The Special Election two weeks ago to fill the seat of disgraced County Supervisor Nathan Fletcher has now added a new chapter to what was already one of San Diego's worst political dramas.

San Diego City Councilwoman Monica Montgomery Steppe led three other candidates in the Special Election, but, she still fell short of reaching more than 50% of the vote so a run-off election will be held on November 7th to determine who will serve out the remainder of Fletcher’s term through December 2026.

The election, of course, was the result of Fletcher's resignation in May after a female transit agency employee filed a lawsuit alleging he stalked and assaulted her while he was the transit agency’s chairman.

The Special Election drew four candidates: Montgomery Steppe, a Democrat; Republican Amy Reichert, a local private investigator who lost to Fletcher last November; Democrat Janessa Goldbeck, a former congressional candidate and US Marine Corps officer; and Republican Paul McQuigg, a retired US Marine Corps Gunnery Sergeant who earned a Purple Heart after being injured in a bombing while serving in Iraq.

The district is made up of a majority of registered Democrats, but, in a special election with low voter turnout, the end results were hard to predict.

And given two high-profile Democrats in Goldbeck and Montgomery Steppe, and Reichert backed by her Party, a big political battle was expected.

But what wasn’t expected was how traditional campaign donors and supporters would act in this mad dash to win a special election that will determine the partisan balance of the County Board of Supervisors.

Just weeks before the election, two very similar campaign mailers began landing throughout the district with clear color pictures of Goldbeck, a White woman, and grainy grayscale pictures of Montgomery Steppe, an African-American and the only person of color among the four candidates.

Not only were the mailers seemingly racist, but they also accused Montgomery Steppe of lying to the public about lower homicide rates in her district during her five years in office and suggesting she supports defunding police, clearly a dog whistle to scare White voters away from the Black candidate.

The truth is that the crime stats Monica used were given to her Council office in an email from a SDPD Captain, and that Monica voted for every City budget during her time in office which all included increases to the police department’s budget.

The shocker was that the mailers were paid for by the San Diego Police Officers’ union and the union of County Deputy District Attorneys, the prosecutors in DA Summer Stephan’s office.

The police officers’ and prosecutors’ unions misrepresented -to put it nicely- the facts to voters and accused Monica of lying.

This is the political equivalent of planting evidence and wrongfully prosecuting an innocent person. It was a hit job!

The law enforcement unions have traditionally supported the more conservative candidates and usually run positive campaigns to help elect them by using the imprimatur of the police badge to vouch for candidates’ credibility.

But this use of negative hits deploying tired racial tropes and unfounded claims damaged not only the law enforcement unions’ brands but also tarnished their credibility among the community that must believe police and prosecutors when they say their tactics on the streets are not based on politics or race. They squandered their reputations over a political campaign.

Then after the election, we discovered that developers and conservative business leaders who have traditionally supported Republicans were masking their contributions to Goldbeck, a Democrat, through obscure campaign committees with similar names to make it harder for the public to track the donations.

It was a tactic designed to protect the Democrat from criticism among her Democratic friends for accepting contributions from supporters who are not in line with traditional Democratic policies and positions, including unionization, delivering more affordable housing units, and environmental regulations.

These business interests used to give openly to Republicans when the GOP had majority control of the City Council and County Board, but now that Democrats have total control of the City and could again have majority control of the Board of Supervisors, these special interests have to find ways to disguise their donations through complex and opaque channels and help get the most favorable (to them) Democrats elected while quietly opposing the Republicans they believe can’t win.

One group funded by downtown powerbroker Steve Cushman and other business leaders supporting Goldbeck even spent money to support the lowest-polling candidate, Paul McQuigg, in a desperate effort to pull votes from Republican Reichert and help push Goldbeck into the runoff election.

So what we’re witnessing now is friction between progressive Democrats pushing aggressive policies on housing and criminal justice reform and more moderate Democrats who support the positions of developers, business leaders, and law enforcement unions -and gladly take their contributions in direct and indirect ways.

The break was made clear last week when the YIMBY Democrats of San Diego, a local political group that advocates for housing policies, sent a letter to the San Diego Housing Commission asking for changes to a proposed City housing policy.

The YIMBY (Yes In My BackYard) Dems, who claim that “more new homes of all income types are necessary to achieve affordability” asked the City to remove requirements in the proposal that called for more very low and low-income units, as well as affordable multi-bedroom units, in new developments of five or more units.

They said the quiet part out loud.

