Teaching is a hard job, especially in this day and age, and one of the only jobs that is more difficult than teaching is subbing. Hector Cobb has subbed for 42 years, taught for four, and has seen it all.

Born in northern New York near the Canadian border, Cobb is 71 years old and resides at his home in the Hollywood neighborhood with his wife of 25 years. He often substitutes at Cleveland and other schools in the PPS district, but mostly sticks to high school saying, “I did it all – elementary, middle and high school, and it was quite easy to learn that I loved high school.”

Cobb has taught all around the world. He started his teaching career in the Virgin Islands, and his experiences there are hardly what one might imagine as the typical introduction to teaching.

Prior to teaching, Cobb traveled to Spain in his third year of college, where he met a dictator: Francisco Franco. 

Cobb was placed with the family of Franco’s education minister, so when the opportunity arose to meet Franco, he took it. 

He went to the Royal Palace where he had to get down on one knee before Franco, kiss his hand, and swear loyalty lest he face a six-month jail penalty. 

“It’s better to kiss the hand of the man than spend six months in the can,” Cobb said. 

After graduating from the State University of New York at Potsdam in 1976 with a BA in history and Spanish, Cobb lived in Syracuse, and said at that time he was “holding a variety of odd jobs, which I hated most of them, like working at KMart, at the gym or cleaning the toilets, working in a bowling alley vacuuming, working the graveyard shift.” 

He did this for three years while applying everywhere possible to try and get a teaching position. 

“Since I was alone – my family had passed by the time I was 15 – I didn’t care where I went. I just wanted to teach. So I just started sending applications globally. I sent some to Mexico, Chile, to Argentina, and to the Virgin Islands,” Cobb said.

 Eventually, he got a call from a school in the Virgin Islands that had offered him a teaching position at one of their elementary schools. There he taught Spanish and got his first glimpse of his job, which would end up making for many good stories.

“Now, the first day of teaching, I had a very weird experience. In the Virgin Islands, if you fail one subject, say you failed math in the fourth grade, they held you back. Some of these kids got held back constantly. I had 16-year-olds in the fifth and fourth grade,” Cobb said.

When Cobb started teaching his class, he noticed that one of his older students, probably around 15 or 16, was wandering around the classroom. He kindly asked the student to sit back down, but the boy walked up, picked Cobb up and threw him out the window.

“Luckily, this was only a one-story school, and it had wooden shutters, because in the Virgin Islands, it never gets below 70 degrees, so it broke a few shutters. I just fell on the ground, got mud all over my pants, and I went back in the building through the broken window, called the security and said bye-bye,” recalled Cobb.

Instead of just letting the kid treat him this poorly, Cobb spoke with the principal and said that he was planning to talk to this student’s father. Cobb went to the village above the school where the majority of the students lived and found his house. 

He knocked on the door and informed the dad that his son had assaulted him and that Cobb didn’t want it to happen again. The father then took off his belt and moved to beat his son, but Cobb told him, “No, I don’t want that to happen. I’m a nice guy, but I just want to make it clear, if he ever does that again to me, he will get charged for assault in the first degree.”

The father, who Cobb thought was pretty cool, ended up inviting him to stay for dinner, and the kid who threw him out the window had to serve him and help him with anything, therefore helping to teach him his lesson. 

This was only one of the two crazy adventures that Cobb experienced while teaching in the Virgin Islands, the second involving even more violence and consequence than the first.

One time, a bit later after the window incident, Cobb gave his students a test in Spanish. The kids took the test and for some reason or another, one boy got an F.

Later that day Cobb was heading out wearing steel-toed combat boots because he was about to go help his friend build a house. As he was about to leave, the boy who got an F on the test ran up to him and slashed Cobb’s leg with a jackknife. Then, to defend himself, Cobb kicked the boy in the knee with his boot, which busted the boy’s knee.

“Well, this kid’s father sues me. I said, ‘fine.’ Well, I counter sue. You sue me. I sue you. So he sued me for five grand. So I sue him for five grand. I said, ‘this is a cakewalk. This is a slam dunk. I’m gonna represent myself,’” said Cobb.

After some hard work, Cobb found 80 witnesses, and at his trial, he called the first 10 up to the stand. They all said the same thing, that Cobb kicking the boy was an act of self-defense after the kid slashed him with a blade. 

“The judge goes, ‘how many more witnesses do you have?’ I go, ‘about 70 your Honor.’ He says, ‘you sit down, you proved your case.’”

The judge then turned to the kid and asked why he stabbed Cobb, and the kid’s only response was that it was because Cobb gave him an F on the test. So, Cobb’s hard work paid off and the kid’s dad had to pay Cobb $5,000 dollars. 

After these incidents, Cobb decided that in order to relate to the kids, he would learn how to rap, specifically like Bob Marley.

“I figured if I rapped, because Bob Marley and reggae was a big thing in the Virgin Islands, that I would get more respect, and it did happen,” Cobb said.

And thus, the legend of the rapping sub was born.  

After learning to rap, and teaching in St. Croix for a few more years, he began to think about moving to another city. He didn’t see much of a future for himself in the Virgin Islands and also didn’t like that the islands were so disconnected from the world. Because of this, he decided to move to Portland in June, 1983.

Upon his arrival, he was hired by Portland Public Schools as a substitute teacher. He started out teaching in various grades but eventually came to prefer high school. He turned down a teaching position at Grant due to fears of getting laid off and continued being a substitute.

Despite his love for subbing, Cobb was still interested in a full-time teaching position. In 1991 he took an interview for a job as a Spanish teacher, but he didn’t end up getting it. The woman who got it over him was the woman he would later marry. 

“Won the girl, lost the job,” said Cobb. 

In 1999, Cobb went back to school to work towards a master’s degree in library science. He finished his degree in 2003 and quickly got hired at Cleveland High School due to being a librarian who could speak Spanish. This position began his work at Cleveland, as both a librarian and a substitute.

Cobb has now been subbing for Portland Public Schools for 42 years, with a goal of teaching for 50. He’s a kind and helpful person, and the best sub in the district. 

Cobb says, “I love helping you get to college. I like helping you with assignments. I’m always offering if you have trouble with Spanish which I’ve been taking for 58 years. I’m at your service.”