This Has NEVER Been Explained! Please Read!

I think you are reading more into it. But you kinda answered your own question.

1. Cutter does airline security where he conducts classes with airline attendants for safety training should the flight they (the attendants are on) be hijacked.

2. Delvekio is the VP of a particular airline. Him and Cutter are close friends. Therefore in a sense, Delvekio can give business to Cutter, and Cutter can provide quality training to Delvekio's personnel.

3. During a particular class, Cutter and Marty did not get along. There was some animosity floating around after the training session.

4. Marty is an employee with Delvekios airline.

5. Delvekio was there when Marty and Cutter had their spat.

6. Delvekio wants Cutter to take a position in the company that would give Cutter more responsibility and a larger stake in the airline. To do this, Cutter needs to fly to "wherever" to close the deal.

7. Delvekio puts Cutter on a flight that Marty is working. Knowing that Marty and Cutter do not like each other, this is what the writers intended as the surprise.

8. Unbeknownst to Cutter and Delvekio, Charles Raine is placed on that very flight at the last minute with the "feds" not telling anyone anything.

9. Cutter see's Marty and though surprised doesnt seem to "understand" that this is the surprise that Delvekio intended for him. He doesnt understand because the flight doesnt land as planned w/o Cutter have to whoop ALOT of ass..

10. When the terrorists start acting up, Cutter assumes in my opinion 1 of 2 things. 1. That Delvekio created this mock scenario on an actual flight to see how Cutter would react or
2. That Delvekio had Charles Raine placed on the same flight as Cutter.
Either way, Cutter is under the assumption that the "surprise" is the terrorists on the plane and not Marty. Though one could logically conclude that Marty was the surprise even though it wasnt mentioned.

Some things to think about. Why would Delvekio knowingly place the worlds most wanted terrorist on his airline knowing that Charles Raine has a fetish with murder and destroying planes?

Delvekio is the VP of his airline. He can pretty much fly people for free whenever he wants as many times as he wants. Do you think its feasible that knowing that Marty is one of his employees, that he could place Cutter on a flight that he knew that Marty was working?

The feds DONT have to tell you who is in their custody or company. It helps with preventing escape attempts. It was just simply bad timing. Especially for the poor pilot and the innocent man with the daughter. Hope this helps!!!