Heart of New England, birthplace of the Revolution, home of Otis, Adams, and Hancock, Massachusetts was a cornerstone of early America. I'm sure their flag reflects the rich history of this commonwealth, so lets take a look.
The flag of Massachusetts is white. The figure in the center of the purple shield represents an Algonquian Native American, the severed arm atop the crest signifies the commitment to fight for liberty, and there is a lovely Latin inscription on the ribbon surrounding the shield.
This flag is really disappointing. Although it's imagery recalls the rich and defiant history of Massachusetts, one needs to have a detailed description handy to make much sense of it. This is not the sort of image that one could put on a T-shirt and not need to also put the state name (Colorado is a great example of this, as is Texas). It might as well be stitched to a blazer for a preparatory school.
Another area of disappointment comes from the fact that Massachusetts has a rich flag history from which they could draw. This is one version of the Bunker Hill flag (there is quite a bit of controversy here, as some records indicate no flag was flown by the Americans at that battle, while others give varying colors and descriptions):
This one is nice and far cleaner than the current one, but wouldn't make much sense for a place so proud of its ability to break away from the English crown. The red cross in the canton is the cross of St. George, patron saint of England and namesake saint of King George III, who by the end of the Revolution wasn't very popular in Massachusetts for some reason. On a more personal level, the blue used is very similar to that used in a large number of other state flags, so let's steer away from that. Thus I submit another historical flag, the flag of New England from the same period:
This flag is nice and evocative. There is a simplicity in its design and the largely red field would really stand out among its state flag brethren. (I tried moving the tree into the center and removing the white altogether, but it looked too much like I was trying to entice customers to a Christmas sale). The pine tree has been a symbol of New England for centuries, and I think Massachusetts has just enough ego to think they could get away with claiming this regional flag as their own. In defense of that statement though, it's not like anyone else is using it.
My only improvement would be to par down the tree a bit and remove the darker green lines:
Not a big change, but I think, an improvement nonetheless, and head and shoulders above the one they have now.