Robert De Niro Prenup Breakdown Can Rock NYC Real Estate (And $500M Dynasty)

She claims the revised documents make her a 50% partner in all his post-marital success. Massive projects hang in the balance.

Taking on an empire is all about strategy and timing. You strike when the opponent is distracted and resources are already committed.

That’s the way Grace Hightower is evidently handling her second divorce from Robert De Niro, who hates publicity and has too much going on to suffer delays.

The stakes are high. He’s easily worth $300 million and with a $400 million Queens real estate development partnership with his broker son Raphael, there’s a lot more money coming in.

As patriarch, he’s also busy dealing with blowback from Raphael’s ex-wife dragging the family name into scandal headlines with racial and even predatory overtones.

So if Grace is tired of the marriage, it’s worth it for her and her lawyers to play hardball. Now is the moment to strike.

And the sad part is that a more relaxed and less flowery prenuptial contract could have avoided all this.

The agreement is clear

Grace has been with De Niro one way or another since 1987. They were married ten years later and almost split in 1999, only to reconcile five years after that.

Part of what dragged the divorce proceedings was apparently the lack of a firm prenuptial contract protecting his Hollywood money as well as his burgeoning New York real estate empire.

He’d already built Tribeca into one of the hottest ZIP codes on the planet, with restaurants and lofts galore. 

But those assets aren’t liquid. Splitting them up would get extremely ugly. 

When the couple got back together, the terms were laid out for the first time: $500,000 in cash along with what it would take to buy her out of the marital home. In addition, she’d get an apartment then valued at $6 million as well as $1 million a year in upkeep.

It sounded great when New York was still only a few years back from 911 and real estate prices weren’t quite so inflated as they are now. Unfortunately for De Niro, it also apparently confirmed in writing that everything he made beyond that point was a partnership, 50-50.

That may simply be flowery “sickness and in health” language, but it points to a vision of the couple’s relationship in which they worked together and would theoretically share the rewards if the bond dissolved.

New York is now an equitable property state so the court will take contributions into account when it comes to adjudicating the asset split. 

A “50% partner” sounds like she’s doing half the work to improve the assets De Niro brought to the table over the last 15 years if not the entirety of their relationship.

Unless De Niro meant it, there’s no reason to even go there in the contract. It can only hurt his case if the deal is tested.

His lawyers knew what they were doing. New York abandoned the common law marital property approach in 1980, so equity was already in the air years before the deal was signed.

But realistically, a $6 million apartment and what might be only a 0.2% annuity on the rest of his real estate holdings no longer looks like an equitable split at all.

Good prenuptial contracts get reviewed just like estate plans. If they’re out of date, it’s worthwhile to go back and revise the documents to something more current and defensible.

De Niro might’ve only been worth $100 million then. Here at easily triple that net worth, the numbers no longer add up the same way.

A few million-dollar gifts or projects in her name would have gone a long way over the years to keep her happy and put them on more equal footing when and if they eventually broke up. 

He didn’t do that and now he’s spent months in court.

No split possible right now

Meanwhile, he’s in deep trying to renovate an entire neighborhood of Astoria into a Hollywood-style film production hub.

Just buying the land is costing close to $75 million. It’s not all his money – son Raphael (from a previous marriage) is a high-powered real estate broker lining up venture investors – but a lot of the skin in this game is his.

After all, he was hoping to sink a whole lot more cash into the project and ultimately end up with a seriously valuable asset at the end of the process.

Doing all the work could ultimately cost $400 million. It could be worth billions.

But it will also take years to pay off. In the meantime the money is sunk. Backing out now could doom the entire proposition or at best lock De Niro out of the rewards.

He doesn’t want to do that. He needs his cash to stay right where it is, keeping the capital structure humming without spooking the outside investors.

If Grace wants $50 million or even $10 million now, he and Raphael could be looking at big headaches.

Raphael is distracted right now as well. His ex-wife Claudine is now with Cuba Gooding Jr. at the center of controversy over public sexual assault.

She’s borne her share of headlines in the past alleging racism and household staff abuse. Not Raphael’s problem any more but raising questions around the family is not what the De Niros need right now.

They need to focus. Maybe it means handing Grace participation in the new project instead of cash. After all, “50-50” partners don’t cash out early when big gains are on the horizon.

Maybe De Niro can’t do that or won’t abide it. We don’t know much about how his real estate empire is structured. Presumably there are partner shares he can transfer. 

If not, it means borrowing or liquidating properties to come up with cash. Neither is likely a pleasant scenario. He may already be profoundly leveraged as it is.

We’ll see how it goes, but again, it’s ironic that the prenup is the problem here.

And it’s about the empire he leaves behind. He’ll be 76 in August. He wants visitation rights with his youngest daughter and something monumental to leave all the kids.


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