In 1956, the 20-year-old son of a Latin American baseball legend had come home from a summer playing in the minor leagues in Texas with a startling confession.
"I'm done," he told his father. "I can't do it anymore. I quit."
The father, a tall, gentle, dark-skinned man named Santos -- a barnstormer who had played and managed in Mexico and in his native Cuba -- calmly looked at his son and asked what had happened.
What a terrible summer it had been, the son explained. The people in Texas had said cruel things to him, insults, merely because of the color of his dark skin and the country of his birth, Mexico. All he had done was play minor league baseball. He had meant no harm. But he often was forced to stay at a different hotel than his team, and he usually was not allowed to eat in the same restaurants as his mates. It was dehumanizing and degrading.
"I want to remind you of a promise," Santos responded calmly. "I let you leave school to play baseball because you promised me that you were going to do what it took to get to the majors. What happened to that promise?"
The son, at that point, knew he couldn't quit. His old man was right.
Two years later, Ruben Amaro reached the major leagues, where he would play 11 seasons with the Cardinals, Phillies, Yankees and Angels. After his playing career ended, Amaro became a coach for the Phillies and White Sox, then a scout and front-office advisor for Philadelphia, then Houston. In his heart, he had always wanted more. Amaro believed that he could be a good manager or perhaps even a general manager. Most considered him one of the smartest people they had known in the game. But it was not meant to be. As his experiences in Texas had taught him, baseball was not always open-minded.
"I was not only Latin, but my family was also a bit dark," Ruben Amaro said. "My time came too early."
At the end of a particularly grueling day in spring training in 1998, Ruben Amaro Jr. was approached by then-new Phillies general manager Ed Wade. Usually those types of meetings aren't good, especially for a fourth outfielder trying to cling to a major league career.
Wade asked Amaro about his post-career plans, the type of question that almost always means the end of a player's time on a team. But Wade didn't have bad intentions. Wade, who was the Phillies' assistant general manager from 1988 to 1997, had known Amaro since Philadelphia had acquired him in 1991 in a deal with the California Angels for Von Hayes. Wade was also in then-Philadelphia general manager Lee Thomas' office when Amaro called in early May 1996 looking for a job after he had been released by the Blue Jays while he was at Triple-A Syracuse.
"Do you have anything for me?" he asked.
"Ruben, I'm not sure; let me see and I'll get back to you," Thomas responded.
Literally later that day, one of the Phillies' outfielders got hurt, and Thomas and Wade called Amaro.
"Ruben, I got a job for you," Thomas said.
"OK, I'm still in Syracuse, I can be in Scranton in two hours," Amaro responded.
Thomas replied, "Ruben, it's actually a job in the big league with us."
"Oh, that's great," Amaro said, "I'll have my agent call you."
Thomas said, "Ruben, if you have to have your agent call us, then don't come."
"I'll be there in three hours," Amaro said.
So Wade always had known how much Amaro cherished playing the game. But as Amaro's .634 OPS in 1997 had shown, his career appeared to be ending. In his mind, Amaro had thought perhaps someday he would make a pretty good manager or coach, just not then. But what Wade said next floored Amaro.
Wade offered Amaro the team's assistant general manager position on the spot. Frankly, the whole thing was a gamble. Amaro had no front-office aspirations. Wade had had no idea whether Amaro was a good talent evaluator because he had never asked him his opinion on a player. Surely he knew nothing about contract construction or building an arbitration case, two of the main tasks of an assistant general manager.
But in the younger Amaro, Wade saw a Stanford-educated, Philadelphia-born-and-bred, Spanish-speaking player who came from a baseball family. Ironically, some of the qualities that had kept Ruben Amaro Sr. from advancing further in baseball were now some of the qualities that made his son such an attractive front-office candidate.
"Hey, let me try to play the season out," the younger Amaro told Wade. "I know my career might not be lasting long, but if I can have another good year off the bench, then maybe I can buy myself another couple of years in the majors."
The first player evaluation the younger Amaro was asked to make as a front-office executive candidate turned out dreadful. He had misjudged himself. That season, Amaro hit .224 with a .486 OPS. Midseason, after several long talks with his father and his brother David, Amaro decided to accept Wade's offer. He would become Philadelphia's assistant general manager at the end of the 1998 season.
"I'm actually glad that I was as bad as I was that year," Amaro said. "It helped solidify the fact that I absolutely made the right choice. I mean, I was done."
