Brother Knows Best
Author's Note: Just a random AU because I wanted to write one where Michael gets Dean and Cas together.
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Michael never liked Dean Winchester. In moments when he allowed himself introspective honesty, he admitted that it was because the two of them were too much alike. They were both completely over-protective of their younger siblings and would do anything for their families. Which was why, Michael found himself plotting to get Castiel and Dean together. Because even God knew the two of them were far too dense to figure out that their affections were reciprocated on their own.
Dean was probably about eleven when Michael first noticed that he'd become fixated on Michael's youngest brother. While Dean had always been a fixture in their neighbourhood, that year he became a fixture in Michael's house, too. Michael spent a lot of time casually sitting between him and Castiel that year. Of course, it only seemed to make Dean more determined to get close to Castiel. Michael learned that the easiest way to get Dean to back away was to imply that there was something going on between him and Castiel. It worked right up until they were thirteen.
When Castiel turned thirteen, Michael noticed that Dean wasn't the only one leaning in when they had their in depth discussions about popular culture. Michael wasn't going to have any of that happening under his roof (never mind that it was really dad's; dad wasn't here) so he had Gabriel give Castiel the Talk and let him use as many props and other audio visual aids as he liked. Castiel must have shared some of that presentation with Dean because even he seemed to back off.
When Dean was fourteen, he found his first steady girlfriend. Michael found his hatred of Dean Winchester increased exponentially that year. No one was allowed to break Castiel's heart. But Cas was only fourteen, and he put all of that stress and aggravation into school work and the debate team and Dean didn't come around so often, so Michael thought that was the end of that. He patted himself on the back and devoted his time to encouraging Gabriel to find gainful employment.
But somewhere along the line Raphael mentioned that volunteering would look good on a college application, and seventeen-year-old Castiel ended up tutoring thirteen-year-old Samuel Winchester. Michael was reintroduced to Dean Winchester when he came storming into their house determined that Sammy was way too smart to need a tutor and that Castiel could take his all-knowing, holier-than-thou crap and shove it back up his ass.
Michael saw that it was the work of two sentences before Dean was calmly apologising for jumping to conclusions and saying of course he didn't want Sam growing bored with work he was too advanced for and of course Sam was ready for high school courses. At that point, Michael knew there was no way he'd be able to stop what was between his brother and the uncouth Winchester kid.
By the time Castiel turned eighteen, he and Dean were dating. Michael said nothing about it because he still didn't exactly like the idea, but Castiel was smiling more and Dean was making an effort to be polite in his presence. But when Castiel accepted his place at MIT and Michael heard that Dean was going to be working full time at the auto shop, he sucked up his own feelings in deference to his brother's and asked about it. That was when Michael found out that Dean and Castiel had never been dating.
Michael was perhaps a little over-eager when he heard this news. He bought Castiel a car and might have implied that the only way to get to MIT from Kansas was to go on a three month long road trip with his brothers, and certainly not with any Winchesters who, since they were now employed full time, couldn't possibly spare the time. Michael was pretty pleased that he managed to get Castiel out of the state before Dean showed up for his first full day of work. Even if he had had to let Gabriel and Lucifer go with him. He spent the period with only Raphael for company, working on his anger management.
After that, Michael made sure he and his brothers spent every holiday together. (And if he was depressed and missed them the rest of the time, he wasn't going to let them find out.) But they never spent the holidays, or even Castiel's summer breaks, at home. Michael took the first one to Castiel. After that it was every state along the coasts and when those ran out, Mexico and Canada. The one time they spent Christmas in Lawrence, Michael knew that all four of the Winchesters had headed out of town on a holiday trip of their own.
