It's actually an item override that appears to be the issue, as it happens when mafia finds a new item and generates its 4 files based on that. It's possible that a monster may cause it, but when I fight unknown monsters, it's usually tied into new items as well.
1) Windows 7 64-bit, using various new versions of Java. Currently 1.6.0.23, has also happened on .19, .21, and .22. Missed the .20 compiler, if memory serves.
2) My 'standard' launch is my KoL.bat file, which runs KoLMafiaUpdate.exe, found in the update threads, and which downloads the latest daily build and copies it to KoLmafia-latest. It's a good way to know I'm up to date. I did try both launching it through double-clicking on the jar and by manually launching java -jar KoLmafia-latest.jar and both returned the same error. However, the java one did present the following crash-text:
Exception in thread "main" java.lang.ExceptionInInitializerError
at net.sourceforge.kolmafia.AdventureResult.<init>(AdventureResult.java:213)
at net.sourceforge.kolmafia.objectpool.ItemPool.get(ItemPool.java:1213)
at net.sourceforge.kolmafia.RequestEditorKit.<clinit>(RequestEditorKit.java:1938)
at java.lang.Class.forName0(Native Method)
at java.lang.Class.forName(Unknown Source)
at net.sourceforge.kolmafia.KoLmafia.class$(KoLmafia.java:149)
at net.sourceforge.kolmafia.KoLmafia.<clinit>(KoLmafia.java:149)
Caused by: java.lang.ArrayIndexOutOfBoundsException: -64
at java.util.ArrayList.set(Unknown Source)
at net.sourceforge.kolmafia.utilities.IntegerArray.set(IntegerArray.java:59)
at net.sourceforge.kolmafia.persistence.ItemDatabase.readTradeItems(ItemDatabase.java:357)
at net.sourceforge.kolmafia.persistence.ItemDatabase.reset(ItemDatabase.java:276)
at net.sourceforge.kolmafia.persistence.ItemDatabase.<clinit>(ItemDatabase.java:255)
... 7 more
Could not find the main class: net.sourceforge.kolmafia.KoLmafia. Program will exit.
Addendum: The item I'd marked as not existing was the old sweatpants, since every character is guaranteed to have them unless you scrap them somehow. I marked as non-existing by commenting (#) out the line for the pants in equipment, itemdescs, and tradeitems. I then commenced recompiling, copying the file over my launch file, starting mafia, logging in (generating override file), completely exiting mafia, and trying to relaunch (at which point the error above appeared). Override files should be attached now.