While eating a private dinner in front of the ruins of a nearly 2,000-year-old Roman library in Turkey about 20 years ago, Savas Er set in motion a series of deals that would eventually put him in a position to help rebuild Chicago’s most famous — and most beleaguered — retail corridor.
At its best, Chicago’s Magnificent Mile, the city’s equivalent to New York’s Fifth Avenue, is nowhere near as awe-inspiring as the ancient Library of Celsus, where Er and a business partner celebrated their first deal together accompanied by live chamber music.
But both landmarks have undergone cycles of destruction and resurrection. The library, which once stored more than 12,000 scrolls, was burned down by ancient invaders, leaving only the facade standing. The remaining ruins later crumbled in an earthquake but were revitalized in a long-shot effort by archaeologists in the 1970s, forming the tourist site that still stands today.
In Chicago, Magnificent Mile is undergoing its own rebirth. Between 2020 and 2022, scores of retail tenants closed up shop amid a massive drop in foot traffic caused by Covid closures and property damage from racial justice protests that gave potential new tenants cold feet.
The corridor’s vacancy rate skyrocketed from 15 to 34 percent between 2019 and 2023, according to data tracked by retail brokerage Kirsch Agency. Major real estate players fell into distress on landmark retail properties, including Brookfield, which forfeited a vertical mall known as Water Tower Place to avoid a $300 million foreclosure.
In the more than two decades leading up to this period of decay, however, Er had been assembling an unassuming portfolio that gave him the foundation to set his sights on larger deals.
He primarily picked up distressed suburban retail centers, where he led successful turnaround efforts.
After the pandemic, he was looking to expand in the city proper, and he bought a historic 63,000-square-foot retail property in Chicago’s trendy Wicker Park neighborhood for $20 million in 2022.
The start of a buying spree, Er then acquired two major retail properties on Magnificent Mile and a portfolio of smaller retail spaces in upscale Lakeview.
The period presented Er and his firm, North American Real Estate Group, with his equivalent of an archaeological miracle. But lingering distress in the city could stall Er’s progress and keep the Mag Mile from reaching its full potential.
Er, who keeps a low profile, declined to be interviewed.
Building a portfolio
When Er bought his first retail property from Buzz Ruttenberg — founder of development firm Belgravia Group — he invited Ruttenberg to his home country of Turkey to celebrate. As a thank you, Ruttenberg, a Chicago-native and experienced real estate player 30 years his senior, planned the private dinner at the ancient library to cap off the visit, Ruttenberg said.
The trip marked the start of a long business relationship. For nearly two decades, Er and Ruttenberg quietly partnered on about a dozen retail purchases in Chicago and the suburbs.
Until recently, many of Er’s purchases did not reflect the grand start to his career. The deals, mostly distressed purchases, spanned the mundane offerings of suburbia: a toy store, a grocery store and strip malls. The most exciting may have been a Hooters.
After the pandemic decimated downtown Chicago’s office and retail sectors, Er’s slow, methodical approach to distressed investments began to take off. In 2022, he and Ruttenberg made headlines when they purchased the Flat Iron Arts Building, a historic Chicago Art Deco landmark in Wicker Park, for $20 million.
“All of a sudden one or two deals start happening, or they start to see leases happen, and they realize that the pop-up market is going to evaporate, and if they don’t secure a position, then they’re going to be toast.”
And when the pandemic decimated downtown Chicago’s office and retail sectors, Er was primed to pick up the pieces. He bought a retail property at 605 North Michigan for $47 million, a massive 66 percent discount, as well as the retail space at the bottom of the historic Tribune Tower.
But his transition from sleepy suburbia to Chicago’s landmark retail properties didn’t come without risk.
“He started with what we would regard as small and maybe B-minus or C-plus small strip centers very far from anywhere, because they were the only ones you could buy for small money,” Ruttenberg said.
But in the city, “you have to have confidence and the bank book to afford to be wrong,” he added.
The downturn
It may still be too soon to know which distressed buyers were right about Chicago — and who can hold on long enough to find out.
Greg Kirsch, a Mag Mile retail broker and founder of brokerage Kirsch Agency, believes it may take 10 years to get to 2016 vacancy rates.
“I stand by my 2030 recovery prediction,” he said.
