"I need to get to know people, and I'd ask the same of the community," Winston said in a recent interview with the Weekly.
"There's tremendous tradition at Paly, and I need to understand that for my own well-being.
"My goal is to understand the community, keep it student-centered and maintain the focus that's been achieved over the years."
In his small, tidy office at Gunn, Winston keeps a shelf full of administrative manuals, a whiteboard full of unintelligible scrawls, and a bulletin board containing a color photo from a Milpitas newspaper featuring his two children, Conner, 7, and Meghan, 3, at play.
Adjacent is a tacked-up quotation from 18th century English Parliamentarian and abolitionist Thomas Foxwell Buxton: "With ordinary talent and extraordinary perseverance, all things are attainable."
Talent aside, his perseverance stands out.
Growing up in Milpitas, he worked summers as a gardener and custodian through a city program and graduated from Milpitas High School.
With a four-year college financially out of reach, Winston attended Mission College, working as he studied. He transferred to California State University at Hayward (now Cal State East Bay), where he earned a degree in psychology.
He took classes in marriage and family therapy — an interest at the time — but switched to teaching as he approached graduation.
"I'd always had a real desire and passion for working with people, particularly young adults," he said.
"It wasn't until the end of college when I realized the power of a teacher, and that's when I decided I was going to try to do that."
Winston said he was drawn to special education after witnessing "the power of some good interventions" on a person close to him.
He found a program at Santa Clara University that allowed him to do supervised, paid internships while earning a teaching credential. He did his student teaching in his hometown of Milpitas.
"I worked to pay my way through school, and it changes the value of education when you're able to do that," he said.
"You value the product, and the product is the work you put into it.
"I went into junior college (Mission) very focused, with my mind set on where I was going to go. I took advantage of the great price that was there, and got in and out as quickly as I could."
Winston taught special education for six years in Milpitas and for a year at JLS Middle School.
"A piece of my heart" always will remain in special ed, he said.
But after just a year in Palo Alto, Winston was promoted to become dean of students at Gunn.
"I thought it was a perfect opportunity for my skill set, an opportunity to deal with a larger group of students with a more diverse base," he said of his move into administration.
Asked to elaborate on his skill set, Winston said, "I'm a great listener, a good problem solver and I enjoy shared decision-making. And I do a good job of keeping things student-centered."
"Student-centered" means "continuing to process decisions and how the school functions based on what is best for our students in all areas — academics, student life, culture, social, emotional, guidance, support and extracurricular activities," he said.
"It also means supporting teachers and support staff in every way so they can continue to do exceptional work on our students' behalf."
Winston declined to comment on the "egg wars," an October 2009 egg fight among Paly students that occurred on the Gunn campus, damaging athletic facilities there.
In response, Paly Principal Jacquie McEvoy issued suspensions, many of which later were rescinded. The incident led to some parents openly protesting McEvoy's discipline style. It was one of several situations that created a prickly relationship with students and faculty, although she is credited with spearheading an effective campus-planning process for future improvements. She had strong defenders as well as critics among parents.
McEvoy announced in January she would resign June 30, "with a bittersweet heart," she said in a message to the school community.
Winston did not answer directly when asked about unconfirmed reports on the Town Square forum that he has confiscated student cell phones to view call records.
"I can tell you with 100 percent certainty that everything we do is based on student health and safety," he said. "If it has to do with health and safety then we will do that.
"Sometimes what students see as an invasion of their privacy is really in their best interests."
Winston typically begins his days with a jog around his neighborhood in Milpitas, where he lives with his wife, Anna, a third-grade teacher in the Milpitas school district, and their two children.
The couple met as juniors in a Milpitas High School Spanish class that, coincidentally, was taught by Janet Urbina — now a teacher at Paly.
Winston's mother-in-law, Marsha Grilli, currently chairs the board of the Milpitas Unified School District.
Having worked closely at Gunn with Gunn's newly named principal, Katya Villalobos, Winston said he hopes for more collaboration between the two high schools in the future.
"We're a unified school district, and this is a wonderful time in the history of Palo Alto to enhance our collaborative work," he said.
"Katya is easy to work with and I think we're going to do good work for both schools. I'm not exactly sure how or why, but it's exciting."
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