Orlando Cabrera was stunned when he was traded from the Montreal Expos to the Boston Red Sox at the trading deadline in 2004. The slick-fielding shortstop still remembers every detail of his conversation with Expos’ manager Frank Robinson on July 31. 
“Frank called me into his office and he said, ‘I’m going to give you 25 guesses of where you’ve been traded.’ I started running through the teams and figured it’s not the Yankees because they have Jeter at shortstop; it’s not Boston because they’ve got Nomar, and it’s not St. Louis…
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“After about ten wrong guesses, Frank said, ‘You’ve been traded to the Boston Red Sox.’ I had been standing up because I wanted to race to catch a plane, but when he said that, I sat down. I thought, oh, my gosh, I’m in trouble.”
Orlando Cabrera realized that he had been selected to replace a Red Sox legend, and he was being asked to supplant Garciaparra in the midst of a tight playoff race. Orlando was a highly regarded player in the National League, and he had won a Gold Glove at shortstop in 2001, but he knew that he would be in a very bright spotlight in Boston.
CARTAGENA COLOMBIA NATIVE
Orlando Cabrera was born in Cartagena, Colombia, on November 2, 1974. Cartagena is a city of about 900,000, located in the Caribbean Coast Region. It is a port city and a popular tourist destination.
Soccer is the national passion in Colombia, but Cabrera had baseball in his genes. His father, Jolbert Cabrera, Sr., was a player and a manager, and he was the first MLB scout in Colombia. “I learned my passion for winning from my father. He hated to lose and so do I.
“But I would have to say that the most important person in my life was my mother Josefina. She was a teacher for 44 years and she would still find time to be at my baseball games and my brother Jolbert’s. She really knew her baseball.
“I asked her later why she pushed us to play baseball all the time and she said it was because she knew we wouldn’t get into trouble if we were busy playing ball. She was always looking out for us.”
According to baseball-almanac.com, there have only been 13 native Colombians who have made it to MLB: Orlando and his older brother Jolbert, who played all or parts of 8 seasons in MLB, are two of them. “My brother Jolbert is two years older and he was bigger and more athletic than me. He was the better player when we were younger,” he insists, “so I had to work harder.”
Asked when he first thought about a career in the major leagues, Orlando answers, “I was 14 when my brother signed to play professional baseball. I thought if he could make it maybe I had a chance.”
Orlando attended 15 tryout camps, but his small size held him back. “I had enrolled in college but after two months a scout contacted me to sign with the Montreal Expos.”
PROFESSIONAL CAREER
Orlando’s first stop was the Dominican Summer League where he played against David Ortiz, who had just signed with the Seattle Mariners. In 1994, at age 19, he was invited to the Expos’ spring training complex and he made his first trip to the United States.
“That was quite an experience,” he says. “My brother Jolbert was in the Expos’ minor league system, so that was a big help. He helped me settle in and he taught me how to order food.”
But at the end of spring training Orlando was on his own. “I had a buddy, Jose Macias, from Panama, who I had played with, and we helped one another out,” he recalls.
Cabrera progressed steadily through the Montreal minor league system, playing well at each stop. His fine play at Triple-A Ottawa earned him a September call-up with the Montreal Expos.
Orlando still recalls the details of his first start in the Major Leagues. “It was against the Braves and Greg Maddux was the pitcher,” he says. “I used to watch him pitch on the super-station [TBS] and I knew he always pitched outside so I was ready. I got two hits against a future Hall-of-Famer in my first game!”
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In 1998, he played 79 games with the Expos, and from 1999 on he was Montreal’s regular shortstop. In 2001 he received the Gold Glove as the National League’s best fielding shortstop and in 2003 he hit a career-best 17 home runs. “I enjoyed playing in Montreal,” he says, “but we never had the resources to compete.”
WELCOME TO BOSTON
Orlando Cabrera may have been concerned about replacing a Boston icon, but Boston’s two best starting pitchers were thrilled to have him. Pedro Martinez said at the time, “I remember Cabrera as a young, good steady player at shortstop in Montreal, but he’s gotten even better over the years. He’s going to be a good player for us.”
Curt Schilling, who had played against Cabrera in the National League, echoed Pedro’s positive comments. “I know Cabrera from playing against him and he’s one of the best shortstops in the game. He can hit and he can play good defense for us.” He added, “Getting Orlando is a game changer for me.”
Orlando’s first day with the Red Sox was a memorable one. He arrived one hour before game time and he hit a home run in his first at-bat with the Red Sox, only the eighth player in team history to achieve that feat at the time. “That was a great feeling,” he emphasizes. “I began to think that maybe I could do this.”
The Red Sox were a new team for Cabrera but there were a number of familiar faces. Bench coach Brad Mills had filled the same role for the Expos in 2003, and he knew minor league instructor Tommy Harper from Montreal as well. “I knew Manny, I had known David [Ortiz] for a long time and I knew Pedro [Martinez] from the Expos. They all helped me to get comfortable.”
After seven games on the road the Red Sox returned to Fenway Park for a three-game series against Tampa Bay on August 9. Asked what surprised him about his new baseball home, Orlando responded, “A lot of things. I had played in Fenway during interleague play but that was before the sellout streak at Fenway. I was amazed by the crowds and their intensity.”
And Orlando acknowledges he was like a kid in a candy store when he saw the resources available to Red Sox players. “In Montreal we didn’t even have a video coordinator. At Fenway I could go into the dugout tunnel and watch my last at-bat on the computer. Whatever we needed to help us was provided.”
The other surprise for Cabrera was the extent of the daily media coverage in Boston. “In Montreal we had three reporters covering us. One was actually a tennis expert and another wrote in French. All of a sudden the media was everywhere.
