This was the worst written scene in TV history. I really turned me off the whole show. Wesley was badass, and he would have killed her just to get t done. The fact that he was there alone and leaves a gun on the table, it was so *beep* stupid I've never seen anything like it.
It's totally in-character. Like many viewers, you make the mistake of thinking it's out of character or contrived for Wesley would do something as stupid as go out and threaten Karen on his own without telling Fisk where he was going, or leave a loaded handgun where Karen could easily grab it. What you fail to realize is that while intelligence and loyalty to Fisk are two of Wesley's traits, there's another trait to his character, and that's overconfidence. Whenever he's dealing with someone throughout the season, watch how he behaves - he's always in total control, or at least, he acts like he is. Because that is who Wesley is: a guy who's in constant life and death situations, and gets by on confidence and by making reads of people and situations.
The reason Karen was able to get the drop on Wesley wasn't because he acted out of character, but because he made a HORRIBLE misread of the person and situation he was dealing with. He misread Karen the same way you and most viewers probably misread the scene. He asks her if she really thinks he'd be stupid enough to leave a loaded handgun within reach of her. Karen says "I dunno. Do you really think this is the first time I've shot someone?" and we can tell from the way her voice hardens saying that line that she is not bluffing. Wesley screwed up. He didn't take proper precautions (tie Karen up, not load the gun, not put the gun on the table within reach of her, not answer the phone, etc.) because he made a bad mistake in reading her. His own poker face in the scene is excellent, but his reading of his opponent is horrible.
There were many other times that Wesley could have met an early end, but in those scenes Wesley's reads turned out to be right. So we see him intimidate underlings, and survive. We saw him in his first appearance intimidate and threaten Farnum, threaten Farnum's daughter, and survive. If he'd made a bad read there, Farnum could have caused him all kinds of immediate problems even in a public place. But Wesley did take that precaution - he approached him in a public park. Wesley thought Karen was even weaker than Farnum. That's why he didn't even take the precaution of doing it in public.
There's also the fact that Wesley, throughout his entire career, had only ever used his strong-arm tactics on people who worked for and had every reason to be afraid of Fisk, and what Fisk might do if they refused his bidding. That typically means that his ass was already covered before he even got to speak with whoever he'd been dispatched to intimidate, so Wesley didn't feel the need to be afraid of anyone. All the calculations had been done for him before he even sat down. That causes the overconfidence that made him misjudge Karen. He tried to strongarm Karen like she's just a Fisk subordinate. Remember that in "Shadows in the Glass," when Matt chided Karen for getting herself attacked outside Mrs. Cardenas' apartment, Karen replied, "No I—I have already been hurt by those bastards! You know what? I don't care what I signed or how much money they paid me to forget, I don't. And I'm not just going to stick my head in the sand and let it happen to somebody else because I am scared! Which I am. A lot." In other words, Wesley was trying to use the fear of retaliation from Fisk to intimidate someone who wasn't afraid of what he might do. And it failed.
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