Terrance Williams and Felipe Santos went missing in 2004 and 2003, respectively, under similar circumstances in Naples, Florida. Both men were last seen being arrested by Steve Calkins, then a deputy in the Collier County Sheriff's Department, for driving without a license. Calkins claims he changed his mind about both arrests and last saw the men after he dropped them at Circle K convenience stores.
On September 4, 2018, actor Tyler Perry offered a $200,000 reward for any information leading to the location of the men or an arrest in the case. Al Sharpton of the National Action Network and Ben Jealous of the NAACP also joined Perry in raising awareness of the case.  The disappearances were covered by multiple television shows, such as the ID series Disappeared. 
|Born||January 17, 1976|
|Disappeared||January 12, 2004 (aged 27)|
Naples, Florida, U.S.
|Known for||Missing person|
|Home town||Chattanooga, Tennessee|
|Height||5 ft 8 in (173 cm)|
|Weight||160 lb (73 kg)|
On January 12, 2004, 27-year-old Terrance Williams went missing in Naples, Florida. Williams, a native of Chattanooga, Tennessee and father of four children, had recently moved to Florida to be near his mother, Marcia.  Williams' roommate, Jason Gonzalez, says he spoke to Terrance on the phone on the evening of Sunday, January 11, before heading to bed. Williams, who had attended a party that evening at a co-worker's house, did not then have a valid driver's license after being cited for driving under the influence, and the registration on his car was expired. He decided to drive to the party illegally after being unable to find another ride. Gonzalez became concerned when Williams did not return home and emailed Marcia on January 13 about his concerns. 
The Williams family called police and filed a missing persons report. Shortly afterward, Williams' aunt was able to track down his Cadillac, which had been towed from Naples Memorial Cemetery after obstructing traffic. The tow report was signed by Deputy Steve Calkins of the Collier County Sheriff's Department. The family contacted the sheriff's department and discovered that Calkins had filed neither an incident report nor an arrest. 
Marcia contacted workers at the cemetery, who told her that they witnessed Calkins pull Williams over and ask him for identification, which he did not have. Employees stated that Calkins patted Williams down and put him in the back of his patrol car. Before driving off with Williams, Calkins then asked the cemetery employees if he could leave the Cadillac in the lot. Calkins was witnessed returning to the cemetery between fifteen minutes and an hour later and moving the Cadillac from a parking spot to the side of the road. The car keys were found on the ground beside the car.  Following this witness statement, the Williams family repeatedly called the sheriff's department asking to speak to Calkins. Upon being contacted by dispatch, Calkins claimed to have no memory of making any arrests or having any cars towed on the day of Williams' disappearance. He was contacted later and claimed to have a somewhat better recollection of his contact with Williams.  
A few days later, Calkins' supervisors asked him to submit an incident report. Calkins' report states that he first came in contact with Williams at 12:15pm after noticing that his car was driving was "in distress".  Calkins claimed he followed Williams to the cemetery parking lot and that he asked for a ride to a nearby Circle K convenience store because he was late for work. (Williams did not work at the Circle K.) According to Calkins, after dropping him off at the Circle K, Williams told him the paperwork for the car was in the vehicle's glove compartment. Calkins claimed that he returned to the Cadillac and discovered that the proper registration was not in the car and that he felt deceived, so he called Circle K from his work issued cell phone and asked to speak to Williams. The clerk allegedly told him over the phone that Williams did not work there. According to the report, Calkins then called in the license plate number and found that the plates were expired. However, further investigation revealed that phone and surveillance records did not back up Calkins' story: there was no sign of Williams or Calkins on surveillance footage from the Circle K, and the phone records from Calkins' cell phone showed no call to the Circle K.  Circle K employees were interviewed, and no witnesses could be found to place Calkins or Williams there. At this point, Marcia filed a complaint against Calkins. 
