Can John Rosenthal catch a (tax) break?

John Rosenthal doesn’t seem like he needs a handout. He lives in Carlisle and drives an Audi. But for the past year, the 57-year-old developer has been acting like he needs one, asking the City of Boston for a tax break on his $550 million Fenway Center project over the Massachusetts Turnpike.

Rosenthal will tell you he is this close to getting the first air rights development off the ground since Copley Place. The complicated project over the Pike has taken so long — more than a decade — that construction costs have ballooned by $48 million. He can’t get financing unless he can cut the pricetag, and he is all but there if the city would give him a $7.8 million break on his taxes.

Even though former mayor Tom Menino handed out plenty of goodies to developers, he wouldn’t meet with Rosenthal or even take his phone calls on the issue. The message: Go play on the turnpike.

“I am convinced that building this will be much easier than the politics over the last 10 years,” said Rosenthal.

Theories abound on the snub. Menino didn’t want Rosenthal’s good works to overshadow his own. Rosenthal is better known for saving lives than building towers; he’s behind the giant anti-gun-violence billboard over the Pike and has raised more than $20 million to help Boston’s homeless.

Or maybe it was because Rosenthal wasn’t using the right contractor — i.e., John Fish’s Suffolk Construction. Or maybe the mayor didn’t want Rosenthal to pose a threat to another favorite son, developer Steve Samuels, who has been building out the Fenway area.

Then there’s the catch-all: just because.

Menino, now Boston University professor Menino, said he didn’t mean to diss anyone. “I didn’t have time to put it together,” he said of the Fenway Center tax break. “It’s a good project. It should go forward.”

Really? No bad blood? Menino taking the high road now that he’s in higher education? “No animosity at all,” he insisted.

Rosenthal is probably the only developer happier than Don Chiofaro to see a change in administration. The do-gooder has already met with Mayor Marty Walsh about a tax break, and they plan to meet again this week.

“John is a good man. I know he has been working on this project for a long time,” said Walsh, who knows Rosenthal through his efforts on gun control and homelessness. “We are going to look at it and do what is best for the city.”

What’s best for the city is to finally break the curse on air rights projects that go nowhere. The state began leasing airspace above the Pike for development as a way to make money, but also to repair neighborhoods torn apart by the highway.

There have been missed opportunities. In the late ’90s, Millennium Partners proposed a shopping-entertainment complex in the Back Bay by the Massachusetts Avenue bridge. A decade later, Arthur Winn tried to knit together the South End and Back Bay with Columbus Center. Then Rosenthal comes up with a new vision for Kenmore Square. You can appreciate its engineering feat when you stand on the Brookline Avenue bridge, with the rumble of cars on the Pike below. Look across to Beacon Street — that’s where he plans to build a deck over the highway to connect the two blocks. There, plus on top of nearby parking lots, he plans to put up 1.3 million square feet of apartments, stores, offices, and a garage. Yeah, all of that, while we use the Pike every day.

Rosenthal came close to starting in 2009, but an abutter’s lawsuit over parking delayed everything. Rosenthal called it “extortion” and won. Last spring, Rosenthal reached an agreement with the state, which, by the way, has been generous with its concessions and infrastructure improvements such as upgrading the Yawkey commuter rail stop.

Under the Menino administration, Rosenthal was officially told the city doesn’t give incentives to projects like his that are largely residential because they’re taxed at a lower rate compared with commercial properties.

But the city finds a way to help when it wants to. Last year, Menino gave a $7.8 million tax break to two similar developments: Boston Properties/Delaware North’s project by TD Garden and Millennium Partners’s Filene’s site in Downtown Crossing. In those cases, the city helped lure supermarkets, which otherwise found downtown too expensive. If Rosenthal catches a break, he says he can put shovels in the ground by the fall and start creating 1,800 construction jobs.

It’s always hard to throw public money at private projects, but in this case, what’s good for the developer is for the greater good of the city.