Starting in the 1950s and weaving his way to the present day, Montgomery told of being a young Phillies fan who grew up rooting and went on to work for his favorite team. And then he proceeded to tell the audience how the game has changed, both on the field and in the boardrooms.
One of the most striking ways, he said, is how the players prepare in the modern-day game.
"We're much more into nutrition. It's not the cheesesteaks and the offerings of Philadelphia night in and night out. We try to do that for the visiting team," he joked. "The reality is that the whole game preparation has changed. The emphasis is on weight rooms and training facilities, batting cages and video. ... All the players now -- Chase Utley would be an excellent example on our club -- they just can't get enough of video. They just want to see who they're facing that night, what's he throwing? 'Let me see my last 10 at-bats. Let me see when I had success against him two years ago. How did he get me out last time?' or whatever. Video rooms are literally within a stone's throw from the dugout now."
Despite that salute to technology, you'll get no argument about the golden age of baseball from Montgomery. He loved the National League in the '50s and 60s despite rarely getting to see the game on television, and he said he can still rattle off lineups for several teams from that era.
But information has changed the way people perceive the game for the better, and with the increased exposure has come unprecedented popularity. Montgomery, who began in ticket sales with the Phillies in 1971, can rattle off attendance-based statistics with the best of the sabermetricians.
"I reflect to how excited we were in 1971, when we drew 1,511,000 fans that first year at Veterans Stadium," he said. "Well, that doesn't sound like such a special number today, and everybody talks about the golden period of the 50's and 60's. In 1969, our next-to-last year at Connie Mack [Stadium], we drew 519,000 people. Put that in perspective. We're doing that well at [Triple-A] Lehigh Valley."
Attendance is up across the board. Philadelphia drew 3,000,000 fans to Veterans Stadium just once, but it has a chance to do it seven times in a row at Citizens Bank Park. That's a fact that both thrills and frightens Montgomery, because it means the Phillies have to find a way to do it again.
Working at play here, said Montgomery, is a dramatic tension: Television has enhanced the appeal of the game, but is also its greatest competitor in terms of getting people to the ballpark.
At home, fans have the newest replay angles and the opportunity to hear live interviews with players and the manager, and they have their choice of refreshments waiting for them without standing on line. The appeal of the game is still there, said Montgomery, but teams need to find a sweetener.
"Everybody's time is probably the most precious commodity," he said. "You worry about the commuting time. You worry about the time they're actually in the parking lot, because what you want to do is still have the ballpark experience be No. 1. ... A good example of the way people value time: In the 1970s through the mid-1980s, we'd always schedule three or four twi-night doubleheaders.
"Two for the price of one. What could be better? That's the way I thought. You spend not just 3 1/2 hours in a ballpark. You spend seven hours. The reality is that the appeal just doesn't exist [anymore]."
Another change for the Phillies? Everything is local. Montgomery said that the team's affiliates used to be scattered between the time zones, but now they're all easy to get to from Philadelphia. That makes sense for practical reasons, he said, but also in ways that affect the team's fanbase.
"For a club that used to have teams in Helena, Montana, and Bend, Oregon, and Oklahoma City -- you name it, we were spread all over the country -- it has sure made sense to us," said Montgomery. "For two reasons: From a business standpoint, we believe that if somebody sees Cody Asche, who just joined us last night, if they saw him play for both Reading and Lehigh Valley, they may have developed some affinity for him. Perhaps they're willing to come to Citizens Bank Park and see him here. Another business reason is the cost of transporting players. We can get players like Cody Asche here in hours as opposed to flying them from one coast to the other like we had to in the past."
Montgomery, who said his family got their first television in 1950, lovingly spoke of past Philadelphia venues and noticed a strange coincidence. The Phillies played in Connie Mack Stadium for 32 1/2 seasons and Veterans Stadium for 33, but he expects Citizens Bank Park to last longer.
And who's to say it won't? Citizens Bank Park has been around since 2004, and set a record with 81 sellouts in 2010, and it can count on a boost from the proximity of the stadiums for the 76ers, Flyers and Eagles. That sports complex, said Montgomery, is a point of pride for Philadelphia.
"I think it's one of the things that makes Philadelphia sports teams unique," he said. "All four teams are playing within the city, so that the revenue we do generate ... is flowing back to our city, as opposed to being spread around," he said. "We're all there within a three- or four-block area, and I've always felt that the benefit is if one team is doing well -- if the fan comes in February to see a hockey game or a basketball game and they enjoy the experience -- hopefully they'll be back to see us come summer."
Earlier in the day, Montgomery told an anecdote that illustrated his timeless zeal for the game. The longtime executive said that in 1971, the Phillies needed a stunt to hype Opening Day at Veterans Stadium, so they planned to drop a ball out of a helicopter to a catcher waiting below.
Anticipating disaster, Montgomery decided that a dry run was in order. So there they were, two days before the stunt, and Montgomery donned a glove and learned a valuable lesson.
"A word of advice," he said. "If you do this, make sure when they drop the ball they put a rotation on it. If they drop it without rotation, it's a 600 or 700 foot knuckleball. There's no way you can catch it."