"This is a sixty-year MacCutcheon," says Widmore, taking two crystal glasses and going back to his desk as he blah-blahs about an Admiral MacCutcheon, the most decorated man in the Royal Navy, who retired to the highlands to spend his remaining years making whisky, and all of it is bullshit as far as I've been able to ascertain. Widmore sets the two glasses down on his desk, and Desmond allows himself a slight smile as he thinks this is a celebration. But with this much setup, and given what we already know, I think most of us were just waiting for the guillotine blade, hey? "Admiral MacCutcheon was a great man, Hume. This was his crowning achievement," says Widmore, and pours a little whisky into just one of the glasses, and puts the cap back on the bottle. Desmond's smile falters.
Widmore holds up the glass. "This swallow is worth more than you could make in a month," says Widmore. Because the pay in your administrative department is shit? Or... oh. A stricken Desmond watches as Widmore swallows the whisky, and looks reflectively at the glass before speaking again. "To share it with you would be a waste, and a disgrace to the great man who made it. Because you, Hume, will never be a great man."
It takes Desmond a while to answer, while Widmore's eyes burn holes through him. Holy shit, Desmond. Stand up for yourself! Part of me believes Widmore's testing him. But all Desmond can do is weakly stammer out, "I know I'm not... " and Widmore cuts him off. "What you're not, is worthy of drinking my whisky. How could you ever be worthy of my daughter?" Desmond just looks around and doesn't say anything. Not, "Too bad, we love each other," not "sod off," not anything. I'm having a really hard time rooting for Desmond when he seems so paralyzed by wussiness.
Outside, though, Desmond takes out his frustration on his tie, by angrily tearing it off and throwing it down on the sidewalk. Would it have killed him to have displayed a little bit of that fire in front of Widmore? Maybe, actually -- Widmore looks kind of tough.
Even now, his anger quickly dissipates when he hears some street busker strumming away and singing "Wonderwall," and he strolls over to where people are inexplicably standing around listening to some street performer warble away a song that's been played a million times on the radio already, instead of hurrying by. There's a guy in Moose Jaw who is probably the worst street performer I've ever seen. I never actually heard him play, but that's part of what makes him so bad. He sits on a bench outside city hall, smoking, guitar at his feet. When you pass by, he croaks out, in a two-packs-a-day-for-fifty-years voice, "Ya wanna hear a song?" In my four years there, I never once saw anyone take him up on it. Now, I kind of wish I had, because what does it sound like when a guy with a voice like a car accident sings a song?