• Jimmy Rex

The Captain: 10 Lessons I Learned From Derek Jeter Watching His Documentary

If you are a baseball fan and haven't yet watched the new ESPN documentary on Derek Jeter, then you are in for a treat. I don't think I've turned on ESPN since football season ended, but as soon as I saw this was out, I knew I had to watch it.


In 1995, the same season that Derek Jeter became a rookie for the New York Yankees, I had become a huge Cleveland Indians fan. Both teams made the playoffs that year, so I always cheered against Jeter.

Watching highlights of his career took me back to many unforgettable memories as a baseball fan when I was a kid.


In 1995 I remembered watching Edgar hit the double down the line and Griffey raced home to knock the Yankees out of the playoffs. I remember my whole family watching that game and screaming. It was probably the last time I cheered for the Yankees cause I wanted Don Mattingly to keep playing and the Indians were up next.


Then in 1996, when Jeffrey Mayor robbed the Orioles in Game 1, I was at the golf course in the clubhouse watching, confused. 1997 was my favorite cause the Indians beat the Yankees closer Mariano Rivera when Sandy Alomar Jr. hit an epic home run to tie the game.

Then when the Indians went into a rebuild, it was the Red Sox and Yankees rivalry that kept me entertained for half a decade. So much so that I flew to Yankee Stadium for game 7 of the ALCS in 2004 when it looked like the Red Sox could possibly come back from being down three games to 0 and take the series. That turned out to be one of the most incredible weeks of my life.


Like I said, one memory after another... Jeter was always on the side I was cheering against, the evil empire, the Yankees. A funny thing happens with the passing of time and you realize that life can be a little boring without competition, a worthy adversary, or someone to chase. So even though you hated them at the moment, you appreciate them so much later. I think this is where I am with Derek Jeter.

We have been studying leadership for the past several weeks with my men's group, "We Are The They ." We have been looking for and talking about what makes a great leader. Here is a list of 10 things I noted while watching the documentary that made Derek Jeter "The Captain" of the Yankees.


What made him such a great leader:


  1. In 1995 he wasn't on the playoff roster, but they had him and a few other rookies in uniform and the dugout. Every player interviewed talked about how Derek was the first guy to greet them every single time they came off the field. He was the number one supporter and fan of the other players, even though I'm sure it was killing him not actually to be on the team.

  2. When he was young, he sought out the help of the veterans on the team. Daryl Strawberry, who had numerous run-ins with the law while a young player in the 1980s playing in New York for the Mets, was one person he listened to. Daryl told him who to stay away from and how to avoid these pitfalls as a young bachelor in New York with women throwing themselves at him every night. One night early in his career, he was invited to a club with P Diddy and J lo. He had been advised not even to take one little bite of the "apple" cause eventually; it leads you to a bad place. He had a game the next night and decided to stay in. There was a shooting that night amongst the group he would have been in and it could have tarnished his name or worse. He knew how to take his job and role with the Yankees seriously.

  3. He remained close to his childhood friends and family when he was drafted #6 overall and went on to win the Rookie of the Year in 1996 plus World Series. He knew the importance of staying grounded, which always showed throughout his career.

  4. In his 2nd or 3rd year, there was a play when veteran pitcher David Wells was frustrated with a few players and threw his arms in the air after an error was made. Derek called him out right there on the mound and said, "Hey, we don't do that shit here." He held those around him accountable.

  5. When the Yankees traded for Roger Clemens in 1998, he was probably the best pitcher in baseball at the time. The problem was that he had beef with several Yankees, including Jeter, whom Clemens had thrown at multiple times. When Roger arrived for the first practice, nobody knew how it would go. In his first session of live throwing, Jeter decided to get in the batter's box dressed head to toe in protective catcher gear. It loosened up everybody and immediately defused what could have been a tricky situation. He knew the value of being playful, forgiving the past, and self-deprecating as needed to bring together the team.

  6. After a fight with Chad Curtis, there was an incident in the locker room, surrounded by reporters, where Chad wanted to call out Derek and start a fight. Jeter was smart enough not to make it a public issue and defused it at that moment. They could keep it internal, and that year they went on again to come together as a team and win another World Series.

  7. After September 11th, with his city and country devastated, he went with teammates down to the streets and into the middle of everything to help. He mentioned in the documentary that he knew his role was to bring just a little joy to these people who had lost everything. It takes a humble leader to go and do that.

  8. He never buckled under pressure. In Game 4 of the World Series, with the entire weight of 9-11 and the city of New York on his shoulders, he got up in the bottom of the 11th inning and hit a walk-off, game-winning home run to tie the World Series at two games each. He had several clutch moments I could mention; this is just one.

  9. In a lose-and-go-home elimination playoff game against Oakland, up 1-0 in the late innings, there was a throw to the plate that overthrew both cut-off guys. Derek came over and grabbed it and flipped it to the catcher for the out to save the game and the season at that point. Most people said it was an instinctual play, but it wasn't. He had practiced for every scenario, including that once-in-a-lifetime moment when it presented itself; he knew exactly what to do and executed it perfectly.

  10. He never settled. Even after winning four world series in five years, he was devastated when New York lost in the 9th inning to the Diamondbacks in 2001. He expected to win and he never settled for less than that. And he used that as fuel and motivation even though every other player on the team seemed to accept the loss, Derek did not.

This documentary has two more parts that will be released later this week, but I just wanted to share a few lessons I learned from watching this show this past week. Alex Rodriquez, one of the best players to ever play baseball, was close friends with Jeter for the first parts of their career.



There was a big falling out because A-Rod let his ego get in the way and criticized Jeter as never having to lead a team because great players always surrounded him. The funny thing is that Jeter always won more than he did, while not statistically as impressive as Rodriquez because A-Rod was always more worried about how he looked to others while Jeter was winning. He did things that many will never know, but anyone on a team with Jeter or a team with an A-Rod knows the difference, and it becomes obvious which one became the champion over and over.