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Tom Shepard has been a player in San Diego politics for decades, but he still hasn’t seen it all.

Why this matters

Many different sources of money can back a politician’s run for office. By knowing where that money is coming from, voters can learn about the priorities and connections of candidates on the ballot.

Shepard ran campaigns for four San Diego mayors — Roger Hedgecock, Susan Golding, Jerry Sanders and Bob Filner — and helped elect four of the five current county supervisors on the all-Republican board: Dianne Jacob, Greg Cox, Bill Horn and Ron Roberts.

But this is Roberts’ last term in office after serving for more than two decades, and the county has shifted dramatically over those years. His district, which covers central San Diego, was once dominated by Republicans. Now only 20 percent of the district’s voters are Republicans and 44 percent are Democrats.

The Republicans want to find a way to keep that seat. The Democrats see it as an opportunity to finally wrest the seat from the hands of the GOP.

The high stakes were evident in the June primary, when outside groups spent about $1.2 million to influence the race’s outcome. And the five candidates competing for the November runoff spent another $1.4 million. Finishing first was Democrat Nathan Fletcher, a former assemblyman, and Republican Bonnie Dumanis, a former district attorney.

“I think it’s somewhat unprecedented the amount of independent expenditures that were undertaken in that district,” said Shepard, who isn’t running any of the campaigns for this seat. “I’ve been doing these races since the early ‘90s, and I haven’t ever seen anything quite like that.”

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inewsource has been tracking the money in the District 4 supervisor race. Now that the primary is over, inewsource interviewed people connected to the candidates and others to find out what all of this spending might mean for the November general election.

This is what Shepard said of the Fletcher-Dumanis contest: “If they want to win, they’re going to have to spend a lot of money.”

Saldaña splits the spending

Conservative groups including the Lincoln Club, which have long financed Republican campaigns in the county, knew who to throw their money behind from the beginning. Dumanis was the only Republican on the ticket.

But the county’s labor unions, which are major fundraisers for the Democrats, didn’t agree on who to support. Two Democrats in the primary, Fletcher and Lori Saldaña, are both former state Assembly members, failed mayoral candidates and politicians with name recognition. Fletcher’s wife is Lorena Gonzalez Fletcher, a San Diego assemblywoman and former labor leader.

The rivalry between San Diego’s labor unions has been an undercurrent throughout the race since Fletcher decided to run last year. In December, his wife denounced labor leader Mickey Kasparian and called on him to resign from the county Democratic Party because of sexual harassment lawsuits he was battling in court. In January, Fletcher also called on Kasparian to resign.

Former state Assemblyman Nathan Fletcher is shown here after the primary election on June 5, 2018, at Golden Hall in San Diego. (Megan Wood/inewsource)

Kasparian used to head the San Diego and Imperial Counties Labor Council, an umbrella organization for the county’s labor unions. It’s also the union Gonzalez Fletcher used to head. After facing accusations of sexual harassment and discrimination, Kasparian stepped down from that post and started a new coalition that took eight unions from the Labor Council with it.

A pro-Saldaña PAC that supported her in the primary was sponsored by Kasparian’s new coalition, the San Diego Working Families Council. It spent about $208,000 supporting Saldaña and another $137,000 opposing Fletcher through commercials, fliers and emails.

The other labor union-backed PAC, San Diegans Opposed to Hypocrisy & Lori Saldaña for Supervisor 2018, spent even more than that: $281,000 opposing Saldaña and almost $92,000 supporting Fletcher.

The anti-Saldaña PAC is funded by many of the county’s labor unions that didn’t join Kasparian’s group. The PAC raised at least $170,000 in the last two weeks of the primary alone from unions, including the United Domestic Workers of America, Plumbers Steamfitters & Refrigeration Fitters and the Building Trades Council.

It has also gotten money from the Service Employees International Union, the largest union representing county workers. SEIU originally joined Kasparian’s Working Families Council but split off after the council backed Saldaña for supervisor.

Fletcher adviser Dan Rottenstreich said the campaign was pleased that even with the negative spending, Fletcher captured 29 percent of the vote in the five-candidate primary and finished ahead of Dumanis.

“The primary spending against Fletcher was unprecedented, and Nathan’s ability to beat back those attacks and prevail with a strong, first-place finish is remarkable,” Rottenstreich said. “It puts him in a strong position heading into the general election.”

Rachel Laing, a coordinator for the anti-Saldaña PAC, said the group hasn’t decided whether to continue to put money behind supporting Fletcher in the general election. The Working Families Council did not respond to requests to discuss their plans for the fall.

An uphill battle

The final weeks before the primary marked a shift in strategy for the anti-Saldaña PAC, which had previously spent its money on negative ads targeting Saldaña. On June 1, the PAC spent almost $92,000 on pro-Fletcher TV ads.

Laing said it was a response to the onslaught of negative Fletcher ads coming from the Lincoln Club

“It wasn’t done in a vacuum,” she said. “During the previous (campaign reporting) period, there was a lot of Nathan Fletcher negative spending by the Lincoln Club, and the obvious strategy was that they were spending against Nathan Fletcher because he was the most likely candidate to be able to get through over Lori Saldaña.”

Two PACs sponsored by the Lincoln Club spent no money on independent expenditures to support Dumanis but spent $447,000 on anti-Fletcher ads. More than half of that — $275,400 — was spent in the two weeks before the primary.

Former San Diego County District Attorney Bonnie Dumanis talks with supporters at Golden Hall following the primary election on June 5, 2018. (Megan Wood/inewsource)

But Fletcher also had more money at his disposal than the other candidates. He spent nearly $657,400 in campaign money during the primary, while Dumanis spent about $360,500 and Saldaña spent $41,200. (Democrat Omar Passons spent $345,200 and Democrat Ken Malbrough spent $20,800.)

The San Diego County Democratic Party pitched in, too. It spent about $493,000 supporting Fletcher, while the Republican Party spent $83,000 on Dumanis.

“I think it is going to be a much more aggressive campaign for November,” said Dumanis’ campaign manager, Jason Roe. “We were pretty certain throughout the primary that Bonnie was going to be in the runoff, and we ran a campaign designed to be in the runoff and hold our resources with a focus in November.”

Dumanis might need those resources: She captured 26 percent of the vote in the primary, and the remaining 74 percent went to the four Democrats.

Shepard said both candidates have work to do to win the coveted District 4 supervisor’s seat, but Dumanis might have the tougher job.

“What Nathan has to do is just convince those voters who chose other Democratic candidates that he’s the legitimate Democratic choice in this race,” said Shepard, who handled Fletcher’s failed mayoral bid in 2012. “Whereas Dumanis has got to figure out some way, without emphasizing her partisan affiliation, that she is the preferred choice for some Democrats and many no-party-preference voters. So she’s got a much steeper hill to climb, I think, than he does.”

We’ll let you know when big things happen.

Jill Castellano is an investigative data reporter for inewsource. When she's not deep in a spreadsheet or holed up reporting and writing her next story, she's probably hiking, running or rock climbing. She also loves playing board games and discussing the latest chapters with her book club. Jill...