Officials said Gumersindo Reyes Jr., 51, was disguised as a woman Wednesday afternoon when he entered a Chase Bank on State Road 436.
Casselberry Police Chief Larry Krantz said Reyes passed a note to a teller demanding money and implying he had a weapon in his backpack. He left the bank after receiving a small amount of cash.
A deputy was driving by when Reyes ditched the disguise in the bushes outside a neighboring Pollo Tropical, officials said.
"(The deputy) noticed somebody coming out of the bushes. The deputy immediately confronted the individual, exited the car and saw bizarre behavior," Seminole County Sheriff Dennis Lemma said.
The deputy attempted to subdue Reyes by deploying his Taser, investigators said. A foot pursuit ensued between the deputy and Reyes across the highway and into an apartment complex, authorities said.
Investigators said as the deputy reached for his firearm to order the Reyes to the ground, Reyes reached for the gun. The deputy was able to regain control of the weapon, and as the altercation continued, the deputy deployed his Taser for a second time but was unable to subdue Reyes, authorities said.
Resident Corey Reid witnessed the altercation.
"At that point, I didn't know what could happen," said Reid. "They were tussling on the floor."
Deputies said Reyes then ran from the complex and got into the deputy's patrol vehicle. A chase then ensued between residential areas of Orange and Seminole counties, deputies said.
The pursuit ended in Maitland when Reyes crashed into a civilian's vehicle, investigators said.
Officials said Reyes has a criminal history in Puerto Rico on charges of attempted murder and robbery but has no criminal history in the United States.
There were no injuries reported.
The Sheriff's Office is expected to release body camera and dashboard camera video Thursday.