Orlando Approach Control has to handle some of the toughest airspace in the country. In addition to Orlando International (MCO), Orlando Sanford (SFB) also has air carrier arrivals. Orlando FSDO also awards 15% of all pilot certificates given by the FAA in any given year -- it is student-pilot central. Add to that the thousands of transients who buzz through the area on any given day. The airspace is chaotic, but somehow the Orlando controllers handle it all with aplomb.
Back in 2000, a buddy of mine and I instructed at Comair Academy (now Delta Connection Academy). The academy is based at Sanford, which sat under a 1,600' Class B shelf. Five miles north of us was a 3,000' Class B shelf. MCO arrivals from the north descended over our heads.
My buddy heard this on frequency (the tail number has been changed to protect the guilty)...
Aircraft: "Orlando Approach, Cessna 12345 over Sanford Airport at 4,500 feet. Request clearance into Class B."
Orlando Approach: (slight pause) "Uhh, aircraft calling, say again?"
Cessna 12345: "Cessna 12345 is 4,500 feet over Sanford Airport. We request clearance into Class B Airspace."
Orlando Approach: "Cessna 12345, we can't clear you into Class B airspace...you are already inside Class B."
Cessna 12345: (coming back quickly) "Cessna 345 is five miles NORTH of Sanford at 4,500 feet, request clearance into Class B."
(This would place him inside the 3,000' shelf instead of the 1,600' shelf, so his problem has not been solved.)
Orlando Approach: "Cessna 12345, are you over Sanford at 4,500 feet, or are you five miles north of Sanford at 4,500 feet?"
Cessna 12345: "How far north do we have to be?"
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When everything was sorted out, it turned out that the wayward Cessna was nowhere near Sanford or the Class B airspace. But until then, I can only imagine the excitement in the radar room as the controllers scrambled, looking for the blundering Cessna among the landing MD-80s and 757s.