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On the Hot Seat

MassDOT real estate chief says now is a time to shine

Jeffrey Simon, head of the Massachusetts Department of Transportation’s real estate office.Pat Greenhouse/Globe Staff

Jeffrey Simon is one of the most important developers in the state. As the new head of the Massachusetts Department of Transportation’s real estate office, he controls enough prime real estate to cover nearly half the communities in the state. He spoke recently with Globe reporter Casey Ross about his strategy for managing that property and proceeding with key redevelopment projects.

This job is complicated, nettlesome, and bureaucratic. Why take it?

That’s all true. But when you look at the potential of what you can create, it’s just overwhelming. We have a huge portfolio of phenomenally good projects. We now have projects at all the major gateways into the city of Boston. We have them at both ends of the [Interstate 93] tunnel, and the Massachusetts Turnpike, so when people come into Boston by train or by car, they are going to go by one of our projects, and that is going to be their first impression of this great global city. We take that very seriously.

But it has taken a very long time to get many of these projects going, and some are still only inching along. Can you make the process move faster?


When I first talked with Transportation Secretary [Richard Davey] about this job, I said, “What’s the question we’re trying to answer?” He said to me, “Why can’t we close projects?” There are some deep-seated procedural and cultural issues that we’re starting to look at. But it’s also important to realize that these are long-term decisions. We want to get projects done quickly, but we want to do them right.

What are the different categories of real estate that MassDOT deals with?

We run 51,000 parking spaces across the state; we’re also responsible for all of the telecommunications — cell towers, fiber optic lines, and the Wi-Fi system on the commuter rail. We run all of the service plazas on the turnpike and outer 128. We have about 200 billboards. We do advertising at North Station and South Station. We do all the retail, all those Dunkin’ Donuts and flower shops, and places like that are in my area of responsibility. And that’s in addition to all of the development parcels and other pieces of real estate.


How does an organization do all of those things, and do any one of them effectively?

We need to prioritize because there aren’t enough people or hours in the day to do everything well. New things seem to pop up every day. The whole power of the integration of the transportation agencies lies in sitting down and looking at things by function, and deciding who does what well and how we avoid duplication.

What’s going to be your approach to finding and pursuing new development opportunities?

I’ve asked my staff to put together a list of sites on subway lines and commuter rail lines that I can go and look at for future transit-oriented development projects. I’m going to be on the hunt for good sites for the next weeks and months. The interest in these properties has never been higher.

Is this a unique time in terms of the amount of interest in new building projects?

Yes. There is a significant demographic change happening that I’m not sure anyone fully has a handle on. It’s the reverse of the flight to the suburbs. For the first time in recent history, you’re seeing an in-migration into cities of people with families, as well as older people. The demand for residential property is on fire, and some of that translates into retail and office demand. It’s all combining to make this a unique time to create development in places you wouldn’t have thought of before.


Does that create hope for developing some of the air-rights projects over the Massachusetts Turnpike in Boston?

Absolutely. At the Fenway Center project [next to the ballpark] you’re already seeing the new commuter rail station coming out of the ground, so that’s moving forward. At parcels 12 and 15 near the Berklee College of Music, we are negotiating a deal right now. And the Parcel 24 [housing development] has gone off to the federal highway department for approval.

Casey Ross can be reached at