And before anyone says that the big dig was a success because it made traffic suck less and the waterfront got rich... Anything they did would have made traffi

And before anyone says that the big dig was a success because it made traffic suck less and the waterfront got rich... Anything they did would have made traffic suck less. With the influx of rich people back into the cities in the late 90s the waterfront was gonna get rich no matter what they did. With the benefit of hindsight it seems clear that the original 1950s/60s plans (themselves adaptation of 1940s plans) for expanding the highway and subway systems should have been followed (in no particular order so long as it all got done) and they should have tossed in a beltway line (so that literally everyone who needs to get across the city doesn't need to go downtown to do it) of some sort. They had a plan and they didn't follow it. They basically assembled 80% of the puzzle and then left it. That's why none of the major road/rail arteries in Boston link up in a sensible manner. IMO had Boston and the state not shot itself in the foot by repeatedly neutering its transit plans throughout the 20th century (killing I695, not pursuing the North/South station connector, making the silver line a bus line instead of a proper subway, the list goes on) it could have been as economically developed as the DMV area or the NYC/NJ area. Don't get me wrong, it's nice that the highway is below ground but it has its costs. Literally an entire generation of people grew up not knowing what regular infrastructure maintenance and upgrades looked like because the state was pouring all that money into a bunch of holes under Boston. It was not worth the cost. Given the choice of two ugly highways in downtown Boston bundled with any one of the planned subway developments (maybe the North/South station connector) or what we have today the choice is obvious.