Million Dollar Homepage also comes to mind. What Kyle MacDonald has done, however, is given us another window to view Dave Littlefield's wheelings and dealings.
When MacDonald set out on his quest a little over a year ago, his goal wasn't to trade a paperclip for a house straight up. That would've been crazy, and it would've got him about as far as your typical "My girlfriend says if this page gets 1,000,000 hits I'll get laid" page that pops up on College Humor in the hotlinks twice a week. Instead, he knew his market. He had a unique angle and knew that in general the Craigslist community would be happy to get him on his way until he had something of value, so that the real dealing could begin. Once that happened, he kept an eye out for things that have more value to particular people. A good case is when he had traded down from the year's rent in Phoenix to a KISS snowglobe. To most people, a KISS snowglobe is just that, but to Corbin Bernsen, one of the world's largest snowglobe collectors, it's worth a speaking role in a movie he's directing. On each trade he either moved up, or made a move that lead to another, better move. This is in direct contrast with Dave Littlefield.
Let's just look at some of the move's DL has made in the past. It's hard to compare made deals with rumored deals or what he supposedly asked for, but there are some cases where we have a pretty good idea. First up, we can take a look at the Kris Benson deal. Littlefield's entire plan in the deal was to trade Benson for David Wright. He had no contingency plan that could be ascertained. He essentially wanted to jump from the snowmobile straight to the house with no other plan (that's why I'm doing this, Benson for Wright sounded stupid, but a house for a snowmobile sounds ludicrous). When he was made other offers, and all signs point to Ryan Howard (say, a year's rent in Phoenix) being offered. Littlefield's problem was that he already had Brad Eldred, a similar prospect at the time. Instead of taking Howard, the elusive lefty power prospect we're always after, and trading Eldred (a decent prospect at the time) for something useful, Littlefield held firm. Instead of ending up with a house or the week in Phoenix, we got Ty Wigginton (a blue paperclip, instead of the red one), and Jose Bautista (which was like trading the snowmobile to get the pen back, in terms of trade value at the time). It was a stupid strategy and Littlefield got typically burned on it. The same thing happened last year with Matt Lawton. He initially insisted on both a good prospect and a major league ready player. Again, he held firm until he ended up with Jody Gerut. That's like trading a paperclip for a bent paperclip. When the Cubs flipped Lawton to the Yankees a month later for a Class A pitcher, they at least managed to get the doorknob's equivalent to Lawton's steroid addled paperclip.
Littlefield is also unable to tell when he's holding the elusive KISS snowglobe, aka something that is far more useful to someone else than it is to him. Just a week ago the Reds traded Austin Kearns and Felipe Lopez for Gary Majewski and Royce Clatyon (with the deal being mostly for Majewski) while the Pirates sat on Roberto Hernandez and Salomon Torres. It is likely that he'll eventually get rid of Torres or Hernandez, but when he does it he'll be trading them for exactly what they are, KISS snowglobes. He failed to properly diagnose the situation; just like Corbin Bernsen collects snowglobes, Wayne Krivsky is a first year GM who's getting caught up in a Wild Card race and feels like he has to do something.
The thing that's maddening about Littlefield is that he hasn't learned after five years. He's still asking for a major league ready player and a top prospect for guys like Craig Wilson. While he's holding out, the team most likely to overpay for his guys (the Yankees) will likely move on and go after a guy like Bobby Abreu. He'll hold on until he realizes he's overplayed his hand, and when the trading deadline ends he's again going to end up holding nothing but a handful of paperclips.