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Physical Appearance Edit
Healy is a slightly overweight, older white man with a brooding look. He often uses glasses to read fine print.
A complex figure, Healy has periods of sternness and stubbornness followed by periods of genuine care. From the beginning he is shown to be homophobic and chauvinistic. His season three showdown with fellow counselor Berdie Rogers also revealed his misogyny and possible racism.
Right at the beginning of the series, when he first meets Piper Chapman, he states to her that she should be aware of lesbians and that he hopes she is not one. Later, when Tiffany Doggett shows him Piper and Alex Vause dancing provocatively ("they lesbianing together!"), he gets so angry that he sends Piper to the SHU, claiming she would have tried to rape Alex. He once even made a suggestion to his superiors that all lesbian inmates should be sent to a separate prison from the heterosexual ones. He also posseses a book that claims women would plan to rule the world over men and enslave them, based on the idea of lesbianism.
He is shown as unsympathetic when he encountered Doggett attempting to kill Piper; he simply looked away and pretended nothing was happening even though Piper was begging for his help.
Despite this, Healy has been shown to have a good side. He secured Piper a furlough to see her dying grandmother, partly out of guilt for ignoring her when Doggett tried to kill her and after having a moment of clarity with Joe Caputo about looking after the inmates. He is shown sharing his cookie with Doggett and comforting her after she was ostricised by Leanne Taylor and Angie Rice. This in turn led to a positive friendship between him and Doggett. When Red was viciously beaten up by Yvonne Parker (Vee), Healy showed large concern for her, and after realising it was Vee, not Suzanne Warren, who had assaulted Red, Healy went to big lengths to clear Warren and see Vee pay for the crime, even going as far as fabricating details in order to convict Vee.
Red is shown to have a large amount of respect for Healy, which is for example shown when she furiously defends Healy against his mail order bride Katya, stating that "he may not be perfect but at least he's trying".
Before Litchfield Edit
Healy is revealed to possibly have a mentally ill mother. She violently throws an ashtray against the wall when he brings her food, then she immediately asks him to dance on top of a bed with her ("Mother's Day").
On one occasion as a child, Healy fearfully ran to a church after his mother became "sick" again. He sees a man that he thinks is Jesus, though he is really just a homeless person. The man vomits on Healy ("Trust No Bitch").
Arrival at Litchfield Edit
Healy began working at Litchfield many years ago. He is seen welcoming Red to prison ("Moscow Mule").
A complex figure in the prison, Healy initially seems to be on Piper's side and dispenses advice on how stay out of trouble. He expects that Chapman will serve as his informant and puppet, but she resists all such attempts. He progresses into an antagonist for Chapman, sending her to SHU on Thanksgiving for provocative dancing, and ultimately turning a blind eye as Doggett tries to kill her.
In Season Two, Healy attempts to atone for his actions in the first season and manages to secure a furlough for Piper to go and see her dying grandmother.
Healy has a Ukrainian mail-order bride named Katya, who speaks limited English. Their relationship is dysfunctional, in large part as a result of their inability to communicate, but also because Katya is disgusted by him. He previously sought relationship advice and translation from Red, but she is unwilling to help once their relationship ceased to be mutually beneficial.
In "40 OZ of Furlough", Healy is seen visiting a therapist. He then roots her. He discusses his marriage, quick temper, and dissatisfaction with his job. In subsequent scenes with his therapist, Healy gives answers and reactions akin to the inmates. It's unclear if these are his authentic reactions or if he's using the therapist's responses as a guide for his own attempts at counseling in the prison. He takes Doggett under his wing and agrees to counsel her weekly, in addition to creating a support group called "Safe Place". The group is later cancelled by Healy due to the fact that no one shows up, but he and Doggett remain close friends.
We see a flashback of him and his mother, where his mother is mentally unstable, drawing on the wall with lipstick, throwing an ashtray at young Sam then asking him to come dance with her on the bed. He also created an enemy when new counselor Berdie Rogers shows up. When Brook Soso came to him for counseling for her depression he told her that depression is "all in here" (pointing to the head). He was also wholly convinced that Soso should take antidepressants rather than get some sort of therapy for her depression, something which eventually culminates in her attempting to commit suicide with stolen allergy medication.
However, he grows closer to Red, despite him realising that she has manipulated him in order to get back onto the kitchen staff. At Lorna Morello's wedding in the visitor's room, both Healy and Red are present and share a meaningful look when Lorna and Vince exchange their vows. Red sadly tells him after the wedding that "their ships passed too late in the night", but gives him the paper bouquet she wore to the ceremony. He is later seen in his office, looking between Red's bouquet and the lunch that Katya has left for him in an attempt to bring them closer together, with an air of sad confusion.
Memorable Quotes Edit
"A couple of years ago we found two women naked from the waist down" - Moscow Mule