Leonardo Lionheart/Affiliation

Haven Academy
Lionheart is the headmaster of the school and prioritizes its safety. However because of The Fall of Beacon, many more Grimm have surfaced in Mistral, so Lionheart had to shut his school down temporarily to send his students and staff to defend where needed.

Salem's Faction
Lionheart is a reluctant ally of Salem and her associates, acting as a mole to the Mistral Council. Lionheart is a key to her plans.

Salem
Lionheart is Salem's informant in Mistral. Lionheart is very timid in her presence and is shown to be helping Salem out of fear, as seen in "Dread in the Air". In "True Colors", he confesses to Raven Branwen that he joined Salem because he'd lost hope of her ever being defeated.

Arthur Watts
Arthur is the primary link between Lionheart and Salem. Arthur has a direct communication line between himself and Lionheart's desk. Watts also has little respect for the Professor, saying he should learn to improvise better.

Cinder Fall
Cinder is the one who reveals the full extent of Lionheart's betrayal, citing him as the reason she and her acolytes were able to enter the Vytal Festival.

Ozpin
Because of their jobs, and roles in keeping the Maidens safe, Lionheart and Ozpin are allies. However, according to Qrow, Leonardo hasn't spoken to Ozpin in some time.

In "True Colors", Lionheart confesses that he knows he has betrayed Ozpin, and strongly feels he shouldn't forgive him for what he's done to help Salem, Ozpin's sworn enemy.

In "The More the Merrier", Lionheart is confronted by Ozpin's new incarnation, Oscar Pine. During their battle, Lionheart entertains the notion of delivering Ozpin to Salem, in hopes of being "free."

Qrow Branwen
Qrow is an ally to Lionheart. However, Lionheart and Qrow disagree on many things, most recently on how to deal with the missing Spring Maiden. According to Lionheart, he couldn't arrange a team to hunt down Raven and her bandits because the Council was busy with the Grimm hordes. However this may have been a lie on Salem's behalf. Leonardo was also less than thrilled that Qrow partially filled Team RNJR up to speed on the situation.

Later, Lionheart contacts Qrow via Scroll to inform him of his "breakthrough" with the Mistral Council, knowing full well it is actually a trap set for Qrow and his allies. When the full extent of his betrayal is revealed by Raven Branwen and Cinder Fall, Qrow is livid.

When Leonardo's betrayal is revealed in "The More the Merrier" Qrow expresses his disgust for the Haven Headmaster's actions.

Raven Branwen
The two are seen together in Lionheart's office in "True Colors", after he ends his call with Qrow. Lionheart is ashamed in what he's done, but Raven counters there's no shame in wanting to survive, regardless of the cost. Though when Lionheart asks who she's trying to convince, Raven promptly excuses herself.

Vernal
The two have not interacted as of yet, but Lionheart reveals he has not seen Vernal in over ten years, after she abandoned her duties and fled Mistral. At first he's overjoyed when Qrow reveals he knows where she is, but then saddened to learn Vernal has fallen in with the Branwen Tribe.