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NewsCommunityMHS Assistant Principal Cheryl Rivera retires after serving MUSD for 33 years

MHS Assistant Principal Cheryl Rivera retires after serving MUSD for 33 years

It was 22 years ago when Cheryl Rivera first began serving as an Assistant Principal at Milpitas High School (MHS). 

This past June, Rivera retired, leaving behind a legacy based in equity and a deep passion for education. 

“I miss the kids,” said Rivera in an interview with The Beat. “I just loved being there for them.” 

Before starting at MHS, Rivera worked for the Milpitas Unified School District (MUSD) in Adult Education, and spent time working with men and women at the Elmwood Main Jail, doing GED and high school diploma classes. She even taught night classes for some time.  

“I started as a teacher, then became a supervisor of other teachers,” said Rivera.

MUSD had a partnership with San Francisco, and would also send some teachers out there to the downtown jail, as well as one in San Bruno. So Rivera had an opportunity to work out there, as well

“It was a fulfilling, eye-opening job,” shared Rivera. 

She recalled how, as a teacher, she would teach the inmates vocabulary words that even the deputies might not know. This made the deputies upset at times; they would ask her, “Why would you teach them all this?” 

Rivera always had the same reply: “They’re intelligent people.” 

“It was a powerful experience for me, working with them,” added Rivera. “It humbled me.” 

After some time, Rivera realized that she had a desire to work with kids — before they got into situations that might lead them to jail. 

That’s what propelled her to look toward MHS for her next job opportunity. 

When she first got there, she taught a year of English. After that, she became an Assistant Principal — and never looked back… 

“I made sure that the students were treated with respect,” said Rivera. “I think that for me, equity is number one. It’s the highest thing on my list. A lot of times, there’s no equity.” 


On a field trip with students to see a play sponsored by SCCABE. Rivera is third from left.


Rivera, who is both of African Ancestry and Caribbean descent, grew up in the Bronx, where the lack of equity was something she lived firsthand. 

Rivera made it her mission to ensure that all students felt valued and welcomed no matter who they were: a minority, someone for whom English was a second language, a student facing learning challenges, and so on.

Jennifer Hutchison, an Assistant Principal at MHS, has known Rivera for the past two decades, and had worked closely with her for the last six years. 

“She is an incredible human who is passionate about equity, education, and served not only students, but their families as well. She is a role model and exceptional example for MUSD staff to learn from,” shared Hutchison with The Beat. 

MUSD’s Director of Human Relations, Damon James, feels that Rivera is a person who has always shared her wisdom, and leads with her heart and soul.  

Cheryl has always been proactive about supporting students in need. I recall her hearing something that did not have an equity lens and saying, ‘That is unacceptable!’” said James.  “Her passion was always met with a willingness to do the work to make things better.”  

MUSD Superintendent Cheryl Jordan told The Beat that she admired Rivera’s humility and spirit-filled wisdom. “Cheryl is a tenacious champion for youth, and she inspires relentless action in assuring they have a learning environment that is free from bias and grounded in respect and appreciation for all,” said Jordan. 

In 2013, Rivera received the Hank Hutchins Award from the Santa Clara County Alliance of Black Educators (SCCABE) for positively affecting the education of African Ancestry students. Then, in 2014, Rivera received an Administrator of the Year Award for Valuing Diversity from the Association of California School Administrators (ACSA).   

After dedicating 33 years to MUSD, Rivera plans on taking some time to write during her retirement. She has ideas for children’s books and other writing projects that she’d like to get moving on. 

Rivera is also spending time taking care of her mother, who is 92 and has dementia. To her, family is the most important thing, so she’s grateful that she can devote ample time to being there for her mom. 

Looking back at her three-decade-plus career at MUSD, Rivera feels grateful for just having been a part of it all. She also spoke of how three of her students went on to become teachers:

“The fact that they wanted to come back and teach where they graduated from, that says something about the school,” Rivera said.   

She also shared that one of the most important things that she did during her time at MHS was listen to the students and show them how much they were valued. 

“I miss that,” said Rivera. “That was the most powerful piece of everything I did, culturally and socially.”  



Rhoda Shapiro
Rhoda Shapiro
Rhoda Shapiro is the winner of a 2022 Golden Quill Award for her Education journalism. She works as a journalist and media consultant in the Bay Area. She has written for both the Tri-City Voice and the Mercury News, and is the founder of Chi Media Company, which works mostly with nonprofit organizations and educational entities to elevate their marketing and communication platforms. Rhoda is also the author of “Fierce Woman: Wake up your Badass Self” and “Magic Within: Womb-Centered Wisdom to Realize the Power of Your Sacred Feminine Self.” Her YouTube channel features practices in yoga, meditation, and women’s empowerment. Rhoda is The Milpitas Beat’s Founder and Editor-in-Chief.


  1. Thank you for honoring Cheryl and her years of service to the Milpitas community!
    Congratulations on a well deserved retirement.


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