To an outsider, it certainly LOOKS suspicious (or, at the very least, mighty ODD) that Jack Ruby “just happened” to be in the Dallas police headquarters when Lee Harvey Oswald was. I remember that, years ago, Dennis Miller had a routine in which he pictured a Dallas cop yelling, “Hey chief, the owner of the local titty bar is here and he’s packing a gun- should we let him in?”
It SOUNDS preposterous that Ruby would be there! But in truth, Jack Ruby was a glad-hander and a police buff.He used to hang out with BOTH cops AND gangsters, and imagined he was a close pal of both groups. NOBODY was surpised to see Jack Ruby at police HQ because he used to hang out there a lot. The Dallas cops AND the Dallas Mob regarded him as a harmless pest. Both groups humored him, and occasionally dropped by his club for free drinks.
On the day Oswald was killed, nobody in the Dallas PD was surprised to see Jack Ruby around. Everyone just shrugged and thought, “It’s just that dork Jack again. Hope he doesn’t get in the way.”
The problem is, everybody sort of knew Jack Ruby, but NOBODY took him seriously! Even AFTER he killed Oswald, Dallas police never stopped thinking of Jack Ruby as a dim bulb, and never regarded him as a guy the Mob (or anyone else) would trust with an important mission like rubbing out a key witness! The Dallas police chief told the Warren Commission, “If Jack Ruby was in the Mafia, the Mafia needs a new personnel director.”