"They threw me to the wolves, and I thought that was wrong," he said.
But now, under the new law, everyone must have health insurance. Henry qualified for state-subsidized coverage just in time.
"Do I have it right? Henry may have been on the street, essentially, uninsurable, without the Commonwealth plan?" asks CBS News correspondent Wyatt Andrews.
"Absolutely. Not only that, he might not be here anymore," says Dr. Soma Stout of the Cambridge Health Alliance.
Out of 400,000 uninsured residents last year, around 170,000 now have insurance. But the gap of 230,000 that remains includes some 130,000 young adults, most of them middle-income men who must pay for their premiums and either don't want it or can't afford it.
That's why before every Red Sox game, beside the hot dogs and hamburgers, the state is pitching health care, aiming the pitch in person and up on Fenway Park's big screen at young men.
"I have no choice. It would be like another mortgage payment for my family and I can't afford that," he said.
Health care advocate John McDonough, the executive director of Health Care For All, praises the state for a good start, but says the gap in affordability has to be filled.
"It's a tough sell because this is a group of people who've never purchased insurance on their own," he says. "It's going to be a challenge for us to make sure that policy evolves to provide an affordable option for those folks."
What's truly new about this bold experiment is that it's not voluntary. Everyone has to buy health insurance or face a penalty on their taxes. But what they already know is that "universal" health in Massachusetts won't quite be universal, for now. It's as if the game has started, but many of the fans haven't arrived.
Clarification: This story was updated on Aug. 27 to reflect that the $662 a month plan is just one of the cheapest available. The cost varies by location, age and income.