deeper interpretation of Black that balances the need for power with a desire for friendship.
Liliana’s primary motivation is to achieve personal freedom through complete power. Her desire to be herself, fully and without reservations, was something she embodied even as a young woman. Willful, beautiful and intelligent, Liliana found herself drawn to less “socially appropriate” spheres of study and society. Guided by the mysterious Raven Man, her attempt to heal her brother Josu using a potion made with necromantic energy caused him to become a raving, vengeful Lich. The horror, guilt and pain she felt upon witnessing her brother’s transformation caused her spark to ignite, sending her away from Dominaria to the dark plane of Innistrad. 
After sparking, Liliana fully embraced her talents as a necromancer. As a Pre-Mending Planeswalker, she had god-like powers that gave her the freedom to pursue anything she wished. Liliana became the person she wanted to be: strong, independent, free, and able to do whatever she wished without consequence, pain or guilt. She took pains not to connect with anyone, hoping to avoid the pain she felt when she lost Josu.
After the Mending, Liliana took a unique approach to trying to regain her powers. Unlike Nicol Bolas, who schemed, manipulated and plotted to regain power through planar conflux, Liliana chose a more direct approach: demonic contracts using her own soul as collateral. Coming to Bolas to broker the agreement, he muses:
“‘Perhaps you have already given up your soul,’ Bolas said.
The prospect did bother her, Liliana realized with some surprise. Bolas was right. Since her first encounter with the Raven Man in the Caligo Forest, when she had embraced her power and let it steer her, her life had been one moral compromise after another, an inexorable slide into darkness. What was left that separated her from the wickedest villains in the Multiverse?
Just this moment, she thought, this one instant of hesitation.” 
In that moment, Liliana realizes who she really is. While she’s been selfish, cold, and wanton with her power, Liliana is still concerned for others and what they might think of her. Her moment of hesitation opens a doorway to connecting with those around her, be they her marks, enemies or allies.
This is what sets Liliana apart from other black-aligned Planeswalkers, who are usually cast as villains in Magic lore. Unlike Bolas and Ob Nixilis, Liliana cannot help but feel for others, even when she knows she can’t afford those emotions. It’s what prevents her from playing the long game of strategy – her desire to be herself pushes her to take any short-term deals she can. This is why she accepts the demonic terms of Kothophed, Griselbrand, Razaketh and Belzenlok and, eventually, becomes the wielder of the cursed Chain Veil.
Searching For Freedom
Though her demonic contracts make her even more powerful, Liliana becomes resentful of the obligations she has to her masters. Seduced by the power of the Chain Veil, Liliana obliterates two of her demon brokers, Kothophed and Griselbrand. However, using the Veil has its drawbacks – her tattoos bleed profusely and her body weakens. Hearing the voices of the Onakke in the Veil, she tries to return the artifact to Shandalar.
Unable to break the Veil’s spell, she turns to the one person she knows who might help: the powerful telepath Jace Beleren. Jace appears to be Liliana’s one attachment after the Mending, the one vulnerability she has allowed herself after she betrayed him to be tortured by the Infinite Consortium. Even though she returned to free him, Liliana knows that her past dealings with Jace were manipulative and painful. Her guilt after betraying Jace echoes her feelings after cursing her brother, and in both situations, her pride was more important than her loved ones.
Liliana’s feelings for Jace become clearer when he visits her on Innistrad. After she fails to dissuade Jace from approaching Sorin, Jace returns half-crazed by Emrakul’s whispers. Only through the help of the Raven Man and the Chain Veil is she able to fend Jace off, and her reluctance to use her full powers saves him from certain death.
Liliana ultimately comes to the Gatewatch’s defense because she cares for Jace. While she claims her alliance with Jace is purely strategic, she secretly wants to protect him: “It wasn’t that she needed him. It was simply that she needed someone to need her.” After battling Emrakul, she joins the Gatewatch, acknowledging their collective strength and relishing the opportunity to impress Jace. However, her experiences with the Gatewatch lead her to feel new, unexpected affection for the rest of the group.
Liliana’s time with the Gatewatch is fraught with tension. She coldly assesses their strengths and weaknesses and sees herself as the shadowy ringleader of the group, slowly twisting each of the others to her purposes. Between Gideon’s tactical genius, Jace’s intelligence, Nissa’s strength and Chandra’s power, she sees her release from the Chain Veil and demon debtors as inevitable, if she plays her cards and her teammates right.
However, Liliana underestimates how much she cares about her teammates and how they perceive her. To her own surprise, she pursues non-lethal means of subduing Consulate forces on Kaladesh after Gideon reprimands her.
