Picture-perfect ending: Beloved Oakland rabbi retiring after 22 years

To help pay for rabbinical school back in the ’60s, a young Steven Chester had to sell all his treasured photographic equipment, putting his hobby on hold.

Soon, he’ll have time to put the darkroom back together. After 40 years in the rabbinate, 22 of them on the bimah of Oakland’s Temple Sinai, Chester officially retires later this month.

Rabbi Steven Chester

But not before his congregants throw him a weekend-long party, including special Shabbat evening and morning services, as well as a dinner and celebration. The love fest begins June 10.

“I’m feeling very excited,” Chester said about the upcoming events. “At the same time I’m so busy with people wanting last-minute appointments, I almost don’t have time to think about it.”

Chester’s tenure at Temple Sinai was a time of growth, both of the downtown Oakland synagogue’s physical plant and of the congregation itself, which now tops 1,000 families.

Based on testimonials of those who know him, Chester will be remembered for his kindness and devotion to his congregation.

“He’s had an immeasurably positive impact on both Temple Sinai and the broader East Bay community,” says congregational president Barry Dubin. “The word is overused, but he’s a mensch, a real down-to-earth person. He respects people. He’s involved.”

Chester’s fellow clergy share the sentiment, including Ilene Keys, who landed the cantor’s post at Temple Sinai straight out of cantorial school 16 years ago. Chester is the only senior rabbi she ever worked with.

Keys credits Chester as the principal reason she wanted to work at Temple Sinai. After her job interview with him at Hebrew Union College in New York, she recalls, he stretched out his hand to signal his approval.

“It was such a touching moment,” she says. “That was what clinched it.  He was so open and down-to-earth, I felt I just had to come. We’ve just had a wonderful relationship for 16 years. We’ve never fought, we’re very respectful of each other’s opinions. He allowed me to grown as a cantor. He’s been a mentor, a teacher and a good friend.

“We are a really good team,” Keys adds. “We’ve always had a very smooth rapport on the bimah. We joke, we can make fun of each other. He makes fun of how he can’t sing, but he does love to sing.

Oakland was the last stop of Chester’s rabbinic career, but not the first. After ordination in 1971, he served smaller congregations in Jackson, Mich., and Stockton, as well as serving as a prison chaplain in Michigan.

When he arrived at Temple Sinai in 1979, his goal was to develop the congregation’s sense of community so that it “became a second home to people,” he says. “We could talk to potential members about the wonderful programs, but bottom line, it had to be a place [where] people felt at home, safe and nurtured. We worked to create that warmth and caring feeling.”

Chester did that by plying the customary rabbi skills, in sermons, during the holidays and lifecycle events. His congregants say there was nothing customary about the Chester style.

“He listens to people,” Dubin says. “I can’t tell you how many times I’ve been to services when his remarks incorporate something someone else has said. He picks up on things and makes you feel appreciated.”

It’s not all about pastoral kindliness. Chester has a sharp sense of humor, something put on display during the synagogue’s annual Purim party.

That’s when the rabbi, dressed in drag and wearing full makeup, assumes the identity of Esther Chester. Friends say he really knows how to rock the frock.

Chester also played a key role in Temple Sinai’s $15 million remodel, which added 18,000 square feet of space to the campus and featured a new chapel,  15 classrooms, a teen lounge and library.

The facility was renamed the Steve and Leona Chester Campus.

“You can’t overstate the role he played,” Dubin says. “That new facility is a tribute to him, and demonstrates the love and respect the congregation has for him, and the many hours he spent working on fundraising.”

“It’s not the building itself — it’s what it represents: to serve the congregation more easily,” Chester says, “and the wonder that a congregation this size had almost 80 percent caring enough to be part of the capital campaign. We raised a goodly amount of money because they cared.”

In addition to the construction project, Chester takes pride in Temple Sinai’s determination to remain an inner city congregation. He also points to the synagogue’s literacy program in the Oakland schools and its annual holiday food drive as examples of members’ commitment to social action.

Chester has no set plans for the first few months of retirement, other than to lay low and allow Temple Sinai’s new senior rabbi, Andrew Straus (formerly of Peninsula Temple Sholom in Burlingame), to settle in.

After that he anticipates pursuing new interests (and old, such as photography) and spending time with family. As for his time at Sinai, he says, “If I had to do it all over again, there would be no question, and do it the same way.”

For information about the gala weekend to honor Rabbi Steven Chester on June 10 and 11, go to www.oaklandsinai.org.

Dan Pine

Dan Pine is a contributing editor at J. He was a longtime staff writer at J. and retired as news editor in 2020.