Following up his 2015, headline-making hosting gig, the Yale graduate seemed more at ease in front of the audience, and said that he's transitioned from "naive college student," joking, "Why didn't any of you warn about life after school?"
Schlossberg, who's recently been living in Tokyo, revealed that he hadn't "been in a room filled with native English speakers" in nearly a year. "Then again, we're in Boston so English-speakers may not be entirely accurate," he joked.
"I learned a lot about Japan. But the most important thing I learned was about my own country," Schlossberg said of his year as an expat. (Schlossberg's mom is currently serving as the U.S. Ambassador to Japan.) "It was something I had been told all my life but never fully grasped. I saw how people around the world see America: a beacon of opportunity, stability and strength in a world of uncertainty."
He continued, "America's historic role has been just that. America, as President Kennedy once described it 'has always been a lantern in the dark for those who love freedom but are persecuted, in misery, or in need.' "
Schlossberg said award recipient Malloy "upheld this American promise when he welcomed a family of Syrian refugees into his state after they had been turned away by another."
In return, Schlossberg – who exchanged smiles with father Edwin Schlossberg throughout the event – received high praise from Malloy, who told PEOPLE, "Jack's a great young man and in family tradition, he's a thoroughbred. And I think he's going to have a great public life if he should so choose. What he's decided now, he's decided to honor his grandfather and I think that’s a great thing. He's a wonderful young man."
During his own speech, Schlossberg chastised America's "ignorance" toward immigrants – an "enduring shame" – and highlighted Malloy's choice to go against the grain amidst the European refugee crisis.
"[Governor Malloy] took a stand against this dangerous development in our national discourse," Schlossberg said on Sunday. "He spoke honestly and intelligently to his constituents and the nation when he explained that America did not have to give up its principles to protect its people."
Schlossberg concluded, "We honor President Kennedy's legacy today by celebrating a man whose bold action embodies the principles of my grandfather's legacy."
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The Profile in Courage Award recognizes a public official "whose actions demonstrate the qualities of politically courageous leadership," according to the Kennedy Presidential Library's website.
Schlossberg has hosted the award ceremony for the past three years.
Reporting by JULIET PENNINGTON