Long before he was a top executive with two world championship rings and a gleaming resume, Andy MacPhail was a Baltimore kid with baseball in his dreams and eye black streaked above his cheeks.
He was a 5-year-old who wouldn't take off his Orioles pajamas, an 8-year-old who constantly dragged around his Jackie Brandt two-tone bat and a pre-teen always searching for a game, even if it was against the bigger, older boys.
MacPhail, named last week as the Orioles' new president of baseball operations, may have been baseball royalty - his father and grandfather are Hall of Famers - but you wouldn't have known it by looking at the 1960s version. You certainly couldn't have eyeballed the unkempt 11-year-old and expected him to be making his living in well-tailored suits as an adult.
"He was an absolute disgrace," laughed Geordie French, a Baltimore businessman who played second base to MacPhail's shortstop for the Bearcats of the Roland Park Baseball League.
"He absolutely mortified his father, then the general manager of the Orioles," French said. "He'd have his pants legs hanging down around his ankles and his stirrups around his ankles."
Then there was the hat, the maroon felt Bearcats cap with the black hole in the back. It was singed when MacPhail left it on a cone-shaped reading lamp. He never patched it. Just played ball with a burn hole in his hat.
"He looked like hell and I looked good," French said. "But he was the one who could play."
MacPhail's family moved from Baltimore to New York when he was 13, but 40-plus years later the lesson still holds: Looks can be deceiving.
MacPhail, 54, has the button-down, spectacled, serious countenance of a banker. His mild-mannered, calculating demeanor seems more fitting for a big-time country club than a big league clubhouse. Yet he fits in with ballplayers and suits alike.
"I can't say enough about the guy," said Ed Lynch, a Cubs special assistant who spent six years as MacPhail's general manager in Chicago. "He's very smart, very consistent and predictable in the things that are good to be predictable about. He was always at his desk at a certain time. If you had a question, you knew where to find him."
Don't be fooled, say his friends in the game. Punctuality and responsibility are just part of the package. The guy knows baseball. He has supreme confidence. And he'll take charge.
"I really enjoyed my time with Andy. What you saw is what you got," former Cubs manager Dusty Baker said. "When he has to come down on you, he'll come down on you. When he has something good to say, he'll say that, too."
Jim Rantz, the Minnesota Twins' director of minor league operations, has known MacPhail for 25 years. He said he has a soothing influence on those around him - at least until 7:05 p.m. in the summers.
"I would say he is very calm except when the game gets out of hand. You don't want to be in his booth when that happens," Rantz joked. "He shows he has a temper when things aren't going too good. But Andy is usually under control."
French will never forget his first experience with the MacPhail family during spring training in the early 1960s. French, MacPhail and MacPhail's always-composed father, Lee, were sitting together in the back seat of baseball legend Larry MacPhail's cream-colored Cadillac as they drove around Florida.
Larry MacPhail, the grandfather, was driving, and cursing up a blue note while French's grandfather, then-Orioles principal owner Joseph Iglehart, was in the front passenger seat. Giggles from the two young boys in back were occasionally emitted.
French said his childhood buddy's personality has settled in nicely between Larry MacPhail's bluster and Lee MacPhail's unflappability - with a strong dose of both men's baseball love.
"[The Orioles] talk about wanting someone that's passionate," French said. "Well, boy, that really describes Andy when it comes to baseball."
Former Orioles first baseman Jim Gentile remembers the younger MacPhail as a "tow-headed boy who was around a lot and who has become one of the better men in baseball now."
Because of the way the game has changed, Gentile said, Andy MacPhail has a different operating style than Lee, who was the club's GM from 1958 to 1965. After his amazing 1961 season, in which Gentile had 46 homers and 141 RBIs, he requested a $10,000 raise, from $20,000 to $30,000.
The Orioles offered only $25,000, so Gentile held out and finally met with Lee MacPhail, who presented him with a contract for $29,000.
They spoke for 45 minutes, and finally, Lee MacPhail reluctantly reached back into his desk drawer and came out with another contract, this one for $30,000.
Gentile got what he wanted - but MacPhail made him work for it. And the next season, when Gentile again was an All-Star and hit 33 home runs, Lee MacPhail "wanted to cut me 20 percent."
"Boy, he was tough," Gentile said. "But he was fair, and good."
There's some old school left in Andy MacPhail. He said he still listens to advice from his father, who is 89 and living in Florida. But he probably patterned his management style a little more after the successful GMs of the 1970s and '80s such as Frank Cashen and Hank Peters. MacPhail said he's not one to congregate around lockers or text-message players.
"I'm not the type of guy, based on what I have been exposed to, that's going to be hanging around the clubhouse all the time," MacPhail said. "I like to make sure I am accessible to the players, but sometimes the best place to do that is hanging around the batting cage when we are on the road and it's kind of on an informal basis."
His style worked perfectly in Minnesota, where he was promoted to executive vice president and GM when he was just 33. He won the World Series the next year and again in 1991.
"He would give you some direction and let you do your job without any interference on his part," Rantz said. "All he wanted was to be kept informed so he wouldn't be surprised."
MacPhail took that business paradigm with him when he left Minnesota for Chicago's Wrigley Field in 1994.
His Cubs, baseball's traditionally lovable losers, weren't nearly as successful as the Twins, although they twice made the playoffs - the same number of times the franchise reached that plateau in the previous 50 years. And, in 2003, they were a handful of outs from going to the World Series before they imploded.
But by 2006, Cubs fans taunted him as "MacFail," and he and club ownership mutually agreed to his resignation at the end of last season.
His tenure, though, was hardly a failure, said John Stockstill, the Orioles' assistant GM and director of pro scouting who was MacPhail's scouting director with the Cubs.
"He came in the end of 1994 and by 2003 we were five outs from the World Series under his umbrella," Stockstill said. "He built the farm system and developed three No. 1 starters."
"That's baseball," Stockstill said. "But he had us set up for a five-year run."
Instead, MacPhail walked away, leaving a legacy of improvements to Wrigley Field and more longing for a title on the North Side of Chicago. He took eight months off, traveled with his wife, visited his father, read novels and historical nonfiction and did some projects for commissioner Bud Selig. Still, he couldn't shake the baseball bug.
"This game is going to go on without any of us," he said. "So I didn't know for certain I'd get back. I figured I would."
It happened sooner than he thought - in the city where he grew up throwing a football on his front lawn on Sunday afternoons while hearing the cheers of Colts fans from nearby Memorial Stadium.
But it was the Orioles that remained intertwined in his fabric all these years. He keeps a picture of Hall of Fame third baseman Brooks Robinson in his office and has a dog named Brooks. It's the franchise he always wanted to work for - he told friends that just a few years ago.
Now the kid with the hole in his hat and baseball in his heart has come home.
To try and build championship dreams and sports heroes for a new generation.