The Pinkerton National Detective Agency’s work with hotels goes back almost to the founding of the Agency, starting with their standard detective work investigating thefts and liability claims as well as supplying in-house detectives and watchmen, both uniformed and plain-clothes. The Agency quickly expanded its work to include due diligence or background and character checks for employees and applicants to see if their experience, reputation, and personalities were a good fit. 

And, as the hotel industry grew, so did the industry’s unique threats and vulnerabilities. 

Because hotels cater to a floating population, or temporary residents, this can attract criminal activity. In their effort to eradicate crime and protect guests, employees, operations, and facilities, Agency leaders introduced their Hotel Testing Services. While this early form of risk assessment looked very different from a modern Pinkerton risk assessment, the Agency’s hotel tests were designed to disclose to hotel owners, lien holders, and mortgage companies site vulnerabilities and how these properties were being operated regarding service, thievery, and loss. In addition, the test would precisely detail the average guest’s experience from the moment of his arrival at the front door to the time of his departure, with special attention to the activities of taxi drivers, doormen, bellboys, porters, and other employees. During the 1920s and 1930s, hotel service tests also included the detection of bootlegging, illicit conduct, and other irregularities. 

The Agency sent in operatives who were both accustomed to first-class hotel services and familiar with pickpockets, confidence men, swindlers, and others who plied their activities on hotels and their guests. These specially trained operatives blended seamlessly into their surroundings.

Vintage black and white photo of a hotel lobby. A man on the left side of the photo is talking to a male hotel clerk, as they stand in front of a wall of mail slots. On the right hand side, another male hotel patron speaks with a man behind the bars of the cashier's desk.

Liquor, cigarettes, and companionship

While investigating one hotel’s service in 1923 — just three years into the Prohibition Era in the United States, when the production, importation, transportation, and sale of alcoholic beverages was prohibited — an undisclosed Pinkerton operative asked for a bellman to be sent to his room at 8:30 am at which time he requested a package of cigarettes and a morning paper. In a somewhat riveting report, the operative also said told the bellman that he felt “pretty tough and requested that he get me some liquor.” Bellman #3 — as he was henceforth named — replied that he did not ever sell any liquor and he did not know where he could secure any for the “guest.”

Then the operative asked if he knew of a female who could be sent up. The bellman replied that he did not and left the room, returning a few minutes later with cigarettes and a newspaper for which he was tendered a 10-cent tip. The operative reported that Bellman #3 was “very courteous, polite, and neatly uniformed. I then told him to have a waiter bring me a menu card.”

The next day, the operative told the hotel management that he decided to stay another night. They checked him into a different room, assisted by Bellman #12. 

“Before going up I asked him to bring a pitcher of ice water with him. It appeared to take him considerably longer than necessary to get this ice water, causing a wait of several minutes at the elevator,” the operative wrote, and then he made the same request regarding liquor and companionship. 

The bellman said, “I do not handle liquor.” 

The report makes no mention of a female. (More about this test below.) 

The report does detail that the operative wished to have his suit cleaned and pressed overnight off-site where it would cost between 25 and 50 cents. (The Agency asked operatives pack a somewhat soiled and wrinkled suit to test valet services.) Bellman #12 replied that all valet service was done in-house at a cost of $1. 

“The bellman was nice about this. I tendered him a 10-cent tip,” the Pinkerton wrote.   

Rumors of illicit conduct

There had been a buzz that the hotel’s housekeeping service offered more than simple housekeeping services.

“I returned to my room and found that the same had been made up. Clean towels, soap, and other conveniences were placed in the room and the same was neat and clean. I endeavored to get in conversation with the maids on the floor, but they appeared to have no time for other than their work, giving me no encouragement whatever,” the operative wrote. 

On another occasion during his stay, he wrote, “Leaving my door open I waited until the maid came around to this wing of the building. I then made an inquiry about where the other maid who used to be on this floor, explaining that the other girl was a ‘good sport.’ This maid appeared to be very familiar with the guests. Although I made several suggestions, she absolutely refused to enter my room.” 

Special tests for security and cigars

As detailed in the 13-page evaluation handbook, the Agency required operatives to leave their rooms unlocked at night and pretend to be asleep if someone entered — a secret test for watchmen and hotel security. The operative reported no irregularities or persons entering his room. 

The operative felt the after-dinner cigar service was exceptional, for which he tendered the waiter a 20-cent tip. “He was very attentive, businesslike, and courteous all through the meal,” the operative wrote. It should be noted here that the Agency recommended operatives limit their tips for any service to 10 or 15 cents to test the response “from the employees so tipped.” The Agency also requested that operatives spend no more than 15 cents on a cigar. The operative’s dinner bill, including a 15-cent cigar, totaled $2.30. 

The not-so-exceptional

Not all the employees and departments scored so well. While everything in the dining room was spotless, the kitchen staff were not thorough in their cleaning and sanitizing efforts or in their egg-cooking skills. 

One morning the operative ate in the dining room, and his hard-boiled egg was, “unfit to eat.” In addition, the inside of the egg cup was coated from a previous order of eggs. The saucer was also unclean and appeared not to have been washed. The waiter was apologetic and offered to replace the egg. The operative declined the request, “having lost his appetite for eggs.” 

When the operative had breakfast delivered to his room on another day, he ordered another hard-boiled egg. The waiter who brought the operative’s breakfast was reportedly rather sarcastic and not helpful. He returned the operative’s money for yet another inedible hard-boiled egg served in another dirty egg cup. He did, however, keep the 15-cent tip. 

Published November 29, 2022