Nathan Baker Lawsuit: Middle Finger Stop and $50K Settlement

The Nathan Baker lawsuit ended without a trial: the Saratoga Springs officer resigned in June 2015 after pepper-spraying a motorist who had raised his middle finger at him, and the city paid $50,000 in August 2015 to settle the driver’s threatened civil rights claim.¹

What Baker Did During the Stop

On May 16, 2015, Adam Rupeka, a 36-year-old Troy resident and contributor to the “Capital District Cop Block” Facebook page, drove through Saratoga Springs and extended his middle finger at Officer Nathan Baker, then 34. Rupeka later acknowledged he had gone to the city specifically to provoke an officer and record the encounter.²

Baker pulled him over and ordered him out of the car. When Rupeka refused and asked what crime he had committed, Baker shook a can of pepper spray, drew it from his belt, and sprayed Rupeka in the face while he was still in the driver’s seat.³ Rupeka was arrested and charged with resisting arrest, obstructed view, disorderly conduct, and obstruction of governmental administration.⁴

At the station, department video showed Baker grabbing the handcuffed Rupeka by the neck and shoulders to force him into a seat, moving his leg toward him, and brandishing a stun gun. Baker was recorded telling Rupeka, “You’re under arrest. All your freedoms are gone.”¹ Rupeka was eventually taken to Saratoga Hospital for high blood pressure and difficulty breathing. Video of the encounter, recorded by Rupeka on a Sony Handycam that police briefly confiscated, spread quickly online after he got the camera back on May 19.³

Charges Dropped and Baker Off the Force

Police Chief Gregory Veitch placed Baker on paid leave on May 18, 2015, and the department opened an excessive-force investigation.³ On June 4, 2015, Saratoga Springs City Judge Jeffrey Wait dismissed every charge against Rupeka at the request of District Attorney Karen Heggen’s office, which said the charges “could not be proved” and that dismissal served “the interest of justice.”⁴

The same day, Baker was moved to unpaid suspension, and Veitch announced he would seek termination.⁵⁶⁷

Veitch called Baker’s conduct “inappropriate” and “inconsistent with the department’s policies, training methods and values,” and said, “The job of a police officer is not to drive around delivering attitude adjustments to those citizens who show unmistakable signs of being in need of one.”¹

The $50,000 Settlement

Rupeka’s attorney, James Knox of the Hacker Murphy firm, filed a notice of claim against the city alleging his First Amendment rights had been violated when he was pepper-sprayed for raising his middle finger. A notice of claim is a required precursor to suing a municipality in New York.⁸

The matter never reached a full lawsuit. In mid-August 2015, the city, Rupeka, and Baker settled for $50,000, paid by the city.⁹ The agreement stated the payment was “not to be construed as an admission or indication of liability” by the city and required Rupeka and his attorney to keep the amount confidential. The figure became public only after the Times Union and other outlets obtained the agreement through Freedom of Information Law requests.¹

Why a Middle Finger Could Not Justify the Stop

The legal weakness in Baker’s arrest was already settled law in New York. In Swartz v. Insogna (2013), the Second Circuit, which covers New York, held that giving an officer the middle finger is “an ancient gesture of insult” that does not create reasonable suspicion of criminal activity and cannot justify a traffic stop or a disorderly conduct arrest.¹⁰ That precedent shaped both the dismissal of Rupeka’s charges and the city’s decision to pay rather than litigate.

What Happened to Rupeka After the Settlement

The civil resolution was not the end of Rupeka’s story. In September 2015 he flew a camera-equipped drone that crashed into a chimney at the New York State Capitol and was charged with reckless endangerment; a judge dismissed the charge on March 17, 2016.¹¹¹²¹³

Rather than appear in court, the pair fled to Mexico. On April 3, 2016, Mexican police found Rupeka dead in a Tijuana hotel room; Ogburn was unresponsive and died at a hospital later that night. Autopsies by the Attorney General’s Office for Baja California attributed both deaths to pulmonary thromboembolism, with clonazepam in their systems. Mexican authorities briefly opened a murder investigation and then closed it after the autopsy findings.¹⁴ With Rupeka’s death, the outstanding warrants were voided and the criminal case lost its active status.¹⁵

1
Times Union. Saratoga Springs Paid $50K to Settle Pepper Spray Case
2
Spectrum News. Saratoga Police Pepper Spray
3
Times Union. More Revealing Video of Saratoga Springs Police
4
Daily Freeman. Charges Dropped Against Man Who Flipped Off Upstate Cop
5
The Saratogian. Fundraising Effort Underway to Assist Suspended Police Officer
6
Troy Record. Saratoga Springs Police Officer Baker Resigns Following Pepper Spray Incident
7
Spectrum News. Saratoga Springs City Council to Discuss Fate of Officer
8
Daily Gazette. Saratoga Pepper Spray Victim to Get $50K
9
WAMC. Saratoga Springs Settles Pepper Spray Case
10
Justia. Swartz v. Insogna, No. 11-2846
11
Police1. Fugitive Cop Block Contributor Found Dead in Mexico
12
Times Union. Cop Block Regular Rupeka Arrested in Troy
13
Troy Record. Troy Man Who Flipped Off Saratoga Springs Cop Faces Sex Abuse Charges
14
Houston Chronicle. Adam Rupeka and Jennifer Ogburn Autopsies Finished
15
Spectrum News. Adam Rupeka and Jennifer Ogburn Death Investigation