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We made an investment in a start-up company that has grown in value 5x. Because it's privately held, there is no way to value it and no way to sell our interest to get cash out.  So her attorney agreed that we would hold it in trust until a "liquidity event" at which time we would split the cash 50-50.

A few days ago I got a heads up from my friend who is one of the company's co-founders. He knows I need cash and he thinks he can finagle a way to sell our interest. It would a substantial amount of money.

They have to know by today.

Here's my dilemma. Normally I would assume I have a fiduciary duty to tell my wife. However, this cash out would be a "favor" from a personal friend that is out of the ordinary course of business. No other investors have or will be offered this.  I don't know how much relational capital my friend will expend to pull this off, because there's attorneys, institutional investors, the CEO etc, that need to be persuaded to get the buy in.

I would almost prefer to stay in the investment: here's the main reason why. I was working on a plan to offer my wife a settlement deal, which includes dropping the custody dispute and giving her a lump sum in lieu of future spousal support. How do you think getting an unexpected windfall would affect her willingness to settle? The custody issue is far more important to me than the money.

My wife is obsessively focused on money and security, to the point where she plays up the drama to the world.  For example, last week after a blowout on the freeway, she insinuated to everybody that we didn't have the money to replace her bald tires, when we actually have $100K in our savings. (She took her best hurt puppy face into the tire shop that supports her non-profit and like a beggar spilled her sob story to get a mercy deal of 10% over their cost). Some of this is for sympathy of course, but I believe much of it is irrational but real fear. She shoehorns the facts into place to align with her emotions and her alternate reality makes perfect sense to her.

Do I sound manipulative, thinking this way? Am I an unethical scumbag for even bringing this up?

You don't want to be caught hiding assets.That's for sure.Her atty already knowing about this fund insures he's going to bring it up in discovery.I'd leave everything "as is" during the divorce process.

I spoke with an attorney and she said I absolutely need to disclose it or be in deep doo doo.  (I was going to anyway).

Furthermore, I would be violating the automatic restraining order if I pulled the trigger myself and ok'ed the shares being sold. (That, I was about ready to do unilaterally... .   whew!).