Holder's career has spanned the unrest of the 1960s and Vietnam War-era, the Reagan years and the fall of communism.
The only thing that stays the same is the students, Holder said.
Holder said he remembers a colleague submitting a study during a meeting to discuss the biggest challenges facing children. The meeting was in the 1980s or early 1990s. The study was dated 1956. It didn't matter. The kids don't change, Holder said.
"They're teenagers. They do dumb things, and you have to realize that I was a teenager once, and I got into trouble," Holder said.
Teachers have to love kids, he said.
"Sometimes, you're the only parent that these kids have that will listen. What does (St. Francis) say? Preach the Gospel, sometimes use words," Holder said.
The vicar of St. Luke's Episcopal Church in Brownsville, Holder plans to continue preaching. He even is considering pursuing his doctorate, just to keep up with his wife, Trudie, an administrator at the General Motors plant in Martinsburg, W.Va., who has hers.
"I don't know how people can retire and just sit down. It would drive me crazy," Holder said in a whisper.
Student Matthew Smith said Holder still knows how to make history relevant to new generations of young people.
"He really knows his history. He knows not only the things in the textbook, but other things, like the jokes, things that you're not really supposed to teach. He makes it fun," said Smith, who is planning to study political science and history at the University of Maryland at College Park.
Senior Becky Gisriel, 17, said she also is considering pursuing history because of Holder's influence. She plans to major in business at Roanoke College in Virginia.
Holder is a "great teacher," said Gisriel, who has signed up to take a history class next semester.
"I think that has to do with him, because I really enjoyed his class and I wanted to continue on with history," Gisriel said.
Holder and his 10th-grade honors world history class played a game of "I have, who has" - students stand up as they match proper names to the descriptions of significant historical figures and events - then discussed the Opium War and China's present-day economic dominance.
The class talked about movies and new rules for new drivers.
"These laws all pertain to you. Yes, it may not affect you, per se, but your brothers, your sisters, etc.," said Holder, who encourages students to get involved and take note of government decisions.
Principal John Davidson said Holder always has kept his teaching relevant to students.
"He's done so many things in the school and it's always been about kids, and we will miss him, and the kids will miss him," Davidson said.
Holder, who has stayed in touch with many past students, said he will miss his colleagues the most.
He and his wife are the parents of Trudi, 35, a computer programmer in Boston, and Anne, a former teacher, who lives with her husband, a U.S. Army first lieutenant, and children in Germany.