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The boarded-up Dorchester house looked as bad as it smelled: An overgrown lawn, discarded liquor and beer bottles, and the stench of rotting garbage wafting from an overflowing trash can.

That late September afternoon at 282 Centre St., a faded red ticket clung to the rusted fence, one of 20 city code violations issued in the two years since a local developer bought the place.

The same entrepreneur bought a tiny red house out of foreclosure on the next block for $191,000 during the financial crisis and racked up 13 code violations over the next decade. Now, it’s a newly built, six-unit condominium complex with a Peloton-equipped gym and other high-end touches selling for the combined asking price of $4.2 million.

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The building owner in both cases is Douglas R. George, the developer and landlord whose wife, City Councilor Annissa Essaibi George, is one of two finalists running for mayor. He has been a quietly visible part of her campaign — standing behind her at campaign rallies and in television advertisements.

Douglas George with his wife, Annissa Essaibi George, after she voted in the preliminary election.
Douglas George with his wife, Annissa Essaibi George, after she voted in the preliminary election.John Tlumacki/Globe Staff

He is also an active player on the city real estate scene, but few know the full breadth of George’s property holdings, or how his business dealings with the city could force his wife to act carefully to avoid conflicts of interest, should she be elected mayor.

George and his companies own some 55 properties in Boston with an assessed value of $54 million, according to a Globe analysis of deeds and corporate records. His portfolio has run the full socioeconomic gamut, from million-dollar condominiums and modern apartments geared toward young professionals, to tidy two- and three-family homes that look well maintained from the street. But he also owns tired, multifamily apartment buildings with broken windows and rotted porches, and at least eight vacant lots and abandoned buildings that have drawn the ire of neighbors.

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He has plans pending before the Boston Planning & Development Agency to build a tower as high as 18 stories with 120 residential units in South Boston.

Boston’s zoning code focuses power in City Hall, so developers large and small have to deal with the city all the time. The city also regulates landlords and protects the rights of tenants. The code enforcement police, tax assessor, building officials, and housing inspectors all work for the mayor. And each has tangled with Essaibi George’s husband in recent years.

A Globe analysis found that since 2008, the city has cited George’s properties for more than 550 code violations with fines totaling more than $40,000, according to Boston’s database of code enforcement violations.

The tally included 347 violations with more than $25,000 in fines marked “closed,” which signifies the penalty had been paid, according to the city. Another 205 violations with nearly $15,000 in fines remain “open,” meaning they remain unpaid or under appeal.

George’s properties have been cited 376 times for trash, 98 times for overgrown weeds, and 15 times for failing to shovel snow, according to the data. The tally includes 82 code violations since Councilor Essaibi George launched her campaign for mayor in January.

George’s lawyer initially disputed the accuracy of the city’s record of violations, calling the total grossly exaggerated. After reviewing the Globe’s compilation of public records, attorney David Rich said the city had not properly notified his client of the violations.

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“This is a broken system,” Rich said. “This is not a Douglas George issue, but rather a citywide systemic failure.”

Rich noted that the majority of the violations were for improper trash storage, which he said was the fault of tenants. The city, however, holds property owners responsible for such violations.

Essaibi George’s campaign bridled at the Globe scrutiny of the properties owned and managed by the candidate’s husband.

“The Globe is throwing anything it can at the wall to see what sticks as it relates to Annissa’s husband,” said a statement from campaign spokeswoman Nicole Caravella. “If Annissa’s husband is in violation of any regulation, he will pay, he will be held accountable just like anyone else. She has made it abundantly clear in many interviews her plans to keep that separation between her work and her husband’s.”

Douglas R. George declined an interview request, but issued a five-page letter through his lawyer, alleging that the Globe was seeking to ruin his reputation to aid the campaign of his wife’s political rival, City Councilor Michelle Wu.

“Mr. George has a strong record of creating needed housing in the City of Boston,” the letter read, adding that, “George strongly disputes that his properties are a blight on the community.”

