How did Casey go from being young and idealistic (because really, at some point Casey had to have been every bit as idealistic as Chuck is) to being, well, Casey? Here's some theorizing on just that. The time-frame is not long out of spy school. First extended, non-combat mission, let's say.
"Are you ready"
The woman's hopeful smile turned John Casey's stomach. Not because she was ugly. The woman who stood before him was possessed of a sort of stoic beauty; the still considerable beauty of a woman once stunning, who had developed a deep and abiding warmth of character and personality that shown through as her physical features aged. No, though she was middle-aged, the woman had an attractiveness that could put younger women to shame.
And besides, though he was not a particularly complex man, he was far from shallow. This woman was sharp; well educated in the arts and politics and capable of holding a stimulating conversation on a variety of topics. Casey could respect competence, and though he didn't particularly value certain fields in his own life, he approached most useful subjects the way a journeyman of one field might view a related one; though he held little desire to learn, he knew art when he saw it. Though, his respect for her sharp mind was not the only reason he was pleased she was so bright.
For not the first time, the man who he buried in that Central American jungle bit back disgust. While not a particularly bloodthirsty man, he couldn't deny the rush that he got from facing down a worthy adversary. The feeling of matching yourself against an equal, wondering if you'd come out on top, only to break through and win...it was an addiction that gripped him the way few things did. But seduction...seduction...
No. Better not to dwell on such things. And while he'd never say no (he gave up far too much to ever tell them no when they made their "requests,") he still looked forward to the day when he'd finally be able to return to the battlefield.
But, now was hardly the time to be introspective. Now was the time to be charming, and attractive, and most of all, to listen. Because it wasn't his thoughts and opinions that were going to get him close enough to this woman to get what he needed, it was his ability to serve as a perfect mirror. His ability to make her loneliness subtly unbearable, until she would do anything to overcome it, even invite a virtual stranger back to the room she sometimes shared with her husband.
Because she was lonely; born to a society family that doted on her, making her a part of every party and event they held from her earliest childhood. She married her husband, a member of what she thought was a similar family from Europe, expecting that life to continue. Little did she realize, however, that the choice that she had made would render all that impossible.
First, her husband's...business made holding that sort of regular event impractical (and his finances, much barer than she had been led to believe, would not have been able to support it regardless). And, his...personal tastes...made her a poor companion for him in other, more private ways. He was of old European stock, from a generation and social class that had no problem with such private affairs in a man's life, but would not tolerate any such behavior in public. He had made it quite clear that so long as she was discreet, he had no problem with her having dalliances of her own, partially out of what he saw as kindness, but mostly owing to a conviction that she was not the sort to ever actually take him up on that offer.
But even this she would have been able to overcome with her vivaciousness and good cheer. It was his steadfast refusal to allow her the children that she so desperately wanted that ultimately put her in the state in which Casey found her. Unwilling to make the effort that it would take to give her biological children, and aghast at the possible consequences that loomed large in his own mind should anyone begin to question why such seemingly healthy people would adopt, he flatly refused to allow children into their life. Serving as a doting aunt proved a poor substitute as the years passed, and gradually loneliness became her most constant companion. A loneliness fostered by her husband. A loneliness that would prove to be his downfall. Casey would have felt slightly satisfied at the poetic justice, if it didn't involve destroying her life in the process.
But now was the time to smile. Keep the charming, boyish grin on his face. Be the young man on the rise, being entrusted with the entertainment of a business partner's wife as a test to determine just how far in the organization he would go. To bring out that charm and brilliance that was in her, to make her life seem hopelessly drab when she would return to it tomorrow. In two weeks, his superior on the team and within their cover organization would tender the offer again, and she would join him again. Her husband would accept on her behalf, only too happy to assuage his guilt at her situation.
And then...then he would finish this sordid affair. She would have him up to her room, and he would ease her pain. And then, while she rested easy, he would get a copy of the cipher that her husband kept in her safe. He expected that nobody would ever think to look in his neglected wife's possessions, and it made him sloppy. A sloppiness that they would use to learn all they needed to know to bring the men for whom her husband worked down. A sloppiness that said husband, in the desire to find someone to blame for his misfortunes, would project onto her.
