At first, I had to agree with him. Then I found something very odd about the map of Massachusetts...
Take a moment to look at the southern border of the state. Aside from the beefy arm that makes up southeastern MA and the Cape, it feels like this should be a straight line. As you shoot west, however, there is a square of land that juts into what logically belongs in Connecticut. For some reason, this predominantly empty two and a half square mile block, is part of Massachusetts.
It's known as the "Southwick Jog."
Admittedly, nature abhors a straight line, and the existence of a cartographic anomaly alone isn't enough to bring interest to 17th Century colonial land grants. In fact, even though I noticed the Jog years ago, it didn't register as much more than a WTF? until it came up in a conversation with learnedax. As we mused about places like Vining Hill and Gillet's Corner (towns so small that they're not even called a towns... instead, they are "populated areas"), it was decided that we would ask the state representative of the district that contains the Jog what it was all about.
Although the official answer was a trifle disappointing, additional research uncovered stories of egregious human error, outlandish obstinance, calculated tax evasion, and bizarre royal politics. That the Jog exists actually has less to do with the presence of Lake Congamond than with the fact that the border between the two colonies was surveyed in 1642 not by professional surveyors who walked the boundary line (as was the common practice at the time), but by a couple of artists who decided to take save themselves considerable amounts to time and effort by taking nautical readings from a ship that sailed up the Connecticut River. Unfortunately, their calculations were off by a considerable margin, and the border that was determined was too far south by anywhere from four to seven miles.
Naturally, Connecticut challenged the results, but were handicapped by the small matter of not actually having a charter, essentially making the Connecticut colonists squatters who were occupying land illegally. While this oversight was corrected some twenty years later, the end result was a series of petitions to the crown from both sides of the dispute, as well as numerous legal challenges issued by border towns which stood to gain from fleeing the taxes Massachusetts was forced to levy because of King Philip's War. Town after town sued for relief under the argument that ownership of colonial territory could not be transferred without express permission of the crown and without consultation of those parties most directly involved. Feelings ran high enough that there were minor armed clashes in the border towns as this process wore on.
Ultimately the border wasn't settled until 1801, when Massachusetts offered a compromise which allowed a portion of the Jog, which had originally been given to the Commonwealth in recompense for the ceding of towns like Enfield and Woodstock to Connecticut, to be given back to Connecticut.
The more complete story is here, and it's some crazy reading.