The theme of the evening was "A Tribute to Life's Coaches," and Gwynn was being honored for his work with the baseball program at his alma mater, San Diego State University. Most of the press conference centered on the pair's recent election to the National Baseball Hall of Fame, to which they'll be inducted in late July.
"As we sit here, there's no doubt about which cap we're going to wear," said Gwynn, nattily attired and seated to Ripken's left. "Cal is an Oriole. Tony is a Padre."
But the thread that brought everyone together was the devotion to growing the game through the youth of America. Ripken does that through the foundation named after his father, and Gwynn does it through his position as a Division I coach. And make no mistake about it: They both take their assignments very seriously.
"In my five years after retiring, I've had a lot to do with kids," said Ripken. "I have a whole league. The Babe Ruth League named a league after me, and it gives me a wonderful opportunity to make an impact. We've taught baseball, we've had tournaments and we've celebrated our World Series. I've had a chance to be in front of the kids.
"From my perspective it seems like the game is alive, even if the numbers are down a little bit."
Gwynn expressed admiration at Ripken's answer and said that his work has yielded a similar perspective.
"One of the reasons, to me, why being a Hall of Famer is so fun is because now I get to send that message, to talk about how great our game is," he said. "I get to do it on two fronts -- as a Hall of Famer and as a head baseball coach.
"We're at the point where we have to ask, 'How do we get more kids to want to play this game?' To me, that's part of my job."
Ripken has made this part of his mission ever since his playing career ended. He's published a book, "Playing Baseball the Ripken Way," aimed at passing on the fundamentals taught by his father, who spent more than 30 years as a player, coach and manager in the Baltimore organization. Ripken Sr. passed away in 1999, two years before his son retired.
The foundation named after him was established in 2001, and its stated purpose is to "use baseball and softball to develop character and give disadvantaged youth opportunities to succeed."
All of the Aspire Gala's proceeds go directly to the foundation, and the event has raised more than $1 million in the last two years alone.
The Baltimore Convention Center will host a memorabilia and collectibles show on Saturday and Sunday that ties into the Aspire Gala. Several members of Baltimore's 1983 World Series-winning team will be there, as will some current Orioles and Baltimore sports personalities. As Ripken and Gwynn spoke, the preparations went on outside.
"It's going to be wonderful," said Ripken, setting the weekend's itinerary. "We're having our annual gala, and we'll follow it up [on Saturday], when we have Baseball's Best. It's going to be a celebration of baseball at many different levels. A bunch of Hall of Famers are in town, and we're happy Tony came back.
"A couple of weeks ago, we enjoyed a very special moment. ... I couldn't be more proud to go in with Tony and to enjoy this journey with him. I'm glad he decided to make Baltimore a stop on his journey."
Both players are icons in their respective playing cities, but they've found a much bigger fanbase since the results of the Hall of Fame balloting were released in early January. Gwynn, in fact, said that he can't even blend into crowded airports anymore, evidenced by an anecdote from his Thursday flight to Baltimore.
"Flying in here, we had some trouble on our first plane. We had to get off and get on another one," he said. "We were in Chicago's airport, and people were just walking up to [me], shaking hands and saying, 'Congratulations.' People you don't even know. People you don't think could even recognize you when you were playing.
"It's been unbelievable. The whole process has been great."
And how appropriate is it that they'll go in together? Both Ripken and Gwynn noted the similarities in their careers and expressed the hope that there would be other pairs like them. Gwynn pointed out a small difference, though, in that Ripken got to play for his hometown team. Gwynn, on the other hand, never had to move after college.
"I grew up a Dodgers fan, went to school in San Diego and ended up getting drafted by the Padres," Gwynn said. "For me, things just kind of worked out. San Diego was a place I felt very comfortable and felt like I could establish my roots there. Luckily for me, the Padres felt the same way, and it really worked out for 20 years.
"San Diego's still home. Everything I've done in my adult life, I've done in San Diego. I'm very proud of the fact that I got a chance to start there and a chance to finish there."
Spencer Fordin is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.