Walk the 3600 block of North Sheffield this month and you'll find a cleared lot where three century-old buildings used to stand. No cranes yet, just chain-link fencing around a lot with a foundation permit that's been on file with the city since January. If you've lived in Wrigleyville for more than a decade, you probably knew these buildings before they were rubble. One of them wore a Latin sign for twenty years that translated, roughly, to "Let's go Cubs." Another was known simply as the Torco Building. Both are gone now, along with a third at 3627 North Sheffield that took until this past spring to finish coming down.
The easy explanation for why they're gone is the one everyone reaches for first: a developer wanted the land, the city said yes, the neighborhood lost a piece of its character. That's the story you've probably already read somewhere else. It's also incomplete. The real reason these three buildings stopped being viable as rooftop businesses has nothing to do with 2024 zoning votes. It happened in 2015, when the Cubs installed a video scoreboard in right field that blocked the exact sightline that had made these roofs valuable since Wrigley Field opened in 1914.
Everything that's happened since, the demolition, the ongoing federal lawsuit against one of the last independent holdouts, the new advertising signs the Cubs got approved this past June, is downstream of that one construction decision. The rooftops didn't lose an argument about neighborhood character. They lost a view.
The Deal That Turned Apartments Into Businesses
For most of Wrigley Field's history, watching a game from a Waveland or Sheffield rooftop was an informal perk of living there, a few folding chairs on a flat roof. That changed once the Cubs became a bigger draw in the 1980s and building owners started charging admission. By 2002 the team sued a handful of rooftop operators for copyright infringement, arguing that selling seats with a view into the ballpark amounted to selling the Cubs' product without paying for it.
The dispute settled in 2004. Eleven of thirteen rooftop operators agreed to hand over 17 percent of gross revenue in exchange for the Cubs' official blessing through 2023. That agreement is what converted these buildings from residential walkups into commercial operations. By 2014, fifteen buildings around the ballpark had made that transition, some with multi-level decks, bars, and full food service built onto what used to be somebody's roof.
The revenue-share deal worked, for a while, because both sides had something to protect. The rooftops had a product only Wrigley Field's open-air design made possible. The Cubs had a cut of money they otherwise wouldn't see. Neither side anticipated what the team's next stadium renovation would do to that arrangement.
What the 2015 Video Board Actually Took Away
The Cubs' $575 million renovation of Wrigley Field, approved by City Council in 2013, added a video scoreboard in right field and a jumbotron in left. For fans inside the park, it modernized a hundred-year-old stadium. For rooftop operators on the Sheffield side, it did something else entirely: it physically blocked the sightline into the field that their entire business depended on.
Alderman Bennett Lawson, whose 44th Ward includes this stretch of Sheffield, put it plainly when the three-building demolition first came before the city:
"Twenty years ago, a lot of these property owners signed a deal with the Cubs to share revenue in order to get their view. And then 10 years ago, the Cubs changed the deal with the city and blocked their view. Many of them sold to the Cubs, and then you have these guys who had nothing as part of the commercial side."
That's the mechanism in one sentence. The buildings that eventually sold to the Ricketts family at least got paid for an asset the family wanted anyway. The buildings that didn't sell, including the trio at 3627, 3631, and 3633 North Sheffield, were left holding rooftop decks with nothing left to look at. Seats that once sold for game-day tickets sat empty for the better part of a decade.
The Trio That's Becoming Apartments
The ownership group behind those three buildings, led by rooftop property investor Marc Anguiano, spent years trying to make the math work before settling on a different use entirely. In 2024, Chicago's City Council approved rezoning the parcels for a single five-story, 29-unit apartment building designed by DXU Architect, with six affordable units, 11 parking spaces along the alley, 21 bike spaces, and two rooftop pickleball courts replacing the old bleacher seating.