A few days after the season ended, the Phillies made the move official.
"I know I surprised a lot of people in the industry when I hired him," Wade said. "I had a couple of veteran baseball people frankly question why I would do that, because there were a lot of people who at the time were serving their apprenticeship and working in that direction for opportunities like that. I just felt it was the right thing for the organization."
Wade, who had waited almost 13 years before being named Thomas' assistant in 1988, understood some of the complaints. He just believed in Amaro so much that he had left the assistant general manager job open for the entire 1998 season in case Amaro would change his mind.
"There might have been people who were skeptical, but those were just people who were jealous," said Omar Minaya, Amaro's friend and former Expos and Mets general manager.
There are no more skeptics. In the three seasons since being named the Phillies' general manager after the 2008 season, Amaro is arguably the most daring executive in the game.
"He believes in going for it, and that's admirable," Minaya said. "He's not afraid to give three or four prospects up for quality. A lot of people are scared. He's not."
Not all of Amaro's moves are beyond reproach, but he runs his team without fear of criticism or failure. He has handed out monster contracts that have been publicly ridiculed. He has traded away a pitcher after an almost-perfect postseason, then reacquired him later in a surprising last-minute free-agent grab. He made a daring trade to acquire the best pitcher in baseball. He acquired the best hitter available at this year's trade deadline.
"I'm an aggressive personality," Amaro said. "I like to make things happen. I also have a pretty good understanding what this fan base is about. Success kind of breeds success. Expectations continue to rise and don't stop rising. At some point we're going to disappoint some people, but you couldn't disappoint any people more than I could disappoint myself. I remember telling my kids when I got the job, 'Right now, they're going to like the Phillies a lot, and they like your dad. There's going to be a time when your dad isn't going to be very well-liked. So prepare. I hope you're much older when that happens.'"
Most importantly, Amaro has helped turned the Phillies into the best franchise in the National League. Even his biggest doubters would acknowledge now that Amaro didn't inherit a team built by Wade and Hall of Fame executive Pat Gillick and simply rest on their work. Philadelphia -- with players such as Roy Halladay, Cliff Lee, Hunter Pence, Roy Oswalt and John Mayberry Jr. -- strongly carries Amaro's imprint.
On the rare days when Santos was at home and not on a baseball field, he had simple instructions for his sons.
"I don't want to see bats and gloves in the house," Santos told them. "I want to see books."
I'm an aggressive personality. I like to make things happen. I also have a pretty good understanding what this fan base is about. Success kind of breeds success. Expectations continue to rise and don't stop rising.
”-- Ruben Amaro Jr.
The boys resisted, of course, but they had no choice but to listen.
"He was too tall for us to argue with," Ruben Amaro Sr. said.
Despite all that he had given the game and what the game had given him, Santos did not want his children to become baseball players. The lifestyle was too difficult. First, there was the constant travel. Santos spent most of his life shuffling between Cuba and Veracruz, Mexico, until he left Cuba for Mexico permanently in 1951. Second, it was a modest living. It was a struggle to provide his children with enough to eat. His wife, Josefina -- a Mexican woman whom he had met because she played on a women's baseball team that often had its games before Santos' games -- understood the love of the game and the sacrifices the family had made, although it didn't make it any easier.
Both Santos and his wife agreed that education would be a better option for their children.
Santos had been a good student in Cuba with an interest in accounting. But he often quarreled with teachers when they didn't allow him time for baseball practice. It was a decision he later regretted.
But Santos allowed the world to be his university. His travels taught him about life. He often buried himself in books and tried to soak up as much knowledge as he could.
Yet for all the effort he had made, Santos' children loved baseball as much as he did. His son Ruben was a standout player who attracted scouts' attention. One day a scout from St. Louis offered Ruben a professional contract. Santos grudgingly allowed his son to sign and leave school on the condition that he would make it to the majors.
As Ruben Amaro Jr. headed into his senior year of high school in 1982, his college future was very much undecided. Surprisingly, Amaro had grown up as a standout soccer player despite his family's baseball background.
Yet he had never been able to separate himself from his family's game. In 1980, when his father was a coach for the Phillies, Amaro was given an opportunity to be the team's batboy. Spending time in the clubhouse rekindled his love for baseball.
