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“Justified” baddie Boyd Crowder has said it himself: “I was the man who killed men and gotten a whole bunch of men killed.”

That doesn’t make killing any easier for him, says Walton Goggins, who plays Harlan County’s criminal kingpin on the comeback trail in the FX drama.

(Spoilers ahead.)

In the Feb. 7 episode, “The Devil You Know,” Boyd crosses another line–a theme for this season–and kills a good friend, Devil (Kevin Rankin) after learning that Devil had betrayed him.

It’s a crushing blow for Boyd, Goggins said.

“I think for Boyd there is no greater sin than being disloyal,” he told me before the season began. “I think when he puts his faith in a person he puts it in wholly and he expects to be respected in that way.”

After agreeing to work with Detroit mobster Robert Quarles (Neil McDonough), Devil plans to kill Boyd and take over the business.

“Is that a note of veiled menace I detect in your voice, Devil?” Boyd asks him, cool as ever. Devil thinks he’s recruited Boyd’s brother, Johnny (David Meunier), to side with him and Quarles. Oops. Doesn’t happen.

In one of the more shocking and stronger scenes this season, Boyd shoots Devil in the chest and then stands over him, talking about loyalty and how he understands the pain Devil feels. Devil can barely speak, and only nods when Boyd asks if he wants to be put out of his misery.

It may have seemed cruel to finish Devil off, but in their world, Boyd was showing him mercy. Still, a tough day at the office.

“On that particular day Boyd was having a real hard time being the boss,” Goggins said. “He had a really hard day that day and I think it hurt him really bad. While he may not see eye to eye with Devil and he may not have a similar worldview as Devil anymore, he is still his friend. They have what I keep going back to–they have history.

“I think it breaks Boyd’s heart.”

Boyd likely will direct that heartbreak, and no doubt anger, in Quarels direction in the Feb. 14 episode, “Thick is Mud.” Also, Raylan Givens (Timothy Olyphant) will race to save Dewey Crowe (Damon Herriman) from a gang of vicious organ harvesters. Watch a preview above.