Just when it looked like air-rights projects over the Massachusetts Turnpike might be making a comeback, along comes an old-fashioned Boston spat to mess things up.

A gleaming new dorm and offices for the Boston Architectural College would rise on a deck over the Turnpike near Massachusetts Avenue and Newbury Street under plans being pushed by developer Trinity Financial.

But after making headway with elected officials and neighborhood groups, Trinity has run headlong into a major roadblock for any developer, especially one in Downtown Boston where the well-heeled typically don’t lack for top-shelf legal representation.

You see, that new dorm tower would block the views along one side of 360 Newbury, a funky, Frank Gehry-designed office high-rise retrofitted into a swank condo tower back during the bubble years.

And given the woeful history of Turnpike air-rights projects sunk by small groups of determined foes, it would be foolish just to shrug this off.

“These folks live next door – it’s their homes and their life savings,” contends Larry DiCara, a former president of the Boston City Council and the high-powered downtown lawyer representing the condo owners at 360 Newbury. “If someone was trying to put a building that was larger next to me, I would probably make a phone call or write a letter myself.”

So can a deal be worked out? Well, that all depends on who you talk to.

Point, Counterpoint

DiCara, who has seen his share of Hub development spats over the years, sees a potential compromise.

Condo owners at 360 Newbury are concerned that Trinity’s current plans would bring the dorm tower too close for comfort. Just 60 feet away, it would block sunlight and views as well – except, of course, of the young architectural students across the way in their high-rise dorm.

Such concerns are far from uncommon in a densely packed city like Boston and can be resolved with some creative design work. One basic idea, DiCara noted, is moving the tallest portion of the dorm project away from 360 Newbury.

“The standard concerns that abutters have in these situations, many times the building can be redesigned to solve many of these problems,” DiCara said.

But Trinity Project Manager Kenan Bigby has a different take on things.

The $120 million proposal, which would help bridge the ugly Turnpike canyon that for years has sliced through Downtown Boston, has been welcomed by other neighborhood groups and officials. The design starts off at the corner of Mass. Ave. and Boylston Street with an 11-story, 84-unit condo high-rise. It then drops down to six stories as it stretches out along Boylston, according to Bigby.

But before we cut to the meat of Bigby’s counter-argument, there’s a small detail worth chewing on: The tall part of Trinity’s project would face 360 Newbury, not the short end.

That said, Trinity has spent months trying to win over the high-rise’s residents, even “skinnying down the taller portions of the building,” Bigby notes.

But no matter what’s proposed, the answer has been no.

“In the end, nothing we proposed to them met with any sort of interest in coming up with a compromise,” he argued.

Whether you think Trinity is justified having a beef with its would-be abutters or not, this is simply not good news for its ambitious air-rights building plan.

A History Of Failure

Turnpike air-rights projects are especially vulnerable to even small opposition. They are big, expensive and hard to finance, and require multiple approvals from both the state’s highway bureaucracy and City Hall.

Simply put, there are reams and reams of potential red tape that a skillful group of opponents can use to wrap up some poor developer.

I could go on all day with examples, but here’s a select few:

In the late 1990s, the so-called “Fenway Action Coalition managed to torpedo a proposed Turnpike skyscraper off Mass. Ave. next door to where Trinity wants to build.

A couple years later, a few dozen South End residents managed to bog down Arthur Winn’s proposed Columbus Center air-rights project in seemingly endless rounds of community meetings. By the time Winn managed to get all his city and state permits in hand, the economy had turned and one of the biggest fiascos in Boston development history ensued.

Last but not least, developer John Rosenthal hoped his $450 million Fenway Center plan would be gearing up to build now, but instead is locked in a legal battle with the deep-pocketed real estate company that owns the building next door to his proposed site.

So where does that leave us with Trinity and its suddenly precarious-looking proposal to build an air-rights dorm over the Turnpike?

Bigby argues Trinity’s proposed dorm complex is well within city zoning for the area – it’s just 11 stories tall – and conforms with the Civic Vision, a blueprint for air-rights development.

These facts should protect Trinity from a “frivolous lawsuit,” he argues.

That’s all well and good. And it just might work in a nice, polite Midwestern city like Minneapolis.

But frankly this is the kind of battle developers don’t win in Boston. Better to turn your tower into a pretzel now to keep the neighbors happy than to spend years in court debating a plan that never gets built.

To borrow a concept from the retail industry, in the world of Boston development, the critics are always right.