These are the most common pines at our seacoasts. I'm just confirming, although the cones are pointed in weird directions which made me think of a Jack Pine.
This was in East Boston.
Japanese Black Pine
Think this one's actually Pinus nigra - the cone is a bit long for P. thunbergii. But the two are quite similar, so not easy to be certain.
Looked like Pinus nigra to me also, and for the fact that it is common in Massachusetts landscapes as planted by locals would just about assure that.
I don't know if it is a rock-solid ID separator, but I learned one of the differences between these two somewhat similar 2-needled Pine species is how the needles snap as you bend them in half. One species snaps cleanly (as if brittle) while the other bends nearly in two before breaking, if at all.
We don't have many (any?) Pinus thunbergii around landscapes I frequent in KY, so I don't have ready material to recreate which species performs which way. I'll aim to remember to try this out on Pinus nigra.