A new lead in the case surfaced when the Mexican Consulate in Miami contacted Marcia to tell her about another man who had vanished in a similar fashion. Mexican immigrant Felipe Santos had gone missing three months prior, after Calkins claimed he dropped him off at another Circle K, approximately four miles from the location where he claimed he dropped off Williams. 
|Disappeared||October 1, 2003 (aged 24)|
Naples, Florida, U.S.
|Known for||Missing person|
|Height||5 ft 7 in (170 cm)|
|Weight||150 lb (68 kg)|
Felipe Santos, 24, was a Mexican national living illegally in the US in nearby Immokalee, Florida. He had been living in the US for three years at the time of his disappearance, and sending money back to his family in Mexico. Santos was last seen October 1, 2003, at approximately 6:30am. He was driving to work with his two brothers when he was involved in a minor car accident in Naples. Calkins cited Santos for reckless driving and driving without a license or insurance, and placed him in his patrol car. Santos was last seen riding away with Calkins. 
Later that day, Santos' boss contacted the county jail to post bail, and it was discovered that Santos was never booked. Calkins claimed that he changed his mind about the arrest because Santos was "polite and cooperative", left him at a local Circle K, and drove off.  The other driver in the accident contradicted that report, stating that Calkins was agitated about Santos' lack of documentation. "He just stated that he was tired of pulling people over that didn't have licenses," she said. 
Two weeks later, after Calkins submitted his incident report, Santos' family filed a missing persons report as well as a complaint against Calkins. An investigation cleared Calkins of any wrongdoing. Santos has not been seen or heard from since.  His wife, Apolonia Cruz-Cortez, has questioned the quality of the investigation into the disappearance, citing the fact that she has not been interviewed by investigators. 
Further suspicion was cast on Calkins when a recording of his call to dispatch requesting the tow of Williams' car revealed further conflicting statements. In this recording, Calkins described the car as abandoned and blocking the road. This statement contradicted both his incident report and the witness statements, both of which reported that Calkins himself moved the vehicle to its location blocking the road. Calkins joked with the operator: "Maybe he's out there in the cemetery. He'll come back and his car will be gone." He was also heard using inappropriate language during the call, describing the car as a " homie Cadillac". Calkins defended his misstatements to the operator, telling investigators that he was just "joking around" with a friend. Calkins insisted he moved the car to assist the towing company, as opposed to attempting to make it look abandoned.  
Approximately twenty minutes later, at 1:12 pm, Calkins requested a background check on "Terrance Williams", giving an inaccurate birth date—a specific date that Williams had previously given the police when he was arrested. This contradicts Calkins' earlier statement that he never knew Williams' last name or any other personal details. 
Because the main person of interest in the case was a police officer, the Florida Department of Law Enforcement and the FBI were called in to work on the case.  Various investigative techniques were used, including the covert placement of a GPS device on Calkins' vehicle and a forensic investigation of the patrol car. Cadaver dogs were used to survey the areas identified by the GPS, but these turned up no further evidence.   Calkins was subsequently fired from the department for providing conflicting information about both missing person cases and for not cooperating with the investigation. 
The case went without any leads for a number of years until 2012, when a number of national programs began covering the case, including Disappeared, Anderson Cooper 360, and Dateline NBC. In 2017, the Investigation Discovery series Deadline: Crime with Tamron Hall investigated the disappearances of Williams and Santos.   Entertainment mogul Tyler Perry went on Al Sharpton's MSNBC talk show to discuss the disappearances, offering a $200,000 reward for information in connection with the cases. 
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- Associated Press (10 January 2013). "Tyler Perry offers $100,000 reward as he joins Al Sharpton in push to solve mystery of two men who disappeared a decade ago after encounter with SAME sheriff's deputy". Daily Mail UK.
- Cardona, Alexi C. (August 26, 2017). "Missing Collier men Terrance Williams, Felipe Santos remembered at ceremony". Naples Daily News. Retrieved August 6, 2018.
- "Deadline: Crime with Tamron Hall | Watch Full Episodes & More! - Investigation Discovery". www.investigationdiscovery.com. Discovery Communications, LLC. Retrieved 19 September 2017.
- Mangrum, Meghan (31 August 2017). "Investigation Discovery show to feature disappearances of two Collier men". Naples Daily News. Retrieved 19 September 2017.