The Hilsendegen Block was once a staple on Monroe Avenue at Randolph Street for over 70 years, and housed everything from shops to factories, and everything in between. At the time of its construction, it was said to be one of the largest and best business blocks in Detroit.
The building was owned by Valentine Hilsendegen, who was born in Bavaria, Germany, and immigrated to Detroit at a young age. He started off in the wagon and carriage business before becoming a contractor, during which time he accumulated a sizable amount of property.
The Hilsendegen Block was built in two separate phases, with the original part built in the latter half of 1867, which stretched 61 feet along Monroe Avenue, and 109 feet on Randolph Street. The building was under construction by late 1867, and at a point where “it has reached the stage of progress that will easily enable one to judge of its general characteristics,” the Detroit Free Press wrote Nov. 26, 1897. The building was built at a cost of $29,000, or about $1.2 million in 2025, when adjusted for inflation. The basement level was expected to house restaurants. Two of the first-floor storefronts were already rented out before the building was completed. The second floor was used for offices, which were described as roomy and well-lit. The third and fourth floors held halls and meeting places.
The building was designed by the architectural firm of Sheldon Smith & Son, who also designed the first Williams Block Building and the first Detroit Opera House. The masonry was done by William H. Langley, carpentry was done by Henry Hoek, and painting was handled by Drew Harscher.
Some of the earliest tenants of the building included A. Pohl & Co. a cigar and tobacco store, and Huss & Bloom, a dry-goods store, both of which were located there as of 1868., as well as Spahr’s Saloon, located in the basement, which was robbed of 20 bottles of wine, six gallons of liquor, and six boxes of cigars on May 13, 1870, and five more boxes were found tied together, as if it was to be taken but left accidentally, the Detroit Free Press wrote the following morning.
Big plans for a bigger building
Looking to expand the already sizable building, on Jan. 16, 1878, Hilsendegen bought the lot next door, which was home to St. John's German Evangelical Church, out of foreclosure for $22,025 (about $748,000 in 2025). After fighting with the owner of the church for a month, Hilsendegen promptly had it torn down that February to build an addition for the Hilsendegen Block.,
A Detroit Free Press article from March 3, 1878, noted that the addition was to bring the building’s overall dimensions to 120 feet long, 100 feet wide and 60 feet tall, with a dome rising to 80 feet. This addition to the building more than doubled the size of the building, which now took up the entire triangle-shaped block and added three more ground-floor storefronts, for a total of five along Monroe. The work was estimated to cost $40,000 (about $1.4 million in 2025) and start in three weeks and be finished by that July,. The addition was designed by Peter Dederichs, a Detroit architect who designed a number of churches in the city. This would be the last major project Hilsendegen completed in his lifetime.
It appears that the Randolph side of the building also had an addition built at this time, bringing the building in line with Randolph Street. McLennan & Co. drygoods was open in the new section of the building by 1878. The Market Bank moved into the new Randolph corner storefront sometime that same year. The Boston Dry Goods Store opened in the new Monroe-fronting addition at Farrar (later renamed Library Street) on Sept. 4, 1878, however less than a month later, they were bought out by McLennan & Co., which moved out of its store in the second Williams Block Building two blocks over from the Hilsendegen building. Other stores included the Great Bee Hive Store, yet another dry goods store; and Charles Spahr’s saloon.
On Nov. 27, 1881, the Catholic Union Society moved into the Hilsendegen, also from the Williams Block Building. On Nov. 21, 1883, it merged with a second group called the Young Men’s Catholic Association and became the Young Men’s Catholic Union.
According to a Detroit News article from Oct. 22, 1973, the Hilsendegen Building was damaged in the great New Year’s Day fire of 1886, which started in the Ferry Seed Co. Building and wiped out several nearby buildings and caused an estimated $1.5 million in damage. However, articles from the time period suggest that no damage was done to the Hilsendegen Building. The next time there was a fire of this magnitude in Detroit was on Oct. 7, 1897, which saw the destruction of the original Detroit Opera House and surrounding block.
In April 1887, the Executive Board of District Assembly No. 50, Knights of Labor (KOL), leased one of the large halls in the Hilsendegen for three years. The KOL was the first national labor organization in the United States. First starting out as a secret organization intended to protect members from employer retaliation, after the railway strike in 1877, it abandoned its secrecy in 1879. The organization grew in membership, hitting its peak in 1886 with 700,000 members. However, attendance began to decline sharply as a result of some 1,600 strikes, including several violent strikes and the Haymarket Riot in Chicago. This led to dissatisfaction in its organization, as well as a rise in anti-unionism, ultimately leading to its eventual demise.
On the evening of April 3, 1888, Valentine Hilsendegen died in his home after several months of illness. He was 62 years old.
In 1892, the City began to make owners install fire escapes on their buildings. One of the buildings singled out was the Hilsendegen Building, which was used for stores, offices, shops, assembly halls and sleeping rooms. The Trade Council moved into Room 7 in the building on April 6, 1893. Room 9 was leased by the independent labor party.
Shortly before 10 p.m. on July 3, 1898, a fire was discovered in the east wing of the building. The blaze was extinguished in about an hour, but not before causing between $15,000 and $30,000 in damage (about $590,000 to $1.2 million in 2025). Damage included losses to the Trade Council and the tailors who worked on the top floor. Luckily, the fire happened on a Sunday because no one was in the building at the time of the fire according to the fire and police departments. No other buildings were damaged by fire. The fire was believed to have been the result of a stray firework. By the next week, architect Joseph E. Mills was preparing plans to rebuild the damaged sections of the building, included with this were extra improvements, though what they were weren’t stated in newspaper reports.
