A Villager’s search for a “sugar baby” on Tinder ended in a chaotic high-speed chase, a two-part crash at a local roundabout, and a gunpoint standoff.
David Allen O’Brien, 67, who lives in the La Crescenta Villas, was arrested late Tuesday night on four felony counts of aggravated battery and one felony count of aggravated assault with a deadly weapon.
According to an arrest report from the Sumter County Sheriff’s Office, the wild sequence of events began on the dating app Tinder, where O’Brien messaged a woman on July 12 announcing he was looking for a “sugar baby.” Over the next week, the two texted and struck an arrangement: O’Brien promised to give her “$1,000 each visit,” treat her to dinner, and take her shopping.
The pair agreed to meet on Tuesday evening. The woman had three friends drive her to the date, where she met up with O’Brien. The evening began as promised, with O’Brien handing the woman $200 and taking her to a lingerie store, where she purchased three items. They then went to dinner, where O’Brien handed her another $600, the report stated.
After dinner, the pair went back to O’Brien’s residence on San Bernardo Road. However, once inside the home, the woman told deputies she began to feel uncomfortable and texted her friends to come pick her up. When O’Brien realized she was leaving, he demanded his money back, stating “that was not the agreement.”
The woman refused, made her way outside, and jumped into her friends’ waiting car to flee the area.
Enraged, O’Brien hopped into his 2023 Ford F-150 pickup truck and chased the four victims through The Villages. When the victims’ car reached the roundabout at Buena Vista Boulevard and El Camino Real, O’Brien violently rammed the back of their vehicle, sending it crashing into a pole.
O’Brien then circled around the roundabout and rammed the car a second time, completely disabling the vehicle.
The four terrified occupants bailed out of the wrecked car. Three of them managed to run away, but O’Brien cornered one of the male friends. O’Brien drew a .22-caliber semi-automatic Ruger, pointed it directly at the man, and ordered him to get face-down on the ground or he would kill him.
The victim complied, believing he was about to be shot. However, as O’Brien became distracted while scanning the area for the three other victims, the man managed to scramble to his feet and run to safety. O’Brien prowled the area looking for the group until he heard approaching police sirens.
Deputies arrived on the scene and found O’Brien standing near his F-150 with the handgun still in his possession.
He was taken into custody and booked at the Sumter County Detention Center, where he was being held without bond.