On a cold February night, about 300 people gathered at a Milwaukee church to relay updates about an out-of-state, neglectful landlord in the city. The raucous crowd settled into expectant silence as Deshawn Harris, one of the landlord’s tenants, walked to the mic.
“Good evening everyone, I’m a tenant of Highgrove Holdings, and I’m with Tenants United,” she began, referencing the growing tenant-rights organization in Milwaukee connected to the nonpartisan community organization Common Ground.
Harris then listed issues she says Highgrove Holdings has not addressed in her duplex, beginning with a bullet that left her living room window broken for five months last summer and fall.
“The bullet is still in my dining room wall,” Harris said. “I have a hole under my front porch that's big enough to bury four or five people up under it. It's been open for six years like that. The backyard looks like a jungle.”
Harris' home is one of over 200 properties owned by Highgrove Holdings Management LLC, a real estate investment company based in Torrance, California. Its founder is David Tomblin, and Tenants United and Common Ground have been organizing with Tomblin’s tenants for about a year to improve conditions. During this time, the group canvassed Highgrove’s properties to document code violations inside homes, and organized tenants to bring their concerns to Tomblin collectively, rather than risk retaliation by going to Tomblin individually.
But Tomblin didn’t respond to their concerns. Now, standing before the crowd of Highgrove tenants and allies in Common Ground, Harris asks for a bold reversal of typical tenant/landlord relations.
“If you think it is time for us to evict David Tomblin, please stand,” she said, to thunderous cheers.
“It’s unanimous,” Harris declared.
But this union of tenants is only one of Tomblin’s problems.
Today, Highgrove's Milwaukee portfolio is in legal trouble. U.S. Bank says Highgrove owes over $8 million after not paying installments on a loan for over a year. It is currently suing Highgrove to place 86 properties into receivership, which would forbid Highgrove from collecting rent on the properties. The City of Milwaukee filed two lawsuits in March that threaten to place an additional 138 properties in receivership, alleging that Highgrove properties legally constitute a “public nuisance.” According to court documents, 37% of Milwaukee properties owned by Highgrove are vacant.
The city’s lawsuits names F Street Investments and Brighton Asset Management as investors in Tomblin’s businesses. Former Milwaukee Bucks co-owner Marc Lasry is listed as an investor in Brighton Asset Management. Through a spokesperson, Lasry declined a request for comment from WUWM.
If the lawsuits are successful, Tomblin and Highgrove will not be able to manage or collect rent from 224 of its properties.
David Tomblin did not agree to an interview with WUWM about the lawsuits or Highgrove’s Milwaukee portfolio.
Over the next three weeks, WUWM will examine how tenants in over 200 Milwaukee properties united to take their landlord to court, and what might happen if they are successful in taking property management out of Highgrove’s hands.
This week, we examine who David Tomblin is, how Highgrove’s Milwaukee portfolio was built, and why Tomblin’s property empire is under threat.
Who is David Tomblin, and what is Highgrove Holdings?
David Lee Tomblin is a California-based investor at the center of a large network of real estate investment companies. He has over five decades investment experience, and founded Highgrove Holdings in 2012 “specifically for acquiring value added distressed real estate within the United States of America for investment purposes.”
Highgrove sits in the middle of Tomblin’s network of investments. Highgrove manages a network of at least 12 LLCs doing business in Milwaukee, but is itself part of the larger Tomblin Asset Management Group, which managed over $1.1 billion in investments, according to Highgrove’s now-defunct investor website.
On the same investor website, Highgrove claimed to be “Woman/Minority owned, Disabled Military Veteran LLC through its managing member TOMCO Equity Management Inc., II.,” as recently as March 2025.
This status would allow Highgrove to claim eligibility for federal contracting privileges. WUWM could not verify who TOMCO Equity Management's leadership is or the claim that it is affiliated with Highgrove or David Tomblin.
But Tomblin has sought special privileges from federal development programs before.
Why Milwaukee?
Tomblin began buying in Milwaukee in 2017, accumulating around 260 properties in just five years. His properties were located primarily on Milwaukee’s north side, often in federally designated “Opportunity Zones.” Created by the 2017 Tax Cuts and Jobs Act, the Opportunity Zone program is meant to incentivize development in “economically distressed” census tracts by offering developers tax incentives.
In Milwaukee, there are over 30 Opportunity Zones, primarily on the city’s north and south sides. Deshawn Harris’ home is in one of these zones.
On his website, Tomblin said as recently as 2025 that Milwaukee had “properties that offer considerable asset appreciation, excellent cash flow above most other areas, and it boasts many ‘friendly-to-landlord’ city policies.”
Tomblin said his Milwaukee homes cost an average of $35,000, including rehabilitation, while receiving a net income of over $6,000 per year. Tomblin promised investors a “12-18%” annual return.
In its complaint, the City of Milwaukee named two investors in Highgrove Holdings: F Street Investments and Brighton Asset Management. Former Milwaukee Bucks co-owner Marc Lasry is listed as an investor in Brighton Asset Management.
John Johnson, research fellow at Marquette University Law School’s Lubar Center, has followed Highgrove Holdings since the company arrived in Milwaukee. Johnson said the benefactors of Highgrove’s strategy of buying cheap housing in Milwaukee’s poorest census tracts were likely a select group of private investors.
