As the first chief administrator of the MBTA, his job is to untangle the finances of a transit system $5.5 billion in debt and facing a $7 billion maintenance backlog. Add to that a lack of public confidence in the T after it stranded thousands of commuters during last year’s snowstorms.

But last July, Shortsleeve took a job that is no one’s idea of a political launching pad.

Given Brian Shortsleeve’s resume as a former Marine Corps officer with two Harvard degrees and a venture capitalist close to both Mitt Romney and Charlie Baker, friends always expected him to run for office one day. Maybe governor or Senate.


“When he told me he was going to do this, I was like, ‘Are you crazy?’ ” said John R. Connolly, the former Boston city councilor and mayoral candidate who has been Shortsleeve’s friend since college. “But Brian relishes a challenge. That’s really wired into him.”

The assignment has thrust Shortsleeve, a 43-year-old with no background in transportation, into a seemingly endless series of controversial decisions — to raise fares, cancel late-night service, privatize jobs, and potentially scale back or even scrap the long-awaited Green Line extension.

He has won praise for his clear-eyed focus on the agency’s budget woes and low-key, nonconfrontational style.

But union officials have staunchly opposed his efforts to outsource jobs and force the T pension board to open its records to the public, and transit advocates have criticized his emphasis on cost-cutting and efficiency over investment and expansion.

“The T has made some strides to show they’re responsible, and I think that’s really important,” said Lee Matsueda, political director of Alternatives for Community & Environment, a rider advocacy group. “At the same time, you have to lead with a vision for what the system can and should be for our region, and I think that’s where we’re really falling short.”


Shortsleeve said his goal is to balance the agency’s books for the first time in 15 years, even if that means taking on sacred cows. He said any savings will be reinvested in the system to make it run more smoothly.

“While the problems are immense and deep and structural, I reject the premise that the T can’t balance its budget,” he said in an interview in his office. “I reject the premise that that’s just the way it is. I think we can.”

Shortsleeve grew up taking the 74 bus from Belmont to Harvard Square to buy Dungeons & Dragons pieces. Now, the married father of three takes the commuter rail “pretty much every day” from his home in Wellesley to Back Bay Station.

But unlike some previous T leaders who started their careers as bus drivers, Shortsleeve does not have a long history with the agency.

He attended Belmont Hill School with two of Romney’s sons, Matt and Tagg, who remain his friends. At Harvard, he studied on an ROTC scholarship but trained at MIT and Boston University because Harvard banned the Reserve Officer Training Corps at the time.

“It has become apparent in my four years at Harvard,” Shortsleeve told the Globe in 1995, “that pursuing a career in the military is not politically correct enough for the left-wing elites running the university.”

At graduation in 1995, as friends headed to law school or Wall Street, Shortsleeve entered Marine Officer Candidates School in Quantico, Va.


“Being from Harvard and having a funny name, I took endless flak,” he said. But he bonded with another Marine who had gone to Stanford.

“We were definitely the odd men out,” Shortsleeve said. “He was the only guy who would hang out with me.”

In 1997, Shortsleeve shipped to Bosnia, where he ran a drone operation that relayed video to Army commanders maintaining peace ahead of elections. The following year, he flew surveillance drones off a Navy ship in the Persian Gulf, as part of a mission to enforce the Iraqi oil embargo.

After finishing a four-year obligation in the military, he completed a degree at Harvard Business School in 2001 and went to work at Bain & Co. A year later, Romney tapped him to be political director of his campaign for governor.

Shortsleeve had no political experience but had written a field study at Harvard Business School that calculated how many independent votes a Republican candidate would need to win in every city and town to be elected to statewide office in Massachusetts.

“I said, ‘Wow, even if this is one of the most boring things I’ve ever read, it’s also one of the best,’ ” said Ben Coes, who was handed a copy as Romney’s campaign manager.

Shortsleeve oversaw Romney’s field operation, which was one of the first to use marketing data to target voters. “Brian was the Billy Beane of that campaign,” Coes said, referring to the Oakland A’s manager whose statistical wizardry was chronicled in the book “Moneyball.”


That year, Shortsleeve also met Baker, who was a Romney campaign adviser.

After the election, Shortsleeve returned to Bain and eventually landed at General Catalyst, a Cambridge investment firm, in 2008. Three years later, Baker joined the firm as an executive-in-residence.

Shortsleeve raised money for Baker’s 2010 and 2014 runs for governor and for Romney’s 2008 and 2012 presidential campaigns. Records show he has personally donated more than $100,000 to state and federal candidates, mostly Republicans.

After Baker was elected, he asked Shortsleeve to become chief administrator of the T, a new position focused solely on the agency’s budget problems, not its day-to-day operations.

During his first nine months on the job, despite the odds and the high scrutiny, he has cut the T’s operating deficit by $138 million, or 43 percent, the result of reduced spending on overtime pay, materials, and services, and increased revenue from advertising and real estate. He has also unveiled plans to crack down on fare evasion and absenteeism.

But big problems remain.

Next month, the T will decide whether to scrap the Green Line extension, a 4.7-mile project designed to extend service into Somerville and Medford and drive economic growth in the region.

And the T must still confront its maintenance backlog, a $7 billon repair list that includes rusty signals and switches, aging vehicles, and crumbling tunnels and bridges.

“All of the fare increases in the world and all of the efficiences in the world don’t get you to solving that,” said James A. Aloisi, who was transportation secretary under Governor Deval Patrick. “So the big question is, then what? And that’s the question that’s on the table.”


The answers, Aloisi said, will have to come from Baker and from Transportation Secretary Stephanie Pollack, not from Shortsleeve, who serves as more of a chief financial officer than lead visionary. But Shortsleeve said controlling costs will let the agency focus on larger problems in the years ahead.

“I think that it’s incumbent on me and others to step into these roles and try to make it work,” he said. “When you look at how critical the T is to our economy, to our riders, we’ve got to fix it.”

Michael Levenson can be reached at mlevenson@globe.com. Follow him on Twitter @mlevenson.