Bennett's debut came on Sept. 24, 1995, against the Reds at Veterans Stadium. He struck out in what turned out to be his only at-bat of the season.
"First and foremost, what sticks out is the first day being called up. There's a story I like to tell about some colorful language from some folks in the stands. It makes me laugh," he said, when asked about his most vivid memories of playing in red pinstripes.
It was also in Philadelphia that Bennett grew into the player who was able to enjoy an extended career as a back-up catcher.
"[Manager Jim] Fregosi was great to me," he said. "I didn't play a whole lot, obviously, but he always communicated with me, and afterwards we'd sit down and have a refreshment in the clubhouse and just talk baseball. That's a very fond memory I have early on, and it helped me tremendously. One, just to feel comfortable there, but to learn the game and become a better player."
Now 42, Bennett has stayed busy since retiring in 2008. Before that season started he became a partner in a baseball facility called Slammers, just north of Chicago. In his words, he's "working with young athletes, trying to pass along a little bit of what baseball taught me and what baseball gave me."
Bennett also works with Smith and Nephew Orthopaedics in Chicago for joint reconstruction and WRS for post-operative healing and pain management -- an opportunity that directly resulted from his time with the organization.
"I got turned on to that by a former teammate in the Phillies Minor League system, Craig Holman," Bennett said. "We were roommates at Triple-A. He started in the business in 2001, 2002. He gave me a call and basically said, 'I hope you hit 35 home runs this year and drive in 130 runs and sign a contract where you never have to work again. But if that doesn't happen, I have a job I think you'll enjoy."
Bennett has been there since March, 2010.
He's also partnered with a friend in a real estate company, focusing on acquiring rental properties. He occasionally goes to St. Louis to do pre and postgame coverage of Cardinals games for FOX Sports Midwest.
Bennett and his wife Ruby have three children -- 13-year-old Garrison, 11-year-old Gavin and 9-year-old Julia. The boys play baseball, among other sports, and he coaches both their teams. "I've got a few irons in the fire, that's for sure," he said with a laugh.
When baseball instituted new rules regarding home-plate collisions this year, Giants manager Bruce Bochy was one of those pushing hard for the change. And Bochy said it wasn't because his All-Star catcher Buster Posey had been seriously injured in 2011. It was because of a play eight years earlier involving Bennett at Dodger Stadium when Bochy was managing the Padres.
"I remember that play up until impact," Bennett said. "Brian Jordan was the runner. I think there was a man on third, and we hit him with a pitch with one out, so obviously he wasn't exactly enthused. I guess there's two ways to look at that. Either one got away or we're going to pitch him in and if we hit him, we've set up the double play. I think he took it the second way."
Fred McGriff hit a ball into the corner. Jordan beat the throw by a split second and flattened Bennett, knocking him some 15 feet off the plate. Still, Bennett has mixed emotions about MLB's attempt to eliminate those situations.
"I didn't have a problem with it," he said. "I thought it was a good, clean hard play. I was trying to take the plate away and he wanted the plate. I didn't think he went out of his way to hit me. I don't think I gave him much of the plate to slide into.
"I just think [the enforcement has] been a little inconsistent. Sometimes you have the exact same play, the exact same positioning, and one time it goes one way and one time it goes the other. I like the thought. It takes away someone getting run into or hurt for no reason, runner or catcher. I like that. But on a bang-bang play where there's a lot of action around the plate, I just think it's very difficult to police."
Bennett was with the Phillies organization from the day he signed until he was traded to the Mets for Todd Pratt on July 23, 2001 -- except for the 1997 season, which he spent at Triple-A Pawtucket in the Red Sox system. That, too, became a lesson.
"In '96 I was taken off [the big league roster for the second time] and basically had my feelings hurt," he explained. "They said they wanted me back, but I just took it personally and decided to go elsewhere. I went to Boston for a year, and it was a great learning experience. I didn't necessarily have a very good year. And as soon as the season ended the Phillies called back and said, 'Hey, we still want you.' I got to see that the grass isn't always greener on the other side and signed back."