Tomoyasu Chikazoku/Relationships

Re-Destro
Tomoyasu is a steadfast believer in the ideology of the Meta Liberation Army: that human beings have a right to use their Quirks whenever and however they want. Therefore, he is loyal to the Grand Commander, Re-Destro. He is shown to be able to hold a normal conversation with him and casually eat a dinner, together with him and the other Meta Liberation Army executives.

In return, Re-Destro values his colleagues. When Skeptic was using his puppets to capture Twice and kill Himiko Toga, Giran started asking questions, but Re-Destro immediately stopped him. He explained to the broker that Skeptic shouldn't be interrupted, threatening Giran.

Re-Destro knows Skeptic well, as shown when Twice overcame his trauma, he remarked that it's a rare sight to see his plans fail, which only angered Skeptic, prompting him to go directly into the battlefield. During Re-Destro’s fight with Tomura Shigaraki, Skeptic called his commander to urgently warn him about an oncoming Gigantomachia, showing concern for his leader’s safety.

After his defeat by Tomura, Re-Destro stops his soldiers from needlessly sacrificing themselves while accepting defeat and surrendering leadership of his army to Tomura, as the army were shocked by his decision.

Despite their surrender, the members are still loyal to Re-Destro and accepted his decision of forming an alliance with the League of Villains. However, they find it hard to watch his new submissive attitude towards Tomura.

When the Paranormal Liberation War has begun, Skeptic was shocked and distressed over Re-Destro's well-being, not knowing why he's the only not-League Lieutenant on Gigantomachia's back. He exclaimed that they need to ensure Re-Destro's safety, only to be turned down by Dabi.

Trumpet
Tomoyasu doesn't show any close relationship with Koku, however, they are shown to be on good terms with each other, as both of them are true believers of the Meta Liberation Army ideology. After the formation of the Paranormal Liberation Front, Trumpet calms Skeptic down, telling him that it's Re-Destro's own will to submit to Tomura and they should accept that.

Slidin' Go
When Slidin' Go berates Hawks that he's a member of higher value to the Front, Tomoyasu immediately puts him back to his place, telling him that as the Number Two Hero, Hawks is a much more reliable source of intel, while Slidin' Go is just a normal Pro Hero, being able to provide only a fraction of what Hawks can.

Tomura Shigaraki
Initially, Skeptic thought of Tomura as nothing more than an obstacle in the way of making Destro's name recognizable. However, that changed when Re-Destro acknowledged him as the Liberator and proclaimed him their new leader.

Though Skeptic respects Tomura as his Grand Commander, he still follows Re-Destro's orders.

Following the events of the Paranormal Liberation War, All For One in Tomura's body chose him as one of the few allies that Tomura should keep close to him. He then ordered him, Spinner and Dabi to look after Tomura while he recovers and perfects his body.

Twice
Tomoyasu valued Twice greatly for his Double Quirk, seeing it as something that could assist the Liberation Army's cause, as well as save Re-Destro from fatal circumstances. Because of this, Tomoyasu desired to recruit Twice into the MLA. At the same time however, Skeptic also belittled the villain for how simply he used his Quirk; having knowledge of the villain's background and how he was driven insane by his own clones killing one another, Tomoyasu created several puppets in Jin’s image in order to exploit his trauma. He then had said puppets ambush Twice, beat him up and break both of his arms for resisting capture.

This incident however forced Twice to overcome his trauma and thus overpower Tomoyasu's puppets by creating an army of his own clones. Tomoyasu, in strong denial that he had failed his objective, left to go confront Twice himself.

In return for all of this, Twice saw Skeptic as an enemy and wanted to pay him back for trying to kill Himiko. However, when the villain organizations merged, Twice no longer wanted to kill him, but still visibly enjoyed mocking the former Liberation Army leader. Angered by Twice’s attitude, Tomoyasu reminded him that it was the Liberation Army’s funds that paid for their sushi, as well as the video coverage of their battle, the League’s medical expenses and Himiko’s new coat.

When the Paranormal Liberation War started, Skeptic's initial thoughts were that Twice was betrayed by Hawks and blamed him for leaking out the information about the Front, showing that he still looked down upon Twice.

Himiko Toga
Tomoyasu appeared to support Curious' goal to publish Himiko's backstory and portray her descent into madness and villainy as a tragic case to support the MLA's cause. He laments that the footage Curious had collected during her fight with Himiko was rendered useless upon the publisher's death. Skeptic desired to have Himiko killed in revenge for her murdering Curious.

Upon locating them both, Tomoyasu had his puppets of Jin ambush Twice and a fatally injured Himiko, having them subdue the former whilst the other puppets grab Himiko and attempt to kill her by snapping her neck. Tomoyasu showed mild annoyance upon Himiko showing signs of regaining consciousness and ordered his puppets to focus on killing her.

Following Re-Destro's surrender and the Paranormal Liberation Front's creation, Skeptic and Himiko both became allies and were assigned to lead the organisation's Carmine Regiment, although neither of them seemed too happy with this arrangement, suggesting that there's still bad blood between the two.

Mr. Compress
Mr. Compress doesn't have any serious relationship with Skeptic and doesn't treat him seriously, as he calls him "long-hair", while asking him a favor. Tomoyasu, in return, seems to treat Compress in a condescending way, complaining about his lack of sophistication when it comes to modern technology.

Despite this, Mr. Compress can still have a normal conversation with him. He also appears to value Skeptic as a team member enough not to abandon him when the latter was begging for rescue. Mr. Compress then puts Skeptic's marble in Spinner's scarf, allowing him to escape.

Dabi
Dabi doesn't treat him seriously, as when he casually orders him around, not caring that he's the same rank in the organization as him. He takes him with the League onto Gigantomachia's back only because he was a key component to his plan.

When he got distracted for only a second, Dabi threatened to burn Skeptic if he wouldn't immediately return to uploading his video, to which Tomoyasu responds that the League is an unbearable bunch of people. After completing Dabi's request, Tomoyasu permitted him to grovel before him, to which the blue flame villain just ignored.

Spinner
Following the Paranormal Liberation War, Tomoyasu rallied the heteromorphs under the banner of Spinner, molding him into a symbol of true liberation, despite him claiming he's no leader. Spinner agrees, but only because All For One claims it is for the well-being of Tomura.

Hawks
Hawks finds Tomoyasu to be an obstacle, as after the League of Villains and the remnants of the Meta Liberation Army merged, it brought high chances of destruction for society.

Hawks would put up the façade of being a loyal soldier by reporting about Endeavor's activities. Skeptic planted several tracking devices on Hawks' wings, hoping to get a good image on how the heroes work, as well as to keep the No. 2 hero in check. He also finds him to be a rather useful asset, due to his high rank in the hero society.

When the Paranormal Liberation War starts, he immediately suspects that Hawks must have somehow given intel to the heroes, showing that he hadn't truly trusted him and/or had doubts concerning Hawks’ true loyalties, which were proven to be true.

All For One
While he is neither Tomura nor Re-Destro, Tomoyasu complied to following All For One commands, as long as it furthers his own agenda. When he helped All For One, telling him that so long as he can do what he wants, so will he, spreading the ideology of liberation in the new world that is to come after the Demon Lord reigns.

Curious
While they weren’t shown interacting, Tomoyasu had shown some sense of camaraderie with her, wanting to kill Himiko in order to avenge her death.

Giran
Skeptic finds him annoying, as when he asked about some 'footage' Tomoyasu mentioned, he grabbed his face and started mocking him for not asking in full sentence, asking whether he's like a parrot that repeats after other people.