When a successful 1883 art loan exhibition proved that Detroit was ready for its own museum, leading citizens incorporated the Detroit Museum of Art two years later and began raising funds for a permanent building. Museum trustees selected plans submitted by architect James Balfour of Hamilton, Ontario. Critics said the design was too extravagant, and more suitable for a location with an expansive lawn rather in the heart of a bustling city. But the Norman-style museum was erected anyway, and it was here that early treasures of the Detroit Institute of Arts, including the Van Gogh self-portrait, were originally displayed. 

After the museum relocated to Woodward Avenue in 1927, the old building housed the Detroit Public Welfare Department and the Veterans of Foreign Wars. The former museum saw the wrecking ball in August 1960 to make way for the expressway now designated I-375. But it may end up being all for nothing—city planners now want to return the I-375 right-of-way back into traditional surface streets.

This gorgeous Second Empire building was, in many ways, the center of city life in Detroit for 90 years. Built in 1871, old City Hall hosted major events—parades, festivals, speeches—at its perch next to Campus Martius. The building had a huge clock tower designed by W.A. Hendrie (which he described as his “masterpiece”) and sculptures by Julius Theodore Melchers.

But in the 20th century, the building began to show signs of its age. It didn’t match standards for architecture or safety, and it desperately needed cleaning and updates. Unfortunately, there wasn’t the appetite to make the necessary changes.

After a new City Hall was built (now the Coleman A. Young Municipal Center), the old one’s clock was ticking. It was finally demolished in 1961. One Kennedy Square occupies the site today.

After the city's first opera house was destroyed by fire on the morning of October 7, 1897, its owners rebuilt on the same spot on Campus Martius where the original had opened 28 years earlier. Architects Mason & Rice blended French Renaissance and Corinthian elements in the facade's design. Theater attendance declined as the city's elite moved farther from downtown, and the venue began primarily showing films in 1931. Several proposals for what to do with the dying theater were announced, including a restaurant, an indoor sports center, and a bus station, but all fell through. In December 1935, work began on converting the theater into a second location for Sam's Cut Rate, a drug store that later evolved into a discount department store. 

In 1965, the City of Detroit purchased every lot on this block and leveled it completely the following year in order to attract development. The block remained unoccupied until Compuware's headquarters opened there in 2003, nearly 40 years later.

Alexander Chene built this Federal-style brick home on East Jefferson around 1850. In 1902, millionaire Charles B. Warren purchased, renovated, and added onto the structure. After serving as a University of Detroit fraternity house, it was converted into Little Harry's Restaurant in 1933.

Anita Baker and her husband, Walter Bridgforth Jr., purchased the Chene House in 1990 and announced "exciting plans" for the site. They obtained a demolition permit despite the building's historic designation, but the permit was rescinded once the error was made public. The couple, who bought the property for $575,000, attempted to claim a hardship exemption, but the city's Historic District Commission ordered them to sell the property instead. It was listed for $950,000 and found no buyers. A year later, the demolition request was added to the commission's agenda as a “walk-on item” with no public notice, and approved. Although preservationists won a court-issued stay on the demo on April 5, 1991, a wrecking crew arrived the next day and tore down two-thirds of the building anyway. The ruins were declared a safety hazard and demolition proceeded.

Two years later, an “exciting” development was announced for the site: an International House of Pancakes, which still stands today.

In an odd move for a farmers' insurance and fraternity organization, the Gleaner Clearing House Association moved its headquarters from Cairo, Illinois to Detroit in 1908.  Groundbreaking for the Greek Revival building, the work of architect George L. Harvey, occurred on June 8 of that year. In 1958 the building became Newman Hall, a Roman Catholic social organization for Wayne State University students. It was later used as a medical treatment facility. In 1994, WSU purchased the building and demolished it two years later to create twelve faculty parking spaces. Today the space remains a surface-level parking lot.

As we’ve detailed before, the Hudson's building was constructed in stages between 1889 and 1946. The city acquired the building in 1996 and imploded it two years later against the protests of urbanists, preservationists, and the thousands with cherished memories of the once-elegant department store. The $12 million implosion coated downtown with a layer of dust, and damaged the Detroit People Mover track so severely that the system was completely shut down for two months and not in full operation for a year.

Bedrock Detroit is currently constructing a tower on the site that will be one the city’s tallest skyscrapers. By the time the first tenants move in, the site will have been vacant (except for an underground parking garage) for nearly 35 years.

The Donovan Building Company hired Albert Kahn to design this ten-story retail and office building, which opened in 1923. Most notably, it served as the headquarters of Motown Records, which began moving into the building in December 1967. The dream was short lived, however, and the record company left Detroit for Los Angeles in 1972. 

As late as the early 2000s, urban explorers noted that the building still contained intact architectural details as well as mountains of Mowtown memorabilia. In anticipation of Super Bowl XL, the city pressured the building's owner, Cherry Lawn Realty (partly owned by Berry Gordy Jr.), to tear down the building "for parking." In January 2006, the building where the Jackson 5 auditioned for Berry Gordy Jr. in his eighth-floor office was reduced to rubble. The site remains vacant today.

Perhaps it was bad timing that ultimately did the Lafayette Building in. The neo-classical office building, designed by C. Howard Crane, opened in 1923 but ultimately closed in 1997.  Tenants included the Michigan Supreme Court and Walter's Pipe Shop, which rented space in the building for almost the entirety of its existence, according to Historic Detroit. 

The Downtown Development Authority (DDA) purchased the building from a slumlord owner in 2004 and became determined early on to demolish the structure. Preservationists fought to save the building, but in June 2009 the Detroit City Council voted against historic designation. Three days later, the DDA voted to raze the building. The following month, Quicken Loans announced it was moving to downtown Detroit, eventually spearheading a host of historic office building renovations. But it was too late for the Lafayette—it would be gone in a matter of months. The site is how home to an urban farm and green space.

Celebrated architect Louis Kamper designed this thirteen-story hotel, completed in 1925. Each of its 252 rooms contained a private bath and shower, considered special features for a residential hotel at the time. The Salvation Army purchased the building and used it as a home for the elderly, called Eventide, from 1959 through 1980, and later as a homeless shelter until 2007. 

Two years later, Olympia Entertainment purchased the property through a shadow company, Eventide Properties. Olympia's Little Caesar's Arena, one block over from the Park Avenue Hotel, was designed in such a way so that the historic structure would have to be demolished to make way for the arena's loading dock. Despite the city having previously designated the property a historic site, Detroit's Historic District Commission voted 3-1 to allow the demolition to proceed. It was imploded on July 11, 2015.

Was it the most beautiful or historically significant building? No. Was it the most pointless demolition on this list? Possibly.

Built in 1914, the Smith, Hinchman, and Grylls–designed building housed the Detroit Saturday Night, a newspaper published in the city from 1907 to 1939. Developer Emmett Moten demolished it to make way for a surface parking lot that can accommodate a grand total of 12 cars for residents of luxury condos at the adjacent Fort Shelby. It was last standing structure on the block of Fort Street between 2nd Avenue and 1st Street.