It was a question, perhaps, unlike any other in baseball history. At a Boston Red Sox team event last month, a pitcher asked a first-base coach how close he had come to trading for him.
Ruben Amaro, former general manager of the Philadelphia Phillies, assured Henry Owens that he never believed he would send his prized trade chip, pitcher Cole Hamels, to Boston. The Red Sox held tight to their best prospects, and Amaro dealt Hamels to Texas.
“But I liked you,” Amaro told Owens, scanning the room for others he had wanted. “And you, and you, and you.”
Now Amaro wears the same uniform as the players he once coveted. His unusual career path has taken him from the executive suite in Philadelphia to the coaching box in Boston. Except for a ceremony to close Veterans Stadium, Amaro guessed, he had not worn uniform pants before this camp since his final game as a player in 1998.
The Phillies named him assistant general manager after the 1998 season, and Ed Wade, his boss at the time, told him to make a clean break from his old life. Amaro was suddenly preparing salary arbitration cases against old teammates, but he enjoyed the role. He helped build a championship team in 2008, took over as general manager for Pat Gillick the next season, and fortified three more playoff rosters with deals for Cliff Lee, Roy Halladay and others.
After the Phillies fired him in September, Amaro could have pursued work in television or business, or in another front office. When the Red Sox offered the coaching job, Amaro sought advice from Gillick, who encouraged him to take it.
“I think he’s going to be a manager,” said Gillick, a Hall of Fame executive. “He’s a smart guy, he’s bilingual. Consequently, I think he’s going to get an opportunity.
“At least to me, if he gets a couple of years under his belt, he’s going to be more qualified than a lot of people managing right now. There are a lot of people that had no experience whatsoever and got an opportunity to manage in the big leagues.”
Amaro, 51, does not lack experience. As a teenager, he was a bat boy for the 1980 Phillies, who won the World Series with his father, Ruben Sr., as the first-base coach. Amaro later starred at Stanford and played parts of eight seasons in the majors. He converted from infield to outfield to do it, a transition that appealed to Red Sox manager John Farrell, a former teammate with the Cleveland Indians.
Farrell has put Amaro in charge of the Boston outfielders, including Rusney Castillo, a $72.5 million enigma the Red Sox signed from Cuba in 2014. (Amaro pursued him for the Phillies, too.) With Castillo, Jackie Bradley Jr., Chris Young and especially Mookie Betts, the Red Sox outfield could be strong. That group is his main focus now.
“I’m here a little bit earlier, but I also get to be home a little bit earlier,” Amaro said, comparing his jobs. “Listen, as far as my intensity and desire to do my job well, I don’t think that’s changed all that much. I want our outfield to be the best outfield in baseball. We have a chance to do that.”
Amaro was widely ridiculed at the end in Philadelphia. He was slow to embrace analytics, the roster decayed, and fans lost patience. As a native of the city, Amaro — who still lives there — understood the criticism. Asked what he misses least about his old job, he cited the mundane task of providing injury reports to the news media. The scrutiny took a toll, he said, but not a big one.
Now, with a much lower profile, Amaro delights in the little surprises of clubhouse life. Former Red Sox pitching star Luis Tiant recently told Amaro that his grandfather Santos Amaro was Tiant’s first professional manager, for the Mexico City Tigers in 1959. Amaro wears No. 20, his father’s number as a Phillies shortstop in the 1960s.
“It’s just another great opportunity for a good baseball guy,” said Brian Butterfield, the Red Sox’s third-base coach. “He looks real comfortable with what he’s doing.”
There will be adjustments. Amaro has not lived in Boston since his summers in the Cape Cod Baseball League and has a dubious plan to drive to Fenway Park from his nearby apartment. He has little experience with a fungo bat, the essential thin-barreled coaching tool. And he may not be the team’s best batting-practice pitcher.
“My BP has been probably a 40 or 45,” Amaro said, ranking himself on baseball’s 20-to-80 scouting scale. “But I’m throwing left-handed right now. I’m ambidextrous. I threw three or four days in a row, and my right arm started barking.”
Better a barking arm than a barking talk-show host, you might say, but Amaro’s legacy in Philadelphia is not complete.
He could not snag Owens, Betts or catcher Blake Swihart for the Phillies, but the prospects from the Rangers give his former team hope.
“I’ll be peeking at them,” Amaro said.
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