“On the early versions of his website you can see he’s suggesting meeting with people of groups of 20 or fewer to pitch them on this investment opportunity, which is to buy cheap houses as rentals in cities that have a lot of cheap housing stock,” Johnson said.
Highgrove moved quickly, often buying homes in batches. Of the over 260 properties it purchased, 135 came from just three bulk deals with other real estate investment companies. Highgrove’s “all cash strategy” allowed it to quickly snap up properties that individual investors or prospective homeowners would never see on the market.
“A common misconception was that these landlords were outcompeting would-be-homebuyers on price, but they were not,” Johnson said. “The advantage that the large investors had is they could go to a local landlord and say ‘I will buy all of your properties in cash.’”
Not the only game in town
Highgrove was not the only investor-backed entity moving into Milwaukee around 2017. At the same time, private equity companies Vinebrook and SFR3 targeted homes, primarily in separate areas of Milwaukee’s north side. Both companies have recently sold much of their Milwaukee properties, with varying profitability; SFR3 doubled its money while Vinebrook took a loss.
Though Highgrove tended to buy the cheapest properties available in Milwaukee, Johnson says the overall strategy of the three companies was similar: buy cheap homes and charge enough in rent to quickly cover the purchase price.
“You get really favorable rent-to-home-value ratios from the perspective of the landlord,” Johnson said. “The math becomes pretty simple at that point.”
Johnson said that Highgrove was similar to these other private equity-backed competitors in that they intended to perfect an investment model in Milwaukee that could be used in other cities. But unlike Vinebrook and SFR3, Highgrove was never able to expand to other cities.
“So they were bringing in these investor dollars, and all three of them planned to operate in multiple cities,” Johnson said. “SFR3 and Vinebrook successfully did that, I think Highgrove ran into so much trouble in Milwaukee that they never expanded beyond that.”
A house of cards comes crashing down
Highgrove bought its last Milwaukee house in 2022, about five years after its first purchase. At the time, Highgrove had about 260 properties in its possession.
To finance these acquisitions, Highgrove took out large loans from investors to purchase and improve homes. According to court documents, Highgrove took out a $6.8 million loan from an affiliate of U.S. Bank. Tomblin bought 86 properties with this loan, but U.S. Bank alleges Highgrove stopped paying installments on the loan in January 2025.
According to court documents, Tomblin said repair costs were higher than expected, citing “COVID-19 and a period of unusually high inflation.” Tomblin’s legal team also noted that 37% of the properties were vacant, restricting expected rental income.
In January, U.S. Bank filed to appoint a receiver for 86 of Tomblin’s properties. Under Wisconsin law, this receiver would be a third-party entity that would manage the property to ensure U.S. Bank receives payments on its loan. If the court approves a receiver, Highgrove would retain legal ownership but would be cut off from rental income from these properties.
This litigation is ongoing. But other Highgrove properties have come under threat of a similar fate, as the City of Milwaukee recently announced two lawsuits looking to appoint a separate receiver for an additional 138 Highgrove properties.
The city’s lawsuit alleges that the 138 properties should be legally categorized as a public nuisance. The city’s complaint cites high vacancy rates, code violations making city government "the effective property manager” and a business practice that is detrimental to the health and wellness of neighbors.
According to the city's complaint, the 138 properties in the city’s lawsuit have generated over 4,000 inspections since 2021. Only 32 permits for repair were filed by Highgrove in that time.
“Highgrove’s lack of proactive inspections or repairs and frequent building code violations require excessive inspections of Defendants’ properties,” the City of Milwaukee alleges in its complaint. This “effectively makes the City a de facto property management service benefitting Defendants at taxpayer expense.”
As of April 6, Highgrove’s LLCs owe at least $303,771 in property taxes to the City of Milwaukee.
Beyond code violations, property taxes, and high vacancy rate, Milwaukee City Attorney Evan Goyke says Highgrove’s business model itself is a nuisance because it prioritizes investor returns over basic repairs.
“They have targeted properties that are distressed [...] and promised investors a rate of return of 10-18%,” Goyke says. “What has not been prioritized is the property’s conditions, building code, property taxes, and those recurring problems that are a public nuisance.”
An alliance to “evict” a landlord
The night Deshawn Harris gave her speech calling to “evict” David Tomblin, Goyke was in attendance. The appearance solidified the city’s partnership with Common Ground, and the mutual interests of the two entities.
“We were aware of who David Tomblin is, the debts he owes and the conditions he has allowed his properties to deteriorate to. What we weren’t aware of, until Tenants United, was the personal human impact that his decisions had,” Goyke told the crowd. “I am committed to working with Common Ground and Tenants United to hold David Tomblin accountable.”
Harris was overjoyed at this alliance, and the momentum she and Common Ground were building. After hugging Goyke and snapping a selfie with him, Harris acknowledged that nothing is guaranteed from the city’s lawsuits. But at least she would no longer have to seek help alone.
“I came a long way from not getting justice to part of justice, you know, seeing it halfway through. That means a lot,” Harris said. “My voice isn’t the only one that’s gonna be heard.”
In future articles, WUWM will dive deeper into the City of Milwaukee’s history of using the receivership law and what to expect from this lawsuit. But next week, we examine how Highgrove’s tenants, like Harris, organized through Common Ground to document code violations hidden from the city and unite to challenge Highgrove collectively.
Support for Seeking Solutions: Keys to Homeownership is provided by Educators Credit Union, Greater Milwaukee Association of Realtors and Geis Garage Doors.