During high school, Amaro had gotten an offer to train with a soccer team in Europe, but his mother didn't want him to go so far away. It was for the best, anyway. Amaro had bought into the family trade, even though his father had tried to shun his sons away from the sport, as Santos had done with him.
Instead of buying a house, Amaro's parents rented a duplex so he and his brother David could attend the prestigious William Penn Charter School to have a strong academic background in case they wanted a career outside of baseball.
But it was inevitable that the sons would play baseball.
Because he had focused so long on soccer, Amaro was not a nationally recognized high school prospect. Most of the offers to play baseball that Amaro received came from schools -- Duke, Vanderbilt, Princeton -- that valued his education as much as his baseball skills. Stanford coach Mark Marquess recognized Amaro's rich family baseball history, so he invited him to play at Stanford, although he could not offer him a scholarship and he would not guarantee playing time.
"We expected even though he wasn't highly recruited that he could help us," Marquess said.
Amaro visited Stanford and fell in love with the school. He decided to accept Marquess' offer despite having no assurance as to how he would fit into the team.
While they packed his car for him to drive to California, Amaro told his father, "I'm going to Stanford, and I'm going to make the team."
Ruben Amaro Sr. thought his son was being boastful.
"What? How is that going to happen if you've barely been playing?" his father asked.
"Not only am I going to make the team," the younger Amaro responded, "I'm going to make it to the majors."
Amaro had grown up a confident kid, a theme that would continue for the rest of his life. When he scored goals in soccer, he often celebrated as though he had just helped his team win the World Cup. As a kid, he would ask to play sandlot ball with David, who was 3 years older, and his friends. Because he was so athletically gifted, the older kids accepted, even though Amaro often would remind them how talented he was. When his confidence irritated the older boys, he sought protection from his big brother.
At Penn Charter, Amaro was only 5-foot-10, 150 pounds, while David, who would play in the minors before a wrist injury ended his career, was built like his father and Santos: tall, dark and strong. But Amaro was never intimidated by his lack of size.
When he arrived at Stanford, he immediately earned Marquess' respect with his work ethic and his knowledge about the game, although he wasn't shy about boasting about how he excelled at all baseball things. Some of the older players did not appreciate his ego, but they could not complain about Amaro as a teammate because he was talented and unselfish, and he worked hard.
"As good of a player as he was or he might have been, he was a much better player in his own mind," Marquess joked. "But that's what made him special."
Marquess appreciated Amaro's demeanor. Often, when Amaro came back to the dugout after an at-bat, he would tell his teammates that the opposing pitcher wasn't throwing very hard. It helped relieve some of the tension. His attitude gave his team an edge.
Amaro also had numerous conversations with Marquess about team strategy, a rarity for a college player. Although on the surface it might have seemed disrespectful for a player to inquire about Marquess' decision-making, the Stanford coach welcomed the discussions. He respected Amaro's opinions because of his baseball upbringing.
"Ideally, you'd like to have a guy like Ruben on every team because of his background," Marquess said. "He had instant credibility."
By the time he finished at Stanford, Amaro Jr. was an All-Pac-10 player who had been a prominent member of two national championship teams. In his senior year, he hit .344 with 19 doubles, 6 triples, 7 home runs and 38 steals. The California Angels drafted him in the 11th round in 1987, and he made his major league debut four years later. His promise to his father had come true.
In 2001, Amaro and his then-wife and two young daughters got on a plane and set off for Veracruz, Mexico, to visit Santos. The old man was 93, and with his failing health, nobody knew how much longer he had left. Amaro's wife had suggested the trip so that their little girls could spend one last time with their great-grandfather. Out of fear that Santos might not live until the winter, Amaro took a week off during the middle of the season.
It was a wonderful experience. The old man was still a gentle giant, and the girls loved him. In the streets when he walked by, the people called him "Don Santos" out of respect for all that he had done in the community with baseball.
Amaro -- a mixture of Cuban, Mexican and Russian Jew -- had never struggled with his identity, but he had at times been weighed down by the family name, which caused some of his early struggles with the Phillies.
"I really had a tough time creating and dispelling my own expectations about what kind of player I should be," Amaro said. "I had some success early, and I didn't take care of myself too well insomuch that I put a lot of heat on myself to perform. It was difficult being at home and dealing with having the same name as my dad and having to play on the same team."
Maturity helped Amaro accept who he was and to become his own man and not live in his family's shadow. He had forged his own path, but he was proud of the Amaro name, too. Santos died later that year knowing his baseball legacy would continue through his grandson.
