The fast, bloody "Godfather" takeover [...] would be [...] a formal notice to the underworld that Bulger was soon to manipulate and control. (1.2.39)
Make no mistake—Bulger isn't some sympathetic criminal who only turns to illegal activity to save his dying wife, or [insert sob story here]. He's a criminal because he loves it. He beats people up because it's fun. No wonder he rises to the rank of mob boss in record time.
"He wasn't a bully, but he was looking for trouble. You could sense him hoping someone would start something." (1.2.28)
Although Bulger wasn't a particularly cruel kid, he was certainly known to throw hands from time to time. Of course, as we'll see, adult Bulger seems to get a disturbing amount of joy from inflicting pain on other people.
It didn't matter that two prosecutors were seated across the way. Bulger leaned into Green's face, [...] "If you don't pay, I will absolutely kill you." (1.3.8)
Bulger has so much chutzpah that he'd rob a bank that was across the street from a police station. On the other hand, he might only act so tough because he knows that the FBI has his back. It's easy to be a rough rider when you have federal agents as wingmen.
Chapter 6—Part II
[J]ust five weeks after the Whitey Bulger informant file was [...] opened [...] Whitey chalked up his first murder while on FBI time. (1.6.63)
He might be utterly devoid of morals, but Whitey sure is ambitious. And punctual. Jokes aside, this is a huge early warning sign that Bulger is going to be trouble, but Connolly doesn't even skip a beat. Not a good look for an FBI agent.
They'd fallen completely off the game board [...] now criminals all, FBI agents and two gangsters looking to deflect trouble of any kind, including charges of murder. (2.9.76)
Connolly and Morris may have come in with noble intentions, but as the years pass their deal with Bulger becomes increasingly corrupt. In fact, there are multiple instance when they leak intel to Bulger that he uses to kill people. That's well beyond fudging reports or inflating your informant's credibility. That's being an accessory to murder.
There'd been a number of housekeeping murder of minor figures [...] but the growing body count brought not a single knock on Bulger's door. (2.10.9)
As time rolls on, Connolly and Morris become a well-oiled cover-up machine, successfully derailing any investigation into Bulger's violent crimes. This only makes Whitey more confident, culminating in his assassination of an Arizonan multimillionaire for screwing up a business deal.
In the aftermath Weeks found Bulger "euphoric" and unable to talk about anything else for days. (2.10.51)
The fact that Bulger enters a state of bliss after brutally murdering Brian Halloran settles the debate once and for all. Bulger doesn't just use violence—he loves it. He's a legit monster.
Morris, his wine nearby but clearly sober, said, "You can do anything you want as long as you don't clip anyone." (2.13.43)
Yeah, we're sure asking him nicely will work great, Morris. Seems to have turned out swell the past few decades. By now, Bulger has taken the driver's seat in their relationship, and he's not handing back the wheel anytime soon.
Connolly was unmoved. "But he's a good guy." Besides, he said, the dead man was "a piece of s***." (2.15.55)
Although Connolly isn't referring to Bulger here, this might help us understand how he so casually helps Bulger murder several men. Moral superiority is one heck of a drug.
James "Whitey" Bulger
Forget the "good bad guy" myth. Bulger, said Stearn, was "a serial killer." (e.27)
The revelation of Bulger's crimes causes an explosion the likes of which is rarely seen outside of a Michael Bay movie. And for good reason. Bulger has for too long hid behind his image as an anti-hero. It's time for Southie to see his true colors.