In one of the most emblematic foreclosures of the time period, New York-based MetLife took control of the iconic vertical mall Water Tower Place in 2022 after its previous owner, an affiliate of Toronto-based Brookfield Corporation, surrendered the distressed property to its lender rather than face a messy $300 million foreclosure. Brookfield had lost major tenants during the pandemic, including a Foodlife food hall on its mezzanine level and a 324,000-square-foot Macy’s department store.
Distress like this, rippling through Chicago’s urban core, presented an opportunity for Er, whose deals show a migration into the city.
In the years since 2020, he sold at least eight of his suburban properties and two of his urban properties, public records show.
During the same time period, he bought at least 15 properties, eight of which were in the city. His first major purchase was 605 North Michigan, followed shortly after by the Tribune Tower retail space. He then expanded north to the affluent Southport Corridor in Lakeview with a purchase of three single-tenant retail properties.
Er also bought a 90,455-square-foot shopping center in Lakeview and a 69,000-square-foot office building in the Loop with ground floor retail.
But on Mag Mile, the next task was leasing. Tenants generally were hesitant to commit and were holding out for rock-bottom rents, Kirsch said.
“Everybody’s been circling and doing pop-up and temp deals, and they’re waiting and waiting, because they keep getting these really ridiculously good low rents, and then all of a sudden, one or two deals start happening, or they start to see leases happen, and they realize that the pop-up market is going to evaporate, and if they don’t secure a position, then they’re going to be toast,” Kirsch said.
Eventually, Er landed The North Face at 605 North Michigan. That served as a catalyst for other major leases on the corridor, Kirsch said. Last month, Big City Optical signed a lease at the Er’s Tribune Tower space.
“[North American Real Estate Group] landed the plane first and got the best deal,” Kirsch, who arranged The North Face lease, said.
In total, Er has invested in 2 million square feet of retail in Chicago, the suburbs and investments in Turkey. While Er’s star was rising, Mag Mile was making a gradual comeback.
The come up
Retail vacancy on Mag Mile, which rose steadily between 2020 and 2023, growing from 22 percent to nearly 34 percent in just three years, eventually reversed in 2025, ending the year at 28 percent, according to Kirsch Agency.
Notable deals on the street include large-scale experiential retail leases including The Harry Potter shop, the Candy Hall of Fame and a high-end magic parlor known as The Hand and The Eye.
A push for multifamily could fill out the corridor even more. At 500 North Michigan Avenue, Commonwealth Development Partners is pursuing a $90 million office-to-resi conversion expected to yield 320 units.
As institutional investors are hesitant to re-enter the market, now is a time for locals to thrive, Kirsch said.
“I think most of the acquisition activity was locals. Some of the institutions are coming back in, but none of the big ones,” he said.
Joshua Mintzer, founder of local firm Saxony Properties and Mag Mile landlord who landed the Candy Hall of Fame, said that the time for bottom-feeding is over. Recent leases for clothing brands Aritzia, Alo Yoga and Uniqlo are filling out mid-size retail, and experiences are taking the harder-to-fill spaces now that rents have reset.
The total number of trips shoppers made to the corridor neared pre-pandemic levels in 2025, according to the Magnificent Mile Association.
“Yes, Michigan Avenue has had big vacancies, but such a huge chunk of that has really been because of Water Tower Place,” Mintzer said, referring to the foreclosed mall and office tower.
Now, even that property is on the cusp of a turnaround. The real estate investment arm of insurance giant MetLife is putting $170 million into repositioning it, four years after seizing it through a deed in lieu of foreclosure.
The lender-turned-investor plans to convert upper floors of the property into medical office space.
Still, the city is facing its fair share of uncertainties.
Mayor Brandon Johnson, who has been on fragile footing with the real estate community, is weighing a re-election bid in 2027.
A historically slow pipeline of new development is pushing multifamily rents up but stalling growth opportunities.
And record high vacancy among downtown office space refuses to budge. The rate rose for the 15th consecutive quarter in the second quarter of 2026, landing at 28.6 percent, according to CBRE.
Still, Er’s early career prepared him to outlast the rebuilding phase, Ruttenberg said.
“You learn to develop skills as a bottom fisher when you start out that way,” he said.