For most of the past four decades most national retail chains and New York financiers alike had essentially redlined New Haven.

The city’s “reputation” for failed policies and struggling business climate was widely accepted and no major developments or office buildings were built that were not financed by well heeled local developers such as David Chase (Connecticut Financial Center) and David Beckerman (One Audubon Street).

Downtown merchants can remember when the Gap fled one of New Haven’s most visible retail locations (intersection of Chapel and College streets) in 2003. They were followed by Talbot’s, which lasted a bit longer but eventually left, too.

The defections created an impression that New Haven’s downtown wasn’t hospitable to national retailers.

But the city’s retail landscape began to improve and Yale’s University Properties (with 85 retail locations) became more aggressive and now that picture has changed in a big way — likely both helping and hurting local retailers and restaurants.

Apple, perhaps the world’s most desirable retail brand, opened in September 2011 on Broadway. The Urban Outfitters was already open for business in newly re-developed high profile space on Broadway, and along with J. Crew another national fan favorite resides next to the Barnes & Noble Bookstore. Together this fearsome foursome helped turn around the national retail in New Haven failure story.

Today several national retailers have discovered New Haven and not all have been brought to Yale University Properties. Chipotle opened in 2013 in what had been the local restaurant Café Bottega (and an earlier failed attempt at resurrecting the Yale Co-Op) in the Chapel Square Mall at Temple and Church streets.

The ever-so-hip Shake Shack brought its burgers to the home of the birth of the burger (talk about an interloper) in a Yale storefront in 2012, and shopping-center favorite Panera Bread found its way to Chapel Street as well.

All three chains appear to be doing very well, while many of New Haven’s restaurants are operating under increasing pressure for business and as we see a steady flow of restaurant failures and replacements in New Haven.

Even lower Chapel Street — a neighborhood once thought to be impossible to attract national tenants — has two new arrivals.

The really hip (they just opened in Park Slope, Brooklyn — what else do you need to know?) employee-owned 23-store Portland, Me.-based, regional chain Artist & Craftsman at 813-817 Chapel Street is opening this fall in a 6,000-square-foot retail location half a block from the New Haven Green.

The building is owned by Pike International, New Haven’s largest residential landlord. Pike is renovating the upper floors for apartments.

Several blocks up Chapel Street across from the Yale School of Architecture is New Haven’s longtime go-to art store, Hull’s Arts Supply, which will now be duking it out with a much larger competitor.

The cachet of Dollar Tree, the store that sells most everything for $1, is nothing to write home about, but now occupies “prime” space in downtown New Haven.

Dollar Tree has located in the seemingly un-rentable 9,000-square-foot space of C.A. White’s CenterPointe residential and retail development at the corner of Church and Chapel.

CenterPointe apartments filled almost immediately more than a decade ago but the large un-modifiable retail footprint was apparently too much for New Haven’s retail base and the space has stayed vacant.

According to the New Haven Independent, Matthew Nemerson, the city’s economic development administrator, tried to convince C.A. White CEO Michael Schaffer to hold out for a tenant more in keeping with a “hipper” version of downtown. But after ten years Schaffer decided it was time to shake the dollar tree.

The story won’t end there, however. Just a bit down the street at 760 Chapel Street is another dollar store, Family Dollar. The two parent companies just began merger talks with Dollar Tree offering $ 9 billion for Family Dollar creating an $18 billion dollar-store behemoth. Among the issues for the companies and the Federal Trade Commission: overlapping retail outlets.

Even as the dollars started to flow for C.A. White just next door to Dollar Tree, Citibank proved they weren’t too big to fail when in March they stole out of New Haven seemingly in the dark of night. 

Don’t be surprised to see another bank fill the space, however.

Kiko Milano, a cosmetic brand from Italy, and Emporium DNA, a high-end fashion retailer, will open soon at Broadway and York streets. In a surprising turn, both European retailers are using New Haven as a sort of retail beachhead rather than another add-on. Emporium has only four U.S. locations and Kiko Milano three, the closest of each located in New Jersey.