Experts said that while there is nothing unusual or questionable about a municipal official having a spouse who has business interactions with the city, it can be a challenge to make sure that no conflicts of interest arise.

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“It’s a delicate situation for a mayor to [have a] spouse with those kinds of business activities,” said Alan Mallach, a senior fellow at the Center for Community Progress, a national nonprofit working to combat vacant and deteriorated properties. “Because the fact is those are business activities that constantly in one way or another — whether it has to do with code enforcement or zoning or building permits — involve the city.”

Essaibi George has no ownership or management role in any of her husband’s many companies, but state law prohibits any public employee from official involvement in matters in which their spouse has a financial interest.

Essaibi George declined an interview request. In a statement, her campaign said that as mayor her work would remain separate from that of her husband. The campaign also provided a September letter from the state Ethics Commission that outlined how the conflict of interest law would affect her potential mayoral administration.

The advisory noted that when it came to her husband’s businesses, the law bars her from acting in her official capacity in discussions, informal lobbying, offering advice, or even personally delegating matters to aides. Real estate is particularly complex because the conflict of interest law can extend to neighboring properties. The ethics advisory noted that as mayor, Essaibi George should not take any action on matters involving properties abutting or near her husband’s land. The campaign said she intended to follow the advisory.

Erin O’Brien, a political science professor at the University of Massachusetts Boston, said it would be unfair to prohibit political spouses from operating a business. But she said there are, beyond the need to abide by ethics law, practical concerns about how front-line city workers would regulate Douglas George’s properties if Essaibi George wins.

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“As a street-level bureaucrat, do you want to give a major violation to the mayor’s husband? I think most of us would answer no,” said O’Brien.

“If you’re one of the tenants, would you want to complain?” O’Brien said.

Essaibi George has pledged that if she is elected, her husband will not seek city approval for new developments, although he is involved in two projects currently pending before the Boston Planning & Development Agency. The campaign and George did not answer a question about whether he would continue to pursue those developments if she is elected.

Douglas George’s businesses have offered some support for her bid for mayor.

Last month at least 17 of his properties displayed Essaibi George for mayor signs. One stood outside a brick two-family on Saxton Street, where in July city inspectors issued George violations after the bathroom ceiling collapsed.

A house on Saxton Street owned by developer Douglas R. George.
A house on Saxton Street owned by developer Douglas R. George. Erin Clark / Globe Staff

Then there is Columbia Flats, a six-story, 40-unit apartment complex being built by one of George’s limited liability companies on Massachusetts Avenue, blocks from the couple’s home.

An unfinished, ground-floor room in the building is being used as storage space for the Essaibi George campaign. A Globe reporter watched as a flatbed truck from a Hyde Park auto body company double parked out front and a man loaded dozens of campaign signs.

State campaign finance law does not bar businesses from posting political signs but does prohibit campaigns from accepting in-kind donations from businesses and generally requires that market-rate rent be paid for storage space and the use of vehicles.

Essaibi George’s campaign has not disclosed any rent payments to her husband’s companies for the sign storage or paying fees to the tow truck company, which has donated to an independent political committee supporting her candidacy. The campaign and Douglas George did not respond to questions about the storage.

“If a campaign is receiving services from a corporation, that must be disclosed in a timely manner,” said Geoff Foster, executive director of Common Cause Massachusetts. “If they are not, that would raise serious concerns under our campaign finances laws.”

One of Essaibi George’s campaign signs overlooks a forlorn vacant lot on Blue Hill Avenue in Roxbury that her husband has owned since 2013.

A neighbor recalled a rare cleanup of the lot last month just before the preliminary mayoral election. But on the morning of Sept. 28, plenty of trash remained, including heaps of brush, a pile of broken lamps, and an old tire.

“If she’s running for mayor, she should beautify that,” said the neighbor, Marline Arana, 51, whose opinion of Essaibi George was tainted by the condition of her husband’s lot. “Little things like that make a big difference in quality of life.”

