Prompt: Nick Fury, five times he thought about employing the Winchesters and the one time he finally did
1.) Nick Fury could respect John Winchester's results. The former Marine had an impressive record before leaving the service and it only improved after his wife was killed. If there was a danger to civilians, Winchester made it disappear, no matter the personal risk. Then Winchester moved his damaged family again and Fury didn't care enough for the man's psych profile to track him down again.
2.) Sam Winchester caught Fury's eye while still in college. He had all of the Marine training without being a Marine. He was meticulous and as determined as a bulldog pursuing 'right.' He didn't mind paperwork; in fact, he attacked it with the same it with the same intensity as he did a supernatural danger. Then his girlfriend died and Fury had seen this story before.
3.) Fury used Dean Winchester as a training tool. New SHIELD recruits were supposed to find, approach and offer the lone older brother a job. Even with the superior qualifications of all SHIELD personnel, only twenty percent ever cornered him. Dean turned down every job offer, sometimes by flustering or scaring the recruit and sometimes by challenging them to a drinking contest that they inevitably lost.
4.) No matter how good Dean and Sam Winchester were separate, they exceeded all expectations together. They were a team better than anything training could create. Natasha would be able to beat one, but they would not separate and she would lose against both. Dean wouldn't let a SHIELD agent approach Sam. Fury would wait until their sibling relationship had recovered before sending Barton.
5.) Fury chatted with young Ben Braeden, ie Winchester in all but name. He told the teen in the presence of his mother that he respected Dean and that SHIELD could train him. It would give him a purpose and a team. Ben was tempted but he still had some growing to go. He had to mature first. Fury was looking forward to watching that future develop.
6.) (and the one he had employed) He browsed the coffee section, waiting to deliver the paycheck. He was mid-management now, but that would change. As expected, Winchester was on time, pushing a full grocery cart and with a toddler in tow. She was pregnant again. He wasn't surprised when she handed him her letter of resignation in exchange for the cash. No more dropping Dean off at a babysitter's for an afternoon mission to pay the bills. Pity. Mary Winchester was his most creative problem-solver.