If you want to fly at Endeavor I would apply, the worst that will happen is they will say no. You will however have to change your "excuses" to reasons why you failed (take fault for the failure), and what you learned from each. Personally 5 failures is a lot and if you really want to do the airline route I would recommend one of the American wholly owned with that many failures.

I'm smelling troll here but just in case I'll add my $0.02...I got hired at 9E after 4 failures (3x initial CFI and 1x COM/ME)...HOWEVER, I had 21 squeaky clean years (aviation/job history/legal) after those failures and a fresh ATP certificate before applying. I also owned the hell out of my checkride failures in the interview. Go get some serious time and experience under your belt in the Part 135 or 91 world before applying to a 121 carrier. Based on what I've read so far however I'm questioning whether you have the right mindset for this job.

His post history looks legit.

This may be the case.

But it IS possible to slip through the cracks in GA and wind up getting taken advantage of with poor training. A young person not savvy in the ways of the world might not know to slam on the brakes soon enough, and wind up with a history like this.

I would be more than willing to assess someone's career potential based on attitude, work history, criminal history... but it's really hard to assess the OP's flying ability via the internet. As a CFI he should be in a position to contrast himself to other instructors and students.

It's going to be an uphill battle regardless, with that history. At this point there's probably no reason not to try a regional (obviously one with flow if he can get hired), he's already got the ratings .

Thanks for the advice. Will try first since what do I have to lose then look into part 135.

You may be the unluckiest person in aviation to get one bad examiner after another like that. It's quite a coincidence that each failure came down to a bad examiner, especially the ones that made you repeat maneuvers that you did correctly the first time. What were they thinking?

Apply to all 121 carriers. You will get picked up but please dont Blame anyone but yourself and have good examples to show how these failures made you a successful pilot. You may need about 10 years of clean 121 flying but it isn't the end of the road for you. If I made it to the legacy of my dreams so can you. Believe in yourself and know when to pump the brakes and speak up if you don't feel confident before a checkride.

Did you all your training at the same school? A pilot mill by any chance?
ATP maybe?
Your checkrides? Oh boy.....
It’s tough to learn but it’s decision making that seems to be lacking here.
Knowing when you’re ready for a checkride, changing instructors when you’re not happy. Knowing when weather is acceptable for a checkride.
And it’s perfectly acceptable for an examiner to retest all not just the ‘unsatisfactory’ items.
Especially if you’re showing weak skills.

* caveat
When YOU are under the hood the Examiner assumes all responsibility for see-and-avoid both traffic and weather.
However if you cannot recover from some ‘turbulence’ then it’s no bueno.

Story time:
I had a student fail one time because TWR told him to follow the Citation on final.
So my student turns base behind the first jet ( a Lear) and made the second jet ( a Citation) do a go-around.

Is it fair?
My student’s argument was that he can’t be expected to know all makes and models of corporate jets.
Well.....

If he didn’t know he should have asked the TWR.
My point being is that these things happen in aviation and they happen on checkrides. You’ll need to deal with it.

Teaching is kindling a flame and not filling a vessel.
If you’ve never wondered and asked about anything then specifically only what you’ve been taught.....you won’t do well in professional aviation.
Sorry.

Start learning.....

I dont think the checkrides will be the problem,some people just dont test well, the problem is going to be your complete lack of ownership. Any interviewer (121/135/91) is going to ask you about the failures. Giving the answers that you are giving here are not going to go down well. Taking checkrides for CFI and Comm but dont know how to do co-ordinated turns? Aircraft unusually heavy??

Sit down and think of the truthful answers to the questions. Be extremely prepared for the grilling they will probably give you if you apply. Endeavor may be out of your reach at this time, but hey, there is always Mesa!

Man, this sucks. You would think Twr would tell him he was #3 or something. I would imagine anybody could be suckered into this situation.