A shocking early morning act of violence, a frantic New York Police Department search for a suspect and a gunman seemingly in the wind: The year was 2022, and the man the police had fanned out to find was Frank R. James, who had set off smoke grenades inside a crowded subway car in Brooklyn and opened fire.
Now, more than two years later, another manhunt has gripped the city. But unlike Mr. James, who was apprehended the day after his rampage, the man who assassinated the chief executive of a health insurance company just before dawn on Wednesday in Midtown Manhattan has not been caught or even identified after more than four days.
The two most recent fugitive searches in New York City have involved gunmen who made seemingly improbable escapes in a city teeming with surveillance cameras and people. But despite some similarities between the cases and the investigative tactics being used to try to solve them, the search for the man who killed Brian Thompson, the chief executive of UnitedHealthcare, has proved far more challenging.
The suspect’s ability to evade capture appears to be tied to his methodical planning, including wearing a mask and a hood during nearly all of his time in New York City and paying with cash everywhere, along with using a fake driver’s license.
And unlike Mr. James, who did essentially nothing to conceal himself after slipping away amid the chaotic aftermath of the shooting that wounded 10 people, the suspect in Mr. Thompson’s killing fled quickly into Central Park, away from the surveillance cameras that blanket much of Manhattan. He also appears to have left the state long before the police could possibly have begun to track his movements.
“I don’t think I’ve seen this level of operational preplanning in any crime, never mind in a murder,” said Kenneth E. Corey, a former chief of department in the New York Police Department.
Those evasive actions could blunt the effectiveness of the strategies the police used to capture Mr. James, including pleas to the public and photographs of a person the police are seeking plastered everywhere. Mr. James was captured after someone spotted him at a McDonald’s in Manhattan, mere miles from the crime scene.
Now, what had been a citywide manhunt has turned into a regional and nationwide search with help from the Federal Bureau of Investigation after the police said the suspect’s last known location was a bus terminal in Upper Manhattan.
Some manhunts end within minutes or hours, but others drag on for weeks or months. Experts say their resolution is usually the result of solid police work, the public’s assistance and a bit of luck.
“Manhunts are all very different, and they get more complicated when they go outside the area,” Mr. Corey said.
Mr. Corey, who worked in the Police Department when Mr. James fired 33 shots on the N train in 2022, said mistakes made by Mr. James led to his relatively quick capture. For instance, he left behind a credit card with his name on it and keys to a U-Haul van that had been rented under his name.
The police have had no such lucky breaks in their search for Mr. Thompson’s killer.
As the manhunt stretched into a fourth day on Saturday, the police continued to build a timeline of the gunman’s movements in the days before and the minutes after the shooting.
The man arrived in Midtown Manhattan on Nov. 24 on a Greyhound bus, the police said, and he was last seen on camera entering a different bus terminal near the George Washington Bridge about an hour after the shooting. There is no footage of him leaving that location, they said, leading investigators to conclude that he had left the city by bus.
On Friday afternoon, officers searching in Central Park for a second day found their latest clue in some brush: the gray backpack the gunman had worn during the shooting. It contained a jacket but not a gun, according to a person familiar with the case. The police have not found the man’s bicycle.
Brittney Blair, a former deputy in the Cook County Sheriff’s Office in Illinois, said detectives in New York City face distinctive challenges in tracking down the gunman. Some fugitives make it a game to taunt the police while on the lam, she said, such as the two snipers who terrorized Washington in 2002.
That does not appear to be the case here, she said.
“This subject had a mission, he plotted it out and his plans will be to try to evade capture,” said Ms. Blair, a senior director in the investigations and disputes practice at K2 Integrity, which advises companies on risk management and security.
And unlike Mr. James, who ambled around Lower Manhattan until someone recognized him, the suspect in Mr. Thompson’s killing left the city quickly and in a way that would be remarkably hard to trace.
The suspect’s last known location, the George Washington Bridge Bus Station, is a lesser-known terminal in New York City that largely serves commuters arriving from New Jersey. The terminal takes up a full block from Fort Washington Avenue to Broadway between 178th and 179th Streets. It also connects to a subway station for the A train.
The building is much smaller than the other Manhattan bus terminal managed by the Port Authority of New York and New Jersey, the busiest bus terminal in the United States.
In Upper Manhattan, the bus terminal’s ceilings of its lower-level lobby and its upper-level waiting room appear to be outfitted with dozens of cameras, and the Port Authority Police Department maintains a presence in the building.
When the man arrived there around 7:30 a.m. on Wednesday, the bus terminal in Upper Manhattan would normally have been “very busy,” said Miguel Rey, who manages the commercial space there. Buses and jitneys would have been disgorging workers from suburbs north and west of the city as the morning rush picked up.
The terminal’s 20 gates predominantly serve as a jumping-off point for commuters, mostly from bedroom communities across the George Washington Bridge in New Jersey, Mr. Rey said. About 20,000 passengers pass through that terminal on a typical weekday.
The first buses that are scheduled to depart the station after 7:30 a.m. are operated by New Jersey Transit and make stops in Fort Lee, N.J., and then other areas in northern New Jersey.
A schedule posted there for Greyhound shows that the earliest departure is later in the morning, after 10 a.m., for a bus bound for Boston, via Hartford, Conn. Other Greyhound buses depart the Upper Manhattan terminal for Philadelphia, via Newark. Another bus operator, OurBus, has a daily departure from this terminal to Buffalo at 8:20 a.m. on Wednesdays.
On Saturday, traffic at the terminal was subdued. Every few minutes, a bus or a jitney pulled in and unloaded or took on passengers. Several people sat on the steel chairs in the heated waiting room, where no music played and no TVs blared.
Anyone looking for signs that the terminal had played a role in the escape of a brazen killer would have found none.
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