“Pedro Martinez gave me some good advice. He said, ‘Do the interviews but don’t ever read a paper here.’ So that’s what I did. I would be in the on-deck circle and fans would yell, ‘We love you Orlando. We don’t care what the papers say.’ I wondered what in the world the papers were saying, but I never looked.”
THE DRIVE FOR THE PLAYOFFS
By mid-August Cabrera had found his rhythm and he began driving the ball with authority. He credits Red Sox hitting coach Ron Jackson for helping him find his groove. “I was hitting about .230 and Papa Jack said, ‘Orlando, I want you to concentrate on pulling the ball. You’ve got that wall out there in left field, and if the ball is in the zone I want you to pull it.’ It was like a light went off from there on.”
Jackson’s advice paid off on August 17 in a game against Toronto when Orlando stepped to the plate in the ninth inning at Fenway Park with the game tied 4-4. Cabrera lined a double off the Green Monster and Johnny Damon raced home with the winning run. “That felt so good,” Orlando remembers. “There is nothing better than helping your team win a game.”
Orlando continued to shore up the Red Sox defense and contribute at the plate, and the Red Sox continued to win. An extra innings win over the Orioles on September 19 is one of his favorite memories.
“I had gone back to Colombia for to help with a family medical issue and I traveled all day to get back to the game,” he recalls. “In the twelfth inning I hit a walk-off home run. The fans went crazy and I was mobbed at home plate by my teammates. That’s a great memory.”
In addition to Cabrera, the Red Sox also added Doug Mientkiewicz and Dave Roberts at the trading deadline in 2004. From that point on the team went 42-19, to win the AL Wild Card. Orlando helped to improve the Red Sox defense while batting a solid .294.
POSTSEASON MEMORIES
When the ALDS against the Anaheim Angels began Cabrera was determined to enjoy every minute of the playoffs. “I had come up to the big leagues in 1997 and this was my first time in the playoffs,” he says. “I tried to slow things down so I could remember everything.”
In Game Two in Anaheim Orlando doubled with the bases loaded in the ninth inning to blow open a tight ball game, leading to an 8-3 Red Sox win. Boston swept the Angels in three games and the stage was set for a Red Sox-Yankees ALCS.
Cabrera’s strongest memory of the historic series against the Yankees is the classic Game Four match up. “My good friend from Columbia was covering the Series for television and radio. He told me he had made reservations to fly home after Game Four. I told him: ‘Don’t do it!’
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He said, ‘Are you crazy? It’s over.’ I told him ‘This is baseball. It’s different every day. It is not over.’
“When I got the clubhouse every player was going about their business the way they do before every game. I knew then that this team believed in itself and that no one was panicking. I felt the same way.”
After the historic Red Sox comeback Orlando said, “We didn’t think any team could possibly beat us. But then we looked at the Cardinals lineup and realized that they were a very good team.”
Asked how it felt to be playing in the World Series, Orlando says, “It was an unbelievable thrill. Schilling [Curt] told us to look at the World Series patches on our uniform sleeves and to soak it all in.”
The St. Louis Cardinals were a very good team but they were no match for the streaking Red Sox in the World Series. After winning the opener at Fenway 11-9, Red Sox pitchers Schilling, Martinez and Lowe dominated St. Louis hitters in the next three games and Boston had its first World Championship in 86 years. 
Reflecting on the 2004 World Series win in a recent interview, Orlando says, “Winning the World Series was the greatest thing that happened to me in my baseball career. I am proud of all my accomplishments but I was always about helping my team to win. That World Championship was my greatest thrill by far.”
LATER YEARS
Orlando Cabrera signed a four-year contract with the Angels before the 2005 season. “I had played professionally for a long time and I had finally qualified as a free agent,” he says. “This was my chance to earn some security and the Angels made me the best offer. It would have been nice to stay in Boston but I had to take care of my future.”
Cabrera played seven more seasons in MLB and he returned to the playoffs five times. But he never made it back to the World Series. “I thought I would,” he says referring to the World Series, “but I never did. I tried,” he says smiling.
Orlando Cabrera retired from baseball after the 2011 season. During his 15 years in MLB he played in almost 2,000 games and he had over 2,000 hits. “In my last season my mind was as quick as ever but my body wasn’t as quick. I love baseball too much to ever play at less than 100%,” he emphasizes. “It was time.”
Asked how he adjusted to life away from baseball, Orlando responds, “I adjusted immediately. My daughter McKenna was born on the last day of the 2011 season and so I was busy with her right away. And then my daughter Livia was born two years later so I have been busy with my family from the day I retired.
ORLANDO CABRERA TODAY
Today Orlando Cabrera and his wife Katie live in southern New Hampshire with McKenna, who is five years old, and Livia who is three, and a new-born. He is in close contact with his two daughters from his previous marriage, Orhel (19) and Mitchelly (16).
When he is not busy with his family or reading, he is a consultant with Wealth Management. “I try to educate young players on managing money and I love it,” he says. “Many players sign at 17 or 18 and they don’t know anything about finance.”
There is one moment at Fenway Park that really stands out in Orlando’s memory. “When I came back to Boston with the Angels in 2005, I didn’t know what to expect. When I came to bat for the first time Varitek said, ‘Get ready.’
“I didn’t know what he meant but when they announced, ‘Now batting for the Angels, number 18, Orlando Cabrera,’ every fan stood up and started cheering. Tek got out of his crouch so the moment could continue and I appreciated that.
“You have to understand, I wasn’t the kind of player who got standing ovations or curtain calls,” he insists. “I did the little things that helped my team win. That ovation really meant a lot.
“I will never forget that moment. And I will never forget the great fans of the Boston Red Sox.”
Portions of this article appeared in the September edition of Red Sox Magazine. To subscribe to Red Sox Magazine click here.
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