Jason Bay, a lifelong hockey fan who grew up in Trail, British Columbia, couldn't believe his misfortune.
"He had come through the clubhouse before the game, and I missed him," said Bay, "and I was talking to someone who brought him in and I said, 'You brought him, and he didn't even come to say hi?' So they were trying to set something up."
The setup, it turns out, was executed perfectly. Orr spent the bottom of the sixth inning inside the fabled Green Monster, even peering through the scoreboard window between pitches. So when Bay, Boston's left fielder, came out to play defense in the top of the seventh, Orr stood on the warning track in front of the Monster and shook hands with Bay.
"Someone had given me a little heads up that he was out there," said Bay. "I was under the impression that he was going to heckle me or something for an inning. But he just waved me over and said, 'Nice to meet you.' I knew he was around. I didn't know if I'd see him after the game. Little did I know it would be during the game. It was a thrill, nonetheless."
All this on a night the Red Sox not only won, but extended their record-setting sellout streak at Fenway Park to 500 games.
"It was one of those things, he was huge for hockey in Boston," said Bay. "But it's not just Boston. He was a huge Canadian guy. There's only a few guys like that in that sport that I think you really identify with, and he's definitely one of them."
Bay only wishes his father, Dave, a certified sports nut, could have been there for the meet and greet.
"Big win, but also a big deal," said Bay. "I got to meet Bobby Orr."
Boston's left fielder is already looking forward to the next encounter with the former Boston Bruins megastar.
"Hopefully, I run into him again and talk a little bit longer," said Bay.
Ian Browne is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.