He has grown up in professional sports - the scion of a multigenerational major league family - and been closer than most to many of the great highs and lows of recent baseball history.
For instance, what are you supposed to tell your kids when they ask you at the dinner table about steroids, blood doping, point-shaving and dogfighting ... all during the salad course?
"I was thinking about that when I got up today," MacPhail said yesterday, "and I was thinking how fortunate I was to come home [Tuesday] night from a ceremony celebrating Cal Ripken."
Indeed, for one night, Baltimore was an oasis of sports integrity in a wasteland of scandal, but only in Baltimore was Ripken's "Hall of Fame Send-off" newsworthy enough to overshadow the shame of Michael Vick, the tainted home run chase of Barry Bonds or a basketball league suddenly masquerading as an episode of The Sopranos.
"I watched SportsCenter this morning," MacPhail said. "I came away frustrated that so much attention was given to the negative. Why not focus on what was a celebration of somebody who did the game a lot of good?"
It was a rhetorical question, of course, and MacPhail knows the answer.
He knows it's a bigger story when someone is accused of fixing a basketball game than when someone is celebrated for repairing a broken sport. That's just the bad-news-driven media world we live in.
This recent string of alarming events, however, has all but blocked out the sun.
The grotesque details of the Vick dogfighting investigation have dovetailed with the NBA referee scandal and a new set of revelations from the Tour de France - all of it piled on top of a decade or so of major league steroid angst.
By any account, the past week has been one of the most damning and disturbing in the history of big-time professional sports.
I can only imagine what it must be like for parents all over this country - heck, the world - trying to make sense of this with a generation of kids who no longer know what to think or whom to trust when it comes to sports heroes.
MacPhail's sons are 15 and 18, so they are old enough to see the forest for the trees. It's not so easy when you're dealing with children in the more impressionable age groups.
"I think if my kids were younger, I would try to remind them that what's getting all the attention is the exceptions," MacPhail said. "There are a lot of athletes out there who you would be proud to have marry your daughter or your sister. But the amount of media that is focused on sports now, you can't help but see a lot of this kind of stuff."
It has to spawn a sort of mass-media moral relativism - where if the big, rich sports celebrities are doing it, what's the big deal? - which is why it's important for parents to turn these tawdry tales into teaching moments.
"I try to remind my kids that what you have to be responsible for is your own behavior ... how you live your own lives," MacPhail said. "There will be no harsher judge than the guy you see in the mirror."
Which brings us back to Tuesday night and how refreshed we all felt after the Orioles celebrated Ripken's pending induction into baseball's Hall of Fame.
The traffic headed to upstate New York this weekend should serve as testament to what we truly value in our sports heroes.
If you can't make the trip, make sure the TV is tuned to Cooperstown on Sunday afternoon.
Ripken and Tony Gwynn are exceptional, but tell your kids they are not the exceptions.
Listen to Peter Schmuck on WBAL (1090 AM) at noon Saturdays and Sundays.