These are developer positions that maximize profitability for investors by allowing more units per parcel, but fail to deliver the kinds of affordable units that working families with children -especially in our under-served minority communities- really need to be able to live close to where they work.

The result of this divergence has been Dem on Dem political violence between what used to be friendly politicos on the same team.

We have seen the divisive campaigns waged against Dr. Akilah Weber and  David Alvarez for their Assembly seats, the hits against former Assemblywoman Lori Saldaña when she ran against Councilwoman Dr. Jen Campbell, the attacks on Brian Maienschein by Heather Ferbert, and now these underhanded tactics used against Monica Montgomery Steppe in support of Goldbeck; all Democrats but of differing shades of blue.

We can track the contributions from law enforcement unions, private prison companies, developers, or business groups and see which candidates benefit from their support and advance their policy positions, that’s why they work so hard to hide these contributions.

In the past few years, several Democratic consultants have moved hundreds of thousands of dollars from developers and business interests to support Democratic candidates through obscure committees with Democratic-sounding names, washed funds through various related committees, and even funneling money through the local Democratic Party which is more than happy to take a cut and look the other way without providing public disclosures to reveal their scheme.

And unfortunately, we've seen local Democratic elected officials who endorse these candidates remain silent instead of denouncing the tactics and attacks, all in the name of winning an election even if it causes long-term harm to Democrats and the Party.

We’ve even seen the divide among labor unions where they end up on opposing sides of political campaigns based on their trades or whether they operate in the public or private sectors, as happened where Montgomery Steppe had the San Diego County Labor Council, SEIU, and the Carpenters’ endorsements while the CalState firefighters union and law enforcement unions supported Goldbeck.

In the case of Goldbeck, her political consultant is also the husband of the leader of the Labor Council who endorsed and supported Montgomery Steppe, working directly against his wife’s organization’s endorsed candidate, yet still taking home consulting fees to their shared household.

But where are the repercussions?

What’s the fallout from using divisive tactics and accepting money from their historic rivals in a desperate effort to win and make money?

Democrats who sided with Goldbeck will have some making up to do after last month’s election. Some chose their side based on friendships or history. Some based on policy differences. Some even played two or three sides just to protect themselves.

But the outcome seems not to be what most expected. Some hoped it would be two Democrats so they would win either way. Some hoped Goldbeck would face and beat Reichert and continue the policies championed by Fletcher and his friends.

Instead, the choice is now between Democrat Monica Montgomery Steppe and Republican Amy Reichert, two diametrically opposed candidates.

The outcome will shift the balance of the Board of Supervisors between Democratic or Republican control, determining funding and policy decisions on mental health, housing, homelessness, transportation, and other important issues.

The Democrats who sided against Montgomery Steppe will have to decide if they will rejoin their partisan side for the greater common good to maintain control of the County. I think most will. (For her part, Goldbeck called Montgomery Steppe to concede within days of the election.)

And a lot of business interests will fear losing access to a majority of the Board for the next year and their fears will be that Reichert cannot win based on a simplistic view of the partisan makeup of the district, so their instincts will be to support Montgomery Steppe through the same obscure committees to keep their fingerprints off the scheme.

After 34 years in politics and direct experience in several special elections, I know it’s not an easy call to make. The broad district stretching from Hillcrest and parts of downtown all the way east to Encanto, Spring Valley, and Mt. Helix is diverse in communities and demographics, and a low voter turnout could skew the partisan tilt.

I still give Montgomery Steppe the edge if she plays her cards right and reached out beyond core Democrats, but Reichert could convince Republicans, lots of Independents, and some conservative Democrats to support her in taking back the Board after five years of Nathan Fletcher’s control and deal-making that many opposed as too woke, too progressive, and too partisan.

Democrats may have ruined their long-term chances by overplaying their hands when they perceived their reign in power would never end. They actually committed the same error of hubris that has plagued Republicans for years.

The next two and a half months will be go by quickly. Only one thing is for sure: No one can predict the outcome.

Stay tuned. Stay alert. And stay informed.

Arturo Castañares is the Publisher and Editor-at-Large of La Prensa San Diego. He is the winner of the Ruben Salazar Award for Excellence in Print Journalism, as well as numbers awards for his political and government reporting. Castañares previously served more than 13 years as staff to the California State Legislature, and as a consultant to various political campaign. Castañares also served as Chairman of the San Diego County Democratic Party, as a delegate to the 2000 Democratic National Convention, and as a delegate to 13 California Democratic Party conventions. He can be reached directly at art@laprensasd.com.