A single spell could drain the life from the soldiers and add their walking corpses to her retinue, and she had no doubt she could do it….Killing these soldiers would be easy—but, strangely, that had not been her plan. Perhaps Jace and—she shuddered a little—and General Meat-Shield are rubbing off on me.
Though these feelings for her allies seem strange to her, Liliana’s growing fondness for them makes sense. She perceives Gideon, Jace, Nissa and Chandra as vital to her own well-being, and she’s willing to entertain their ideas and compromise where she can. Because she cares for herself, she learns to care for them as well.
Her concern for her allies becomes apparent when they stare death and Nicol Bolas in the face. Despite defeating her third demon, Razaketh, Liliana and the rest of the Gatewatch have met their match in the Elder Dragon.
She didn’t know what made her turn to the others, but she did it anyway, the words coming before she could stop them.
“Come with me. We’ve lost. You can see that, right? We’re not going to win today…” She didn’t care that Bolas could hear her…”Please. If you stay here, you will die. This is not the way.” She hated the pleading in her voice, but she let her words stand.
Despite her pleas, the rest of the Gatewatch stays and she planeswalks away, defeated and ashamed.
Her choices always led her here. Another betrayal. Another disappointment. Another trap. It was the comfort she found in the dead. They could not be betrayed. They could not be disappointed. They could not look at her with hurt and anger in their eyes.
When Liliana meets her remaining allies on Dominaria, she tries to coax Nissa and Chandra into staying. Furious with Liliana and her manipulative ways, Nissa breaks her oath and leaves while Chandra departs to find training. Left with a wounded but stoic Gideon, Liliana brings him to her hometown in Caligo to heal. When she revisits her former family manor, she discovers that her last demon, Belzenlok, has bound the undead Josu to him to lead his Cabal forces.
This revelation horrifies and offends Liliana. She has spent centuries trying to run away from her past, but her possessive love for Josu spurs her to action. Furious, fearful and heartbroken, Liliana has no choice but to turn to Gideon.
While Gideon doesn’t seem like the type of person who would sympathize with Liliana, he understands her need to put on a facade of strength. Gideon’s own spark ignited because of his pride, and he recognizes how difficult it is for Liliana to admit weakness in front of him. While fighting Josu and his forces with Liliana, Gideon gets a deeper glimpse into her psyche:
He heard it, he heard all of it, she thought, reeling. But she set her jaw and refused to be humiliated. As he reached for her arm to steady her, she shook her head and took a step back. She forced her spine to straighten. She wouldn’t weaken. She had survived worse than this. 
Killing her beloved brother again sets off an emotional catharsis in Liliana, completely shattering her calm composure. She expects Gideon to take advantage of her weakness, but he doesn’t; he seems to understand her better than anyone else.
He knew her well enough by now to see she was genuinely worried, though her feelings were buried under layers of defensive sarcasm. She wanted to be rid of her pact, she wanted vengeance against Belzenlok, but she also didn’t want to see Gideon and Chandra hurt. 
He even defends Liliana and their plan when Jace appears on the Weatherlight and warns them of Bolas’s trap. When he reluctantly agrees to use the Blackblade, a dark magical soul-drinking sword to slay Belzenlok, Liliana is even grateful to Gideon.
He might have expected Liliana to look triumphant, or to gloat a little over his change of heart. But she just looked tired, and said, “Thank you. For this and . . .” She looked away, uncomfortable. “For . . . everything.”
Gideon smiled a little. From anyone else, it would have sounded grudging, but he knew how hard it was for Liliana to say those words. “You’re welcome.”
After defeating Belzenlok together, Gideon and Liliana prepare to meet Jace on Ravnica. However, she realizes that she cannot planeswalk – her contract has defaulted to the broker, Nicol Bolas. Unable to defy the Elder Dragon, Liliana follows him into the Blind Eternities heartsick and alone, her burgeoning relationship with Gideon brought to a standstill.
Liliana is a compelling character because her motivations are understandable, even if her actions seem amoral. One of the biggest weaknesses of Black is its lack of trust and respect for others, especially in the pursuit of power. Liliana’s initial unwillingness to be vulnerable allows her to keep her secrets secure, but it also closes her off from others. By learning to trust in others, she comes to understanding them, and they understand her, too. While most Black-aligned Planeswalkers are wary of creating bonds that might become liabilities, Liliana has realized that she can achieve more with others’ help.
It’s unclear whether Liliana will continue this trajectory of emotional catharsis as the events of Ravnica unfold. However, it is refreshing to have a character who is beginning to understand that the sweetest victories aren’t necessarily achieved alone, and that power can coexist with friendship.