One of the surprising things to me about the current state of the wargame hobby is the lack of attention to current contingencies.
Back in the 1970s and 1980s during the peak of the wargame hobby back then there was no shortage of games that dealt with actual contemporary military actions or the recent past. One of the early S&T games was Grunt, which depicted Vietnam combat even as fighting was still going on. Year of the Rat came out just a few months after the 1972 campaign it depicts. At least one Arab-Israeli wargame had to be redesigned because the 1973 war broke out just before publication. Test of Arms was published while some of its campaigns were still in the news. And, of course, the whole NATO vs. Warsaw Pact was an unending source of games until 1990. Even the first Gulf War prompted a batch of real-time depiction and immediate post-war titles.
In contrast, despite the fact that we're currently fighting TWO wars, there's very little to show for it. The initial march on Baghdad phase generated a little bit of action, such as Back to Iraq, but almost nothing since. Likewise the Afghanistan fighting hasn't provoked much in the way of wargame design, not even at the skirmish or tactical level. Where's the Grunt! for 2009?