 A vacant lot on Blue Hill Avenue owned by developer Douglas George.
A vacant lot on Blue Hill Avenue owned by developer Douglas George. Erin Clark / Globe Staff

Developers sometimes buy vacant lots cheap and let them sit because the land might become more valuable to build on years later. The practice of “land banking” can make sense from a business perspective. But poorly maintained lots can drag down a neighborhood, attracting vandalism and other crime, said Mallach, from the Center for Community Progress, who has studied the impact of vacant properties on cities.

Further north on Blue Hill Avenue, one of George’s companies owns an abandoned house with peeling yellow paint, broken windows, and a roof partially open to the sky. Neighbors consider it an eyesore, and wish he would clean it up and do something with it.

George does generally seek over time to improve properties he owns. He and his companies have constructed a 38-unit building at 35 South Huntington in Mission Hill, which advertises lounges, a gym, and an outdoor deck. He has long bought crumbling buildings or vacant land and built something new.

35 South Huntington Ave. in Boston, owned by a Douglas R. George company.
35 South Huntington Ave. in Boston, owned by a Douglas R. George company.Erin Clark / Globe Staff

Much of his real estate is concentrated in the Polish Triangle section of Dorchester, just south of Andrew Square, where he, his wife, and their children have long lived. Many of his two- and three-family homes there look relatively well maintained.

Those houses stand in contrast to the boarded-up brick building at 15 Medway Street in Lower Mills, which George has owned since 2004. Neighbors said the property is often overgrown with weeds and has been a magnet for graffiti and illicit drinking.

The South Boston site where George has pitched an 18-story tower is currently a shuttered brick warehouse that last month had broken windows and a courtyard piled with old tires, wood pallets, and trash.

The Globe also examined the real estate holdings of the other mayoral finalist, Wu. She and her husband, Conor Pewarski, a commercial real estate banker, own just one piece of property — a two-family house in Roslindale, where they live with their children. Wu’s mother lives in the other unit. There have been no code violations since they bought the house, according to a city spokesman.

Beyond the properties under development, Douglas R. George and his companies own two dozen or more rental properties in Boston with scores of units that require regular interactions with city building and housing inspectors who answer to the mayor. In April, for example, housing inspectors issued George a violation notice for a rat infestation at his worn, three-family building on Esmond Street. Like all violations, it was written on letterhead bearing the mayor’s name.

As a landlord, George has also sometimes clashed with his tenants. Records show he has gone to court at least 20 times in the last decade to evict tenants, including a 2019 case filed against a tenant living in the same building as Essaibi George’s popular Stitch House knitting store on Dorchester Avenue. The company that owns the building and filed for eviction, Stitch House Real Estate LLC, is owned, records show, by George, not his wife.

George’s lawyer did not address the Stitch House case but said eviction is used as a “last resort” for tenants who endanger the safety of others or repeatedly fail to pay rent.

This July, a roof leak collapsed the ceiling in Martha Jackson’s apartment in a building George owns. Jackson said she called one of George’s companies, Polish Triangle Property Management, for two weeks to no avail.

Saying she felt ignored, Jackson, 61, drove to Essaibi George’s campaign headquarters with pictures of the damage. The candidate was not there, she said, but the property management company responded almost immediately.

City inspectors issued George a half-dozen sanitary code violations. Inspectors also cited Jackson for a “severe accumulation of trash and debris,” which George said hampered repair efforts. Jackson acknowledged that her apartment was messy, but said she did not cause the leak in her roof, which city inspections have noted since 2019. George said he responded swiftly to Jackson’s needs and has upheld his obligations as a landlord.

Now back home on Saxton Street, Jackson would like to get rid of the Annissa Essaibi George for mayor sign lashed to the rusted fence outside her building.

“I want to take it down so badly,” Jackson said. “It came from management.”


Andrew Ryan can be reached at andrew.ryan@globe.com Follow him on Twitter @globeandrewryan.