Castiel got a job in Silicon Valley, and though the California weather didn't seem to agree with him, he actually seemed kind of happy. Michael let him stay there. With Castiel safely settled away from home, he didn't need to worry about the menace that was Dean Winchester any longer. Until Castiel called to say that he'd run into Sam Winchester who was attending Stanford University. Michael wondered how he'd managed to miss that. The only reason he had his car serviced at Winchester Auto was for the occasional facts he'd glean while he waited for them to change his tyres or his oil. But though Castiel and Sam formed a stronger friendship than the one they'd had growing up, it didn't mean that Castiel ever came home, and Dean never went to Stanford to visit his brother. Michael chalked it up to a near miss and refocused his attention on dealing with Lucifer's impulse control issues.
When Castiel was twenty-nine, the company he was working at went into voluntary administration and he found himself suddenly jobless. Michael was certain that an aimless Castiel was not a good one, so told his brother to come home where he'd have a job waiting for him in the family business. If he had to shuffle around everyone in the IT department, well, they should have known that nepotism thrived in businesses named after the families that ran them.
It was a year later before Michael realised that although he saw Winchesters all the time, Castiel didn't. It was also painfully clear that Castiel didn't see anyone outside of the company (and the family but since they all worked there now, that was implied). And talk in the neighbourhood book club said that it had been years since anyone had seen Dean Winchester out on a date with anyone. Michael worried that perhaps his focus had been misdirected throughout Castiel's youth. Clearly Castiel deserved Dean if he was the only person he wanted. His brother shouldn't have to settle. And if Michael had to knock some heads together to get them to see that, well, he'd knocked them apart. How hard could the opposite be?
Michael started small. He claimed that he was too busy dealing with a multi-national corporation to take his car for its six monthly service. He handed Castiel the keys and ensured that Dean Winchester was the only one working that day. When Castiel did not change his routine at all for the next week, Michael knew he had to be a little more obvious about it. He started talking about the Winchesters. He'd kept a cordial relationship with John Winchester over the years mostly as a way of keeping tabs on his overly-interested son. He usually kept the information he learned to himself, but he started slipping it into conversation with Castiel over their shared dinners. Castiel gave no indication that he paid titbits about the Winchesters' lawn any more attention than similar information gleaned from the book club.
After about a month of that, Michael decided to throw the subtle approach to the wind in a manner Gabriel or Dean would probably approve. "Castiel," he said. "I want you to become romantically involved with Dean Winchester."
"I am already romantically involved with Dean," said Castiel.
Michael blinked. "I beg your pardon?"
"Our fifteen year anniversary is next month."
"Next month?" Michael did the calculations in his head. "You've been together since you were fifteen?"
Castiel nodded. "Dean and I were aware that you did not approve of our relationship so we kept it secret from you."
Fifteen years. Michael felt a yawning hole inside himself. The baby brother he'd tried to help and protect his entire life had been lying to him for fifteen years. "Why have you never told me? I thought you two were dating when you were seventeen."
"Dean was not ready to 'come out' to his family."
"But Sam knew," said Michael. He'd had to maintain a distance from Castiel because he'd been forced to raise him, but Sam and Dean were closer than any two brothers ought to be.
Castiel nodded. "He was instrumental in facilitating the early stages of our relationship. Without him, our relationship might not have survived the distance and the disapproval."
Suddenly, Michael realised his attentions had been focused on the wrong Winchester brother all these years. He disgusted himself. "Perhaps it no longer needs saying, but you do not have my disapproval."
"Thank you, brother," said Castiel.
That didn't mean that Michael wasn't still trying to get a handle on his relationship. "I expect to see a ring on your finger soon," he said. "Fifteen years is far too long to avoid making a lifelong commitment."
Castiel nodded. "I plan on asking Dean to marry me on our anniversary. I suspect Dean has similar plans."
Michael fought down the ball of nausea lodged in his throat. "Were you ever going to tell me?"
"I had planned on it once Dean had accepted my proposal. This outcome is far more agreeable to me."
Michael had no idea which situation he would have preferred. Fifteen years. His baby brother had obviously grown up. What was he going to do with himself now? With Castiel obviously well settled, there was only one thing Michael could think to do. Death was too good for Samuel Winchester.