There was a printing shop on the third floor of the building as of 1904 owned by Louis P. Ganger.
Uncertain times
On April 1, 1911, Elizabeth Hilsendegen, widow and controller of her husband’s estate, entered into an agreement with Samuel Mintz for him to purchase the building. She had since moved to New York and not particularly interested in holdings in Detroit. After a year of negotiations and a second potential buyer claiming rights to buy the building that were ultimately unauthorized, Mintz bought the building on April 11, 1912. The Detroit Free Press reported that the sale was about $400,000 (about $13.5 million in 2025). With this came talk of the possibility that the building may be demolished for either a hotel and theater or a department store. Rumors like this had been floated a decade prior, however, both did not come to pass.
John C. Hartz’s store, which had operated there since the 1880s, closed in 1914 and was replaced by the Waldorf Shoe Co. On Jan. 14 of that year, an article in the Detroit Free Press stated that the building was called a public nuisance and in poor sanitary condition, according to the board of health inspectors. At this point, the building housed several stores, as well as more than 20 Greek immigrants living in the upper floors, most of whom worked for the Ford Motor Co.
A month later, more complaints had been made and the owner was told by the health authorities that he may have to discontinue the use of the upper floors of the building as living quarters. Repairs were apparently made, as the building would survive several more decades.
The year 1914 is also when the Monroe Theatre opened in the building. This small theater was one of the last to open in Detroit’s first theater district on Monroe Avenue and had somewhere around 250 to 313 seats. The architect and opening day are both unknown, but it was owned by Samuel Mintz. In late 1942, Edward Jacobson became the manager of the theatre and helped to turn it from a 10-cent grindhouse theater (charging about $2 in 2026 valuation) to a higher-class theater that charged 25 to 30 cents a ticket ($5 to $6 and change in 2026), slightly higher than the nearby Columbia or New-Bijou theaters, both charging a quarter. Exactly when this theater closed is not known, though it was still open as of Feb. 13, 1951.
Parking problems
In 1948, the Municipal Parking Authority stated that there was a shortage of more than 6,000 parking spaces in downtown Detroit. Its suggestions included tearing down buildings on the site of the future City-County Building, including the Avenue Theater, for temporary parking, as well as proposing a permanent parking structure, a three-story, $3.2 million structure (about $45 million in 2026) spanning two entire blocks on Monroe Avenue from Randolph Street to Farmer Street. That shortage would later be revised to 7,000 parking spots in the city and then again to 9,000.
In 1950, these plans were shelved after then-Mayor Albert Cobo asked for a delay as he opposed putting retail stores into the parking structure. On top of that, the Michigan Supreme Court held that the City could not condemn property for private use, leading to the project being canned.
On Aug. 18, 1952, a new plan was set forth by the Municipal Parking Authority to build a new parking garage over the site of the Hilsendegen. Instead of tearing down every building on Monroe Avenue from Randolph Street to Farmer Street (about 11 buildings), this new plan would tear down only five buildings, from the Hilsendegen Block to 126 Monroe, next door to the National Theatre. This plan would also widen Randolph Street by 26 feet.
Thiis plan sought to solve the Supreme Court’s objection by buying the property from the owners and then selling the land to private enterprises to build and operate the garage. If necessary, the City could build and operate the garage itself, but the director of the Municipal Parking Authority wrote in reports to Mayor Cobo that he would abandon the plan if private interests would build the structure instead.
That is exactly what happened. On July 10, 1953, a proposal for a $1.4 million ($17.6 million in 2026), five-story parking garage for up to 600 cars was proposed by a joint venture between the J.L. Hudson Co. and Crowley, Milner & Co. department stores on that spot. This plan would ultimately have retail spaces on the first floor of the structure. These plans were ultimately approved by Mayor Cobo.
By that point, the eviction of tenants was already in motion, with an advertisement from Philips Clothing appearing on July 5, 1953, in The Detroit Times stating that they had to be out of the building by July 13 in order for the building to be torn down. A Detroit News article from July 12 notes that fixtures from the Monroe Bar were being auctioned off.
Demolition of the Hilsendegen began July 27, 1953.
During demolition on September 17, 1953 the east wall of the building collapsed onto Harry Wanshon, killing him. Workers and firefighters tried to free him from the rubble for two hours. The collapse happened as a result of several tons of rubble from the upper floors piling up in between the barricade and the wall of the building, and when Wanshon removed a joist, the wall fell on him.
It would take just over a year for the garage to be finished, with it opening Nov. 24 1954. Known as the Bates Garage, it provided parking for downtown shoppers and office workers for years, but as businesses closed up shop, it fell into disrepair. It would be used as parking for the Greektown Casino-Hotel at one point, as a stop-gap, but be acquired by the Downtown Development Authority (DDA) in 2010. In more recent times, it was home to City Slicker men’s apparel store and some restaurants. The garage was sold by the DDA to Bedrock Detroit and demolished in 2013 to make way for the long-delayed redevelopment of the Monroe Block.
In Febraury 2023, Bedrock’s project was rebranded as The Development at Cadillac Square. It included demolition of the Pochelon Building and National Theatre, the latter of which had its Albert Kahn-designed facade disassembled for reinstallation on a new building in the development.