Three decades ago, a young union laborer named Marty Walsh worked for Don Chiofaro, helping to build the city's biggest office complex, International Place.
Walsh was just a kid back then, moving cinder blocks. Now as mayor, he's everyone's boss, and the fate of Chiofaro's most ambitious project since International Place is in his hands.
Recently, the Walsh administration said it's not afraid of heights on the waterfront, opening the door for Chiofaro and others to propose the tall buildings that Tom Menino loathed. The brash developer had famously clashed with our old mayor over the future of the Harbor Garage, once calling the city development process a "charade."
It was, for a few years, the best soap opera not on TV.
Today, that Don Chiofaro is unrecognizable. While he waged war with Menino, Chiofaro seems to have found peace with Walsh, reaching out on the campaign trail and again once he took office. The two have met a number of times over different issues, from job creation to Walsh's charitable initiatives.
"I am very excited about where the city is going," said Chiofaro, 68, as we sat at a table outside the Au Bon Pain in the atrium of One International Place, where he can often be found in the mornings. "It's always been a great city. But this is as an exciting time as there ever has been."
Chiofaro gives a lot of credit to the rookie mayor. "Generally people see him as a guy with an open mind and new ideas," he said.
A new mayor — and a good relationship with one — are exactly what Chiofaro needs, as he attempts to resuscitate a plan to transform the Harbor Garage, a hulking eyesore, into the next must-go-see destination on the waterfront. He and his financiers bought the garage, which sits by the aquarium, for $155 million in 2007, and have been trying to redevelop it ever since.
Chiofaro originally proposed tearing it down for a pair of skyscrapers much taller than the city allows for that area. He fought bitterly with Menino, who was concerned the towers would cast shadows on the Rose Fitzgerald Kennedy Greenway, and finally gave up two years ago. He then retreated into a self-imposed exile from the public eye.
Instead Chiofaro has been sampling other cities, studying urban waterfronts wherever he goes. He just got back from Vancouver, where he marveled at its active waterfront with restaurants, roller bladers, bike shops, ferries, and seaplanes.
These days, Chiofaro much prefers maneuvering behind the scenes, in countless meetings with residents, neighbors, and other stakeholders about his harborfront property.
The old Don focused on how high he could build to get a good return on his investment. The new Don asks the community what it wants on a prime piece of waterfront. Beaches? Swimming pool? Skating rink?
With the Walsh administration calling for more creativity on the waterfront, things seems to be finally going Chiofaro's way. Looking back, he realizes he should have behaved differently the first time around.
"My whole training in life is looking at game films," said Chiofaro, who played football at Harvard. "You look at what you did and see what worked, and what didn't work. Obviously I would have different plays."
Sometimes, the new Don is so conciliatory, you're not even sure if he wants to build anything at all. If he does nothing, he's still a rich man. Chiofaro said the 1,400-space Harbor Garage prints money — a tidy 9.5 percent return. Park there, and it won't take you long to figure out why. After a mere 80 minutes, the daily rate jumps to $36.
Chiofaro will tell you he has three options. Do nothing. Keep the garage, but wrap it with a new exterior and build on top. Or tear the whole thing down and start from scratch.
His preference is to build something new, something bold and ambitious like International Place, which, when it opened back in 1987, reshaped the city skyline.
So how high does he want to go? Chiofaro won't say. He's still working on his plans. It will take a few more months. His old proposal called for a 780-foot tower. The current limit is 200 feet, but the city is reworking that.
In talking to Harbor Garage neighbors and waterfront community leaders, there's general consensus that the garage must go, but on hardly anything else. They like the new Don, but are wise to his game pushing the public amenities: He's trying to win them over to get permission to go tall.
"At any of our ages, we don't really change," said Vivien Li, the president of the Boston Harbor Association.
Maybe so, but we should hope one thing doesn't change about Don Chiofaro. He has stuck with International Place through ups and downs, and continues to own and manage it. He keeps an office on the 46th floor, and roams the complex like he is the mayor of a city of 8,000 tenants.
Now he's working hard to become mayor of another little city, one over by the waterfront. So long as that's OK with the real mayor.