Feb. 17 2016 12:58 AM

Two Democrats seek to upend GOP city council incumbent

Justin DeCesare
Photo by Ken Stone

In the District 7 race for San Diego City Council, incumbent Scott Sherman has raised four times as much money as his two Democratic rivals combined. The insurance man has GOP support and boasts lifetime friends in the district. He bought and moved back into the same 1,400-square-foot Allied Gardens house he grew up in.

Justin DeCesare, the first challenger to file (in April 2014), has endorsements from Rep. Scott Peters, state Sen. Marty Block, Assemblywoman Lorena Gonzalez and expoliticos Donna Frye and Nathan Fletcher. He’s backed by the League of Conservation Voters and, as of last week, the San Diego Municipal Employees Association. A big get.

Jose Caballero, who filed last May, has Bernie Sanders. Sort of.

Single and 29, Caballero is a former Navy nuclear engineer counting on a political chain reaction to force a November runoff with Sherman, who won election outright in the June 2012 primary by scoring just 53 votes more than the 50 percent needed.

Caballero (part Puerto Rican, Mexican and Spanish) grew up Republican in Texas but says he discovered his true values while studying at San Diego Mesa College (in a class assignment he was startled to hear facts other than those he’d seen on Fox News). Now he’s a full-blown democratic socialist.

District 7—which stretches from Miramar to Mission Valley and includes Tierrasanta and San Carlos—has 72,000 registered voters. Democrats outnumber Republicans 26,000 to 23,000. With a possible X-factor playing into the June 7 primary, Caballero is hoping to leverage his 2,600-member San Diego for Bernie Sanders 2016’s Facebook group and even get the 74-year-old’s endorsement.

“I have a portfolio of what I’ve done” to show Sanders, said Caballero, who also was campaign manager for Kevin Beiser’s successful 2014 school board run. “I’m a proud Candidate for Bernie.”

DeCesare, also a Navy veteran but divulging no White House pick, rolls his eyes.

“The way I’m running my race is not campaigning for a presidential candidate,” he says. “I have a lot more work to do here in District 7.”

Caballero, who raised $20,000 last year and spent almost all of it, said he planned to knock on 100 doors a day starting Feb. 10, handing folks personalized issue letters. He calls residents his consultants—in contrast to DeCesare’s hiring a paid campaign manager (John Parker) and strategy adviser (Tom Shepard).

“Money is just a measure of the old way of politicking, which is throw as much trash in the mailbox as possible, and be able to win over a voter with a fancy, splashy message,” Caballero says.

Jose Caballero
Photo by Ken Stone

DeCesare, 33 in March, says he’ll hit “every door in every precinct as hard as we can, knowing that Scott has enough money to sit back and not actually have to talk to people in the community. And he can send postcards all day long.”

He’ll do this while keeping his day job, managing 35-40 people at his real estate brokerage. DeCesare says he’s the one who fixes the broken office printer. (In 2004, he won a Pacific region award as the Navy’s Air Traffic Control Technician of the Year.)

Both challengers think Sherman is vulnerable—and say a District 1 victory by Barbara Bry could make possible a Democratic six-vote supermajority on the city council.

Sherman, his challengers say, is overly focused on Chargers stadium issues and “big-ticket items that get you on the news,” in the words of DeCesare (pronounced Dee-Caesar, like the salad).

DeCesare, president of the Tierrasanta Community Council and Planning Group, says Sherman isn’t looking out for micro concerns such as a much-wanted dog park or a lost senior center.

But Caballero has an eye on macro prizes as well—including a proposal that could serve as his campaign slogan— “Too Small to Fail.”

A business consultant with a San Diego State University political science degree, the Linda Vista resident has devised a plan for having a $15-an-hour minimum wage without hurting small businesses. He predicts sales-tax revenue would soar, and he’d take a portion of that growth and give it to struggling shops willing to open their books and prove their profit-per-employee is small enough. He’s still working on details.

“You create a cycle that allows the small businesses to catch up to the ($15-an-hour) economy,” he says. “It will be a big impact on Day 1…We can’t allow those big businesses to gobble up our small businesses because they can afford to pay their workers more.”

Scott Sherman
Photo by Chris Stone

DeCesare, an acoustic guitar player, calls for immediate infrastructure spending. He thinks it will be music to D7 ears—especially after El Niño rains flooded San Carlos homes in January.

“Our best way to fix this problem is to first understand that we need to find new revenue that makes the probability of fixing these repairs more likely in the short term, to stop trying to play bait-and-switch with city services to look like a financial savior of the city,” he wrote recently. “It’s time we stop kicking the can down the road.”

The nearly 53-year-old Sherman is undecided on a GOP presidential nominee (“Not totally excited about anyone in particular at this point”). But he pushes back on claims he doesn’t look out for his communities.

“I introduced the Navajo Parks Renovation Plan that improved and updated six District 7 neighborhood parks,” he says. “I worked…to reopen overnight camping at the Kumeyaay Campgrounds in District 7 after being shut down for over three years.”

He says his office won state grants and teamed with Tony Hawk to build a $3 million skate park in Linda Vista, and found money to reopen the Hex Building and install sports field lighting at the Tierrasanta Rec Center “after seven years of residents waiting.”

Sherman, a black belt in Cuong Nhu karaté recovering from bad knees, is a big-time fisherman. He boasts landing a 350-pound marlin. From a kayak, he caught a 42-pound Yellowtail tuna.

Now he’s angling for Democratic votes as well.


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