A longtime Wrigleyville resident named Lisa Sorenson, who owns property a block away, organized a Change.org petition asking the city to landmark the buildings instead of approving the teardown. It eventually collected roughly 2,900 signatures, and Sorenson argued during the zoning hearing that most neighbors had no idea the project was even under review. The petition didn't change the outcome. The Committee on Zoning, Landmarks and Building Standards approved the plan in June 2024, and the full Council signed off the following month.
Demolition moved in stages rather than all at once. Here's how the timeline actually played out:
| Date | Event |
|---|---|
| June-July 2024 | City Council approves rezoning for 29-unit apartment building |
| Feb.-Aug. 2025 | Demolition permits issued for all three addresses |
| March 2025 | Demolition begins at 3631 (the Torco Building), weeks before the Cubs' home opener |
| January 2026 | Foundation permit for the combined 3627-3633 site posted to the city's data portal; rooftop structures removed from 3627, but demolition there stalls |
| May 2026 | Demolition resumes and completes at 3627, the last of the three lots |
As of this fall, the site sits cleared and permitted, with construction on the apartment building expected to follow the foundation permit issued in January. No completion date has been made public yet.
The One Rooftop Still Fighting in Federal Court
Not every rooftop operator sold to the Ricketts family, and not every one is going quietly. Wrigley View Rooftop, owned by Aidan Dunican, is one of the few independent operators left standing, and the Cubs sued the business in 2024 for misappropriation, trademark infringement, false advertising, and unjust enrichment. The case is still active in front of U.S. District Judge Sharon Johnson Coleman.
Coleman has already ruled that the Cubs' underlying claim is plausible: that the team holds a property right in the product of a live Cubs game, and that selling tickets to watch that game from a neighboring rooftop without paying for it infringes on that right. She leaned on a 1938 precedent involving the Pittsburgh Pirates and a radio station that had stationed observers on a rooftop next to Forbes Field to call games without a broadcast deal. Both sides are now arguing cross motions for summary judgment. The Cubs' reply brief was due Aug. 10, and as of this writing no trial date has been set. The case could still end in settlement, potentially reviving something close to the 2004-2023 revenue-share structure that lapsed once the original agreement expired.
Wrigley View Rooftop's counterargument is straightforward: nothing in Chicago's own municipal code, which explicitly contemplates rooftop seating near Wrigley Field as a lawful activity, supports the idea that a baseball team can claim a property right over what's visible from a neighbor's roof. Until an injunction says otherwise, the business keeps selling tickets.
Why the Cubs Just Added Three More Signs
While one rooftop fight plays out in federal court, the Ricketts family is still expanding its footprint through more conventional means. In June 2026, City Council approved a Cubs-backed plan to add three new advertising signs on buildings the team already owns overlooking the park: one up to 69 feet tall on North Sheffield Avenue, and two smaller signs on West Waveland Avenue rooftops. Wrigley Field's own landmark status limits how much advertising can go up inside the historic ballpark, which makes these rooftop-adjacent buildings, the same ones that used to sell views into the field, valuable now for a completely different reason: they can carry the ads the stadium itself can't.
It's a tidy bookend to the story. The buildings that couldn't survive as ticket-sellers after 2015 are finding new value either as apartments or as billboard real estate for the team that changed their business model in the first place.
What This Means for the Block
None of this is really about nostalgia versus development, even though that's the frame the petition and the news coverage understandably reached for. It's about what happens to a business built entirely around one sightline once that sightline disappears. The buildings that sold their view to the Cubs got paid. The buildings that didn't are either becoming apartments or spending 2026 in federal court arguing about whether a view from private property can belong to somebody else. Both outcomes trace back to a scoreboard installed a decade ago, not to anything a zoning committee decided last year.
If you're watching this corner of Wrigleyville change and wondering what comes next, that's exactly the kind of local shift The VC Team tracks block by block, not just for what it means today but for what it signals about where the neighborhood is headed. Start Your Real Estate Journey with a team that already knows the story behind the story.
