Leaking Roof, Collapsed Ceiling Put Spotlight On Highgrove Holdings

Ishon Arnold speaks to media members in front of his northside home. Photo taken April 16, 2026 by Sophie Bolich.

Northside residents Samantha Gamble and Ishon Arnold have been dealing with a leaky roof at their two-story home for years. Several recent days of pouring rain and high winds have made matters exponentially worse.

Buckets filled with dirty water line the bathroom and bedrooms, furniture is soaked and the second-floor ceiling is caved in. Despite reaching out to landlord David Tomblin and his firm, Highgrove Holdings, Arnold said help hasn’t come.

“Nothing has been fixed at all,” he said. “It’s been raining on my sister’s bed and my mom’s bed — it’s been raining in my room even more. You can even see the ceiling is about to give in in two different areas of the house now.”

The family, who have rented the property at 4425 N. 38th St. for six years, invited media members on a tour of their sodden home Thursday afternoon. In addition to the partially collapsed ceiling and resulting water damage, there is visible mold in several rooms and a hole in the basement heating vent which causes the house’s lower level to become uncomfortably warm.

Arnold said he’s been having to empty some of the containers daily, lugging coolers and buckets down a flight of stairs and out the front door. “That took a lot of work,” he said. “It took a lot of energy out of me — my back was hurting.”

When the family — concerned about severe weather — reached out to Highgrove Holdings on April 14, the firm allegedly said it would send someone the following morning. Nobody showed. “We’ve called them countless times,” Arnold said. “They just gave us nothing.”

In late March, the City of Milwaukee filed a series of lawsuits against Tomblin, targeting the alleged poor condition of more than 200 properties owned by Highgrove and its affiliates. During a press conference at the time, Arnold said his family has been waiting on roof repairs since 2020.

At the same time, Common Ground Southeastern Wisconsin launched an issues campaign focused on Tomblin and Highgrove Holdings, in parallel with the city’s legal action.

“Three weeks ago, Ishon shared his story as publicly as you can possibly get,” said Kevin Solomon, senior associate organizer for Common Ground, during Thursday’s tour. “It’s been 21 days and nothing has been done.”

Highgrove, which is based in California, reportedly owns 263 properties totaling 425 units in Milwaukee, making it one of the three largest out-of-state landlords operating in the city.

Though slow to respond to tenant requests, Solomon said the firm has been distributing a petition in support of Tomblin. According to Solomon, “dozens of tenants” have been asked to sign the document, which allegedly states that “Tomblin doesn’t fix everything, but he tries and he cares.”

“There’s a power dynamic,” Solomon said. “If your landlord shows up and says, ‘I try, I care, sign this please,’ and you’re behind on your rent, or you want things to get fixed, that’s a power dynamic.”

Common Ground and Tenants United said they have arranged for Gamble, Arnold and their immediate family members to stay in a hotel for the weekend. “We’re sending David Tomblin the bill, because this is his mistake,” Solomon said.

After that, Arnold, a member of Tenants United, plans to seek a long-term solution through the nonprofit organization. “We’ve got his back,” Solomon said. “We will find housing if we need to, but ultimately this rests on the landlord. Where’s David Tomblin?”

When asked if he had any hope the home would be fixed under Tomblin, Arnold responded in the negative. “Not at all,” he said. “I doubt he’ll fix this

When reached by phone Thursday, Tomblin referred Urban Milwaukee to a spokesperson through Kane Communications, who shared the following statement on Tomblin’s behalf:

“We are committed to our residents – the people who call our properties home. We’re equally committed to Milwaukee, where we began investing in 2012 and where we have our headquarters. We acknowledge our need to continue to make improvements, and we’re working closely with the City of Milwaukee Department of Neighborhood Services to rehabilitate additional properties throughout the balance of this year.”

Highgrove Holdings is due to appear in court April 27 for an injunction hearing.

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