In the weeks leading up to the Oct. 19 bid deadline for Amazon HQ2, Boston was widely seen as a leading contender. Now that the city’s official bid has been made public, some question if it is a case of “Boston. Yes.” or “Boston: Swing and a Miss.”

The City of Boston's Amazon HQ2 bid

Boston has chosen Suffolk Downs in East Boston as its official site selection for its Amazon HQ2 bid.

Boston’s 218-page pitch to win over Seattle’s largest employer for a second headquarters focuses much of its attention on Suffolk Downs, a soon-to-close, 161-acre horse track acquired by HYM Investment Group in May. While the site excels by offering open, developable land in Boston with easy access to an international airport, its lackluster location and questionable transportation promises have some not entirely sold on an East Boston HQ2.

“Suffolk Downs is in the flood plain. If 'The Big One' hits, it’s under water,” Nixon Peabody partner and former Boston City Council President Larry DiCara said. “Oil tanks are all around it. Oil tanks leak, and that’s just the nature of the beast.”

DiCara, like many observers, thinks one of the 26 sites Gov. Charlie Baker pitched for Massachusetts will make Amazon’s short list since the requirements outlined in the request for proposals seems tailor-made for the Bay State. Even if the horse track has potential environment concerns (which HYM founding partner and Managing Director Tom O'Brien has promised to tackle), it is seen as an easy choice by some Boston leaders because it does not requiring costly infrastructure upgrades like potential sites at South Station and Widett Circle.

The logistics of constructing upward of 8M SF of offices for a second headquarters is difficult in a space-constrained city like Boston, which some say make Suffolk Downs a no-brainer.

“In terms of the scale they’re looking for, I’m not sure we have a better site,” DiCara said.

Boston’s bid emphasizes how shovel-ready the site is and how easy it would be to advance plans because a single entity owns the property. With two on-site subway stations on the MBTA Blue Line and a five-minute drive to Boston’s Logan Airport, Suffolk Downs has its strengths. But not everyone working at Amazon HQ2 is going to live in East Boston, and it is still a tricky commute to the region’s tech hubs in Kendall Square and the Seaport.

It is possible Amazon could pick a Massachusetts bid that still includes Boston but is not coming from City Hall.

Boston's HQ2 bid cover sheet

“The Amazon bid gives us an opportunity to talk about our community values, and we think it’s a great fit,” Somerville Director of Economic Development Tom Galligani said. “It ties in with our strategy for building out our community, focused on transit and transit-oriented sites and accommodating large-scale development.”

With over 18,000 people in each of its four square miles, Somerville is the densest city in New England. It also is space-constrained and incapable of producing 100 acres as a clean development slate for the web titan.

Instead, Somerville Mayor Joseph Curtatone’s administration has pushed a regional bid that could span five cities, from Boston Properties' and Delaware North’s planned office development at Boston’s North Station, running up the Green and Orange lines through DivcoWest’s Cambridge Crossing in Cambridge and Somerville’s Assembly Row. Even places like Everett and Chelsea could see development under the Somerville bid.

“We looked at our strengths, and the emerging strengths are that connectivity,” Galligani said.

Even though the official Boston bid touts Suffolk Downs’ access to the Blue Line, others say that is not enough for a company like Amazon.

“The Somerville/Cambridge bid is centered on two rapid transit lines which, with the Green Line extension, will be connected to substantial live and play spaces in effectively four directions,” Perry Brokerage Director of Intelligence Brendan Carroll said. “Sites further afield rely on fewer lines of transit, placing a substantial load on one direction of travel as a disproportionate share of live and play is toward the city and beyond.”

The City of Boston's Amazon HQ2 bid

Boston support for the city going after Amazon is at 66%, according to a WBUR poll. Many like the idea of improvements to the city’s infrastructure and schools that would come from such a corporate titan.

“Connecting the Blue and Red Lines is a clear goal of the State and we believe an Amazon campus at Suffolk Downs will help complete that connection, which would tie East Boston and Revere directly to Cambridge, Harvard and MIT,” Boston’s bid reads.

The enthusiasm, like the bid's optimistic assertion of an hour and a half travel time to Cape Cod, is embellished. In practice, the state has shown connecting the two subway lines is far from the top of its transit to-do list. The connector would be necessary for the East Boston-Cambridge 20-minute commute cited in the bid to be remotely accurate.

The idea for a Red-Blue connector has been floated since the 1970s. The most likely path, a 1,500-foot tunnel extension from Bowdoin Station on the Blue Line down Cambridge Street to Charles/MGH Station on the Red Line, is a straightforward design. It is also a costly one. Early estimates priced the project at $750M, and the state eventually shelved the project.

If Amazon is banking on the infrastructure upgrade to improve connectivity to a potential East Boston HQ2, it could be waiting until later phases and new state leadership.

“Charlie Baker, who I’m a big fan of, has basically said we’re not going to build anything new that isn’t approved until we fix what we have,” DiCara said.