photos/Kiki Garfield
It’s true: the super-rich really are fundamentally different from you and me. Practically a unique species. Possibly alien. They see our world through different kinds of eyes. Their brains are only artificially intelligent. Their hearts are missing.
Tom Landry is a perfect example of this. The slick Portland property broker (Benchmark Real Estate), who also owns a building restoration and construction business (Cornerstone), wrote a column last month for Mainebiz about our state’s residential housing market. Down here in reality, we all know that market is, for all intents and purposes, closed to working people: hopelessly overpriced and under inventory, churning with investment sharks waving checkbooks, the source of an immeasurable amount of anxiety, sadness and suffering [see p. 26 for just the nearest account of this].
Landry’s analysis: “In a word, ‘resilient’ may be the best word to describe the local market,” he wrote. “Impressive” is another bon mot he pulled out, as in, “Some of the numbers are downright impressive, like the median sale price of a single-family home jumping 11.37% and condos an eye-popping 33.2%.”
The disconnect here is plain to see. Humans want homes to live in, maybe raise a family, at least stay out of the rain. Space-leeches like Landry only care about profits for themselves.
One thing I’ve learned after doing this series all these years is that if a property looks dumpy and vacant, chances are high it’s owned by someone with more than enough money to fix it up and provide shelter to someone else. They just don’t, and they can do nothing, for years, because they can afford to pay property taxes on a building that generates no income.
This month’s dump is a four-family building at 108 Washington Ave. in Portland. Inner Washington Avenue has gentrified considerably in the last decade, with hip shops and restaurants and booze tasting rooms lining both sides. But dumps remain, sticking out between the new construction like curiously rotten teeth.
Last month’s junkie deathtrap, at 180 Washington, was bad. This one’s worse: gutted, weed-choked, boarded-up, covered in crappy graffiti and still partially charred from the three-alarm fire that ripped through its upper floor five years ago.
This dump is right next door to the offices for Landry’s real estate and restoration businesses, and an innocent bystander might wonder how in the hell someone who owns a high-end renovation and construction firm is allowing this shithole to rot beside it year after year, sporting a tagged sign that says only parking for Landry’s businesses is allowed in its dirt lot.
Ah, but longtime Bollard readers will remember that Landry is both insufferably smug and deeply dumb.
In early 2013, I wrote about a property Landry was “managing for someone” on the West End, a single-unit apartment building with commercial space on the ground floor, located next to the legendary neighborhood dive bar Popeye’s Ice House (Rest In PBR). Landry repeatedly misrepresented his interest in this property to city officials and concerned neighbors, claiming in public meetings that the building’s poor, naïve landlord had gotten over their head and needed a special zoning exemption to put a snobby restaurant there.
That property was owned by a limited-liability company called, un-ironically, A Better Maine. And for three bucks and an Internet connection to the Maine Secretary of State’s office, anyone could have discovered that the name on that LLC’s paperwork was Amy Landry, devoted wife of the aforementioned space-leech.
Which is to say, Tom owned it, and as I remarked back then, it was “all the more galling … during a time when thousands of renters and homeowners in Portland are struggling to keep a roof over their heads, [that] this yuppie fuck is pretending to represent a cash-strapped landlord — who in reality is himself — to fool neighbors and city officials into waiving the rules for his rich buddy’s vanity project.”
Landry did not respond to questions about his Washington Ave. building last month. I suspect that “yuppie fuck” remark explains why.
Anyway, for his East End dump, which this yuppie fuck bought over six years ago for $760,000, he just called the LLC 108-112 Wash. His is the only name on the state filings, along with the address of the condo he and Amy have on Pine Street in the West End.

Before the big fire, restaurant and retail laborers who worked nearby happily lived there for many years. “From ’11 to ’15 it was a great place!” wrote Danial Deschaine, who rented there while working in the hospitality industry. “Kind of a block party of neighbors who all knew each other and hung out amongst each others’ apartments from time to time…”
What’s the plan for this place now? Sources, including neighbors and industry insiders who spoke off record, said it’s unlikely to become a home for working people again anytime soon. Seems Lyin’ Tom has bigger ideas, a way to make more money.
Once again, city and state records are our friends. They reveal that on July 7, 2022, Landry bought two properties on Winthrop Street, just below his Washington Ave. eyesore: a single-family home and the vacant lot next to it. The unremarkable home sold for the impressive sum of $750,000, and the tiny lot changed hands for the same amount, a truly eye-popping $1.5 million transaction!
Landry (and possibly some investors from a neighboring galaxy) may be waiting to snap up another adjacent parcel or two before announcing a big project on the block. Or waiting for interest rates to go down. Or a message from Betelgeuce to arrive. Who knows? He ain’t talkin’.
Meanwhile, the millions of visitors to this trendy part of town get to gawk at the shithole next to Tom’s offices for another year or two or three… Residents of the distinctly un-yuppified East Bayside neighborhood below get to gaze up at the burnt, graffiti-covered backside of the place for another year through the gap afforded by the vacant lot Tom bought for something like five grand a square foot.
Next time you’re looking for someone to blame for Portland’s dystopian housing market, don’t look at all the homeless or Airbnb people. Stare straight at greedy assholes like Tom Landry, who so obviously care more about growing their fortunes than the misfortunes of everyone else, and let them know exactly what you think.
Kiki Garfield contributed reporting to this article.