As soon as he accepted the assistant general manager job, Amaro did his best to acclimate himself well so that there would be no more reasons for skepticism. That wasn't necessarily for his own confidence, because he never really cared what people thought, but more so that he wouldn't fail for Wade, who had truly taken a chance on him.
Wade immediately threw him into the job, assigning him tough tasks such as arbitration hearings and the signings of minor league free agents. Through these tasks Amaro met agents, scouts and players, and he learned to negotiate.
During one of his first visits to Shea Stadium after accepting the job, Amaro quizzed Minaya, then the Mets' GM, during batting practice. He asked questions and offered opinions. He did the same with other executives whom he knew well.
Amaro spent his first few years as assistant general manager walking back and forth between his office and Wade's office to ask questions. In time, Amaro grew into the job and became a vital staffer for Wade and Gillick.
In 2002, he helped persuade Jim Thome, with whom Amaro had played with in Cleveland, to sign with Philadelphia. In 2004, he suggested that the Phillies hire Charlie Manuel, who had been his hitting coach in Cleveland. Amaro remembered that Manuel would spend time in the batting cage with every player, not just the superstars. Manuel was willing to work with whoever wanted to work. It was that type of person Amaro believed Philadelphia needed for a manager. In 2005, Amaro persuaded then-Rule 5 pick Shane Victorino to accept a minor league assignment after spring training.
Amaro also played a leading role in Jimmy Rollins' contract extension in 2005. And Amaro was involved with countless other deals and negotiations.
When Gillick retired after the Phillies won the World Series in 2008, Amaro easily transitioned into the head GM job. His first trade was sending failed prospect Greg Golson to the Rangers in exchange for Mayberry, who has become a important cog for this year's Phillies team.
Amaro was the perfect amalgamation of his two mentors. He picked up on all the technical aspects of the job -- contract specifics, arbitration hearings -- from the more reserved Wade while mirroring gregarious Gillick's people skills.
During the first front-office dinner with Gillick after he took the job, Amaro was astounded when Gillick invited a restaurant employee, who wanted to give his opinion on the team to sit with the group to talk about Phillies baseball.
"That was an epiphany for me," Amaro said. "You can gain a lot of information from anybody."
As the top man, Amaro ran his team the same way. He listened. During the 2009 season, Amaro and senior adviser Dallas Green were in assistant GM Scott Proefrock's office when Proefrock mentioned that he had read a report on the Internet that Martinez had been throwing well in the Dominican Republic. Immediately, Amaro called Martinez's agent and set up a couple of private workouts. Shortly after, the Phillies signed Martinez, and he ended up pitching for them in the World Series.
"It's by far the best organization I've been associated with," said Proefrock, who previously had worked with revered executives such as John Schuerholz and Andy MacPhail.
A favorite part of Amaro's job is interacting with players.
"When are my first three guys in the lineup going to start hitting?" he asked once after walking into the clubhouse.
Although Rollins, Victorino and Chase Utley all laughed, the players knew the joke had a message: They had better start hitting.
Being part of the early-1990s Phillies also had given Amaro a lesson in the importance of clubhouse dynamics.
On a team flight during his rookie year in Philadelphia, a single Amaro fancied the stewardess and tried to see whether he could arrange a date. He wrote a flirtatious note that included the phrase "I'm the total package," and he leaned over to give her the piece of paper. Unfortunately for Amaro, the note was intercepted by relief pitcher Mitch Williams, who read the note out loud to the rest of the team. From then on, Amaro was called "total package" or "TP" for short, the perfect moniker for a player who often had rankled teammates with his confidence. That type of ribbing was common in that clubhouse, and the players on the team truly believed that such interaction created unity and had led to the team's success.
Those experiences shaped how Amaro built a clubhouse.
"Was he the total package as a player?" said Williams, now an analyst for the MLB Network. "Time showed that he probably wasn't. But I wouldn't hesitate to call him a total package as a GM."
Amaro has assembled a team with the best record in baseball, perhaps the best team the Phillies have had during their current winning spell that on paper seems to surpass even the 2008 World Series champions. These Phillies are Amaro's team. He's the architect. But there are still tasks to be accomplished and championships to be won.
For him, the time has almost come.
Jorge Arangure Jr. is a senior writer for ESPN The Magazine.