"He may have crawled into the Dumpster looking for his briefcase, or simply to get warm," said Fleisher, who runs a Center City investigations firm, Keystone Intelligence Network.
Fleisher also agreed with increasing speculation that Wheeler - who was filmed Dec. 29, two days before his body was found, in a downtown office with no overcoat and holding a shoe - was the victim of a traumatic event such as a mugging, or a stroke.
"He may have been mugged, as he himself suggested" in a conversation with a Wilmington parking-garage worker on Dec. 29, "and may have suffered a concussion," Fleisher speculated.
The crime-solving expert - who stressed that he hasn't seen Wheeler's confidential case records - said that if the body that turned up at the Cherry Island Landfill at 10 a.m. Dec. 31 had belonged to a homeless man, police likely would have explored an accidental death before launching a murder probe.
But Wheeler's prominence - he was a driving force behind the Vietnam Veterans Memorial in Washington and a former CEO of Mothers Against Drunk Driving, with degrees from West Point, Harvard and Yale - may have steered investigators to instead focus on homicide.
Fleisher's speculation came as police in Newark, Del., who are leading the investigation, conceded that they have no suspects. And another downtown Wilmington worker came forward with a disturbing account of Wheeler's wanderings before his death.
An unnamed Wilmington deli owner told Fox News that Wheeler entered the eatery at 8 a.m. Dec. 30 and had "super bloodshot eyes" as well as dirty cuffs and seemed homeless, but lucid.
And workers at two parking garages in Wilmington and a pharmacist in nearby New Castle, where Wheeler owned a home, have told police and reporters of encounters with a seemingly disoriented Wheeler. He told one of the parking workers that his briefcase had been stolen in a robbery.
However, none of these witnesses, whose accounts have been confirmed with two surveillance videos, initially reported Wheeler or his situation to the police.
Police continue to probe a bizarre loose thread in the case - whether Wheeler is linked to a Dec. 28 smoke-bomb incident in New Castle at the construction site of a home that he and his wife had tried to prevent with a lawsuit, claiming that the home blocked their view.
Not surprisingly, Wheeler's defense work - the Vietnam veteran was an assistant to the secretary of the Air Force in the late 2000s, specializing in cyber-warfare, and was a consultant for the Defense Department-advising Mitre Corp. - has already sparked Internet conspiracy theorizing, including a completely unsupported allegation that Wheeler had classified insight information about the mysterious death of birds in Arkansas.
But, Fleisher emphasized, the new evidence about Wheeler's disorientation suggests that he may not have been murdered at all. He noted that violent movement of the Dumpsters could have caused injuries to Wheeler or his corpse, which might appear consistent with murder.