A/N & Standard Disclaimer: Thank you Mr. Sorkin for creating more great characters, hopefully you don't mind that I play with them from time to time.

This story started as a short character exploration and ended up as several chapters. They are all written and just need to be proofed and edited so I should be able to update fairly regularly. I hope you enjoy!

Charlie sighed and leaned back in his chair as he watched MacKenzie and Will verbally spar over which item deserved to lead the News Night program that evening. Deciding it didn't need to involve him he tuned them out, sitting forward in his chair to review the network ratings report for the 10 o'clock programming.

After a short while it became easier to concentrate which was distracting enough to force Charlie to look up from his work wondering why the shouting ceased. Will and MacKenzie were still in his office, no longer arguing but staring at each other intently.

Deciding the tension in the room needed to be dispersed Charlie interrupted their silent communication, "So it's settled then?"

It was clear from the matching startled jumps and awkward glances that they had both forgotten that Charlie was even in the room.

"Not really..." Protested MacKenzie.

"Don't worry, whatever you two decide is fine with me." Charlie explained with an addled tone and a smile while moving to open the door to usher them out.

"But…" MacKenzie began again until Will cut her off with a guiding hand on her lower back.

"Come on, Mac. Charlie's had his crazy lady quota for the day..."

"Crazy lady? If I'm crazy it's just because you make me so!" Charlie shook his head, hearing the former lovers continue to argue as they made their way down the hall.

He snorted under his breath as he thought the term "former" lovers. He really should find someone to place a bet with as to how long it takes forl the two of them to get back together. Though it was honestly taking them longer than he would have thought when he first pulled MacKenzie onto the News Night team just over a year ago.

If anyone asked he'd insist that he brought MacKenzie on board because she was the best in the business. He knew that both she and Will suspected his ulterior motivation of getting the two of them back together and even he would have a hard time denying it if either decided to press him on the subject. The old network executive simply cared too much for his star anchor to let him fall into the all too familiar trap of missed opportunities and staving off loneliness.

Charlie glanced at his wrist watch; 4:30pm, not quite 5 o'clock yet but close enough for him to pull a bottle of bourbon from the table behind his desk. As he sipped on the bitter liquid he thought about the young people who worked for him.

He had heard some nonsense about Jim and Don and some love triangle which MacKenzie was desperately inserting herself into, holding up herself and Will as a cautionary tale. He sighed and took a deep swig of the stiff drink.

MacKenzie had it wrong. An unfinished story couldn't be a cautionary tale. You can't find the morale to the story if you don't know how it ends yet. Just like he knew it was him and not Will or Mackenzie who was the true Don Quixote, Charlie knew that he was the true cautionary tale about of what happens at the end of the story if you don't fix what you've lost.