Casey had no illusions about what her life would become. If she was lucky, they would manage to take out the whole organization quickly. She would be a widow, lacking any sort of means after her husband had squandered her trust fund, but she would be free. But, this was not likely. Her husband simply wasn't high enough in the organization for that to be realistic. She would be the among first targets of reprisal, as the remnants of the organization, incapable of attacking those responsible, vented their spleen at targets closer at hand. Within a month, her charm and brilliance would be gone from the world.
Somewhere, deep inside, a flash of brown eyes and a tinkling laugh caused a pang in his chest. But only for an instant.
But, he was again being distracted. The details he had memorized to seem astute about the subjects that she loved would be far from convincing if he appeared predisposed while he repeated them. Even if, at this point, he was good enough to do the job in his sleep. But, though he'd never admit it, he still felt the need to demonstrate that he was capable of doing at least as well as the agency's best, if only to himself. Casey wasn't deaf, and he wasn't a fool; he knew what the general opinion of him was. The NSA's trained pit bull; lacking subtlety and the deft touch needed to carry out this sort of assignment. That damned Montgomery had seen to that. Little did they realize that he was as adept at seduction as he was at any other aspect of his work as a spy. It wasn't hard; after all; the government hadn't spent millions figuring out how to break a person's defenses not to train their operatives in how to use what they had learned. No, it was simply easier to let the image stand.
He felt slight relief as the band struck up a waltz. Smiling, he offered a hand to the woman. She loved to dance, though she got to do it only rarely, and feigning a lack of skill would allow him to explain away why his mind was elsewhere. He would do his best to keep her on the dance floor for the rest of the night. It would remind her of happier times, and would allow him to subtly brush against her in the ways that her file suggested she enjoyed. Sometimes, he was impressed at how in-depth the information that he received could be; an ex, located by sheer happenstance in the right part of State or Treasury or elsewhere, could provide in a drunken conversation all the info that the agency needed about what direction a person's tastes ran. And this particular woman was well-covered; after all, his superior had been a serious contender for her heart, back when they were both younger. He wonders if that might be part of the reason why his superior was so adamant that they not tip their hand by attempting to get her assistance, even though the intel suggests she would accept, and it would allow them to afford her a modicum of protection.
He hopes he'll stop wondering things, some day.
They continue dancing, and he allows his hand to brush along her spine in a way that makes her shiver in spite of herself, to whisper in her ear a few times, causing her to almost melt in his arms. He realizes, with growing trepidation, that he might be asked why he didn't attempt to end the op tonight when he reports in. It's becoming increasingly obvious that he could. But now, more than ever, he needs the stability of a rigid plan to keep him going. To keep him from hating himself, once this is all over.
They manage to continue dancing through the night, and he notes with some satisfaction that she seems to recover herself as the evening draws to a close. There. Now he'll have no worries when he reports in.
He tries not to think about what the fact that he's making excuses means for his skills as a spy.
The band closes their final number, and they break apart, slowly walking to the elevator. She seems slightly surprised when he boards with her. Her surprise becomes bashful pleasure when he tells her he was always taught that it's improper not to walk a lady to her door. She blushes like a girl when he kisses her forehead, thanking her for being captivating company. He winces internally as he says it; it's too much for not closing the deal, but thankfully, she is so starved for attention that she takes to it like the desert-parched to water. He slowly walks away, counting to seven before turning around and looking at the door, knowing that she's watching him through the peephole and knowing that the most important part of being a spy is what you do when it seems nobody is watching. He manages to hold the deep sigh in until the elevator doors close, and he can be assured that the only people looking are bored security guards.
As he walks out, Casey loosens his tie. Though he has always made it a policy to never drink on a mission unless it was for the cover, he decides he simply can't hold himself to that right now. He stops, asking the concierge where the nearest liquor store is. His disappointment at being told that they're closed becomes relief as, for cost plus a nice tip, the man finds him a bottle of Johnnie Walker Black. Always more of a bourbon man, he decides that beggars can't be choosers, and takes it gratefully. Any port in a storm, after all. He takes the brown bag the concierge hands him and leaves, heading into the night.
He wonders, even as he fears, which of the women he's disappointed will greet him in his dreams tonight.
So now you know the story of why Casey likes Johnnie Walker Black. As the PSAs that raised me taught, learning is fundamental. So there's that.
To paraphrase one of the finest pieces of performance art of our era; "a bouncer in Birmingham hit me in the face with a crescent wrench five times. So if you don't review, you're not going to hurt my feelings."
(OK, I'm a total liar. I'll probably weep like a teenager. :)