Greystone’s Brain Drain

Prominent lender Greystone has seen a flood of departures in recent months - plus major investor Cushman is writing down its big bet

Greystone, one of the industry’s most prominent multifamily and healthcare lenders, is grappling w/ an exodus of top talent across multiple arms of the firm. Meanwhile, its major backer Cushman & Wakefield has taken a fat writedown on its investment, and is rethinking its approach to the JV.

The Steve Rosenberg-led shop has seen many big-ticket exits in recent months, across the production & executive ranks, with more in the works. A snapshot 👇

CRE Analyst: 2026 AI in Real Estate Survey

Everyone's talking about AI in CRE. Nobody's measured it. Until now.

The 2026 AI in Real Estate Survey is the industry's first rigorous benchmark of where adoption actually stands, what's getting automated, and where the biggest opportunities are emerging.

Early returns are already raising eyebrows: 100% of SVPs and MDs surveyed believe AI can displace at least 40% of entry-level work. A relatively small sample for now, but unanimous results are hard to dismiss. We need broader representation across the industry to make the data as useful as possible for everyone. The more complete the picture, the better we can all anticipate what’s next.

Greystone (Cont.)

  • Shaya Ackerman, who joined from Meridian to boost Greystone’s agency-lending biz, exited last May. Now flying his own flag.

  • “DUSty” Dan Sacks, the firm’s (and sometimes the country’s) top Fannie originator, was gone by last summer. Now running a new multi unit at CFG

  • Structured finance guy Eliav Dan was out around the same time. Now running his own firm, Cap Pointe.

  • Debby Jenkins: The Freddie leadership vet joined Greystone in a bespoke role in ‘23 to boost the AH business; was out by end of ‘25

  • Rich Martinez: The Freddie vet (once joint #1 on CO’s Power Finance list w/ Jenkins) was brought on in ‘22 to grow the multi platform and run point on the Cushman JV. He was later tapped to head agency lending production. Per company insiders, he’s expected to be out by end of Q1.

  • Rob Russell: The firm’s prez of special servicing has resigned, and is said to be going to Regions Bank

  • Thomas Wayda: The Philly-based dealmaker, who worked on non-agency business, jumped over to Morris Betesh’s debt brokerage Arrow in Jan.

  • Chip Hudson: Greystone’s co-COO informed staffers this week that he would be leaving, most likely by end of H1. "I'm excited for both my changing season [Biblical deep cut?] and for both you and the future of the firm," Hudson’s note, reviewed by The Promote, reads.

Now, it should be said that some of these exits were voluntary, others not. Still, they leave considerable production and management voids at a firm that will now be chaperoned more closely by its major backer: In late ‘21, Cushman invested $500M in Greystone, for a 40% stake in its agency, FHA and servicing businesses. In Cushman’s most recent earnings call on Feb. 19, the firm said it was writing down that investment by $177M (35%). “We made the Greystone acquisition in 2021 when market conditions and interest rates were much different,” said CFO Neil Johnston. “We continue to expect Greystone to be a solid contributor to earnings going forward, just at a slower pace than we originally forecasted.” Greystone has also had its hiccups w/ Fannie: the agency placed the lender on its pre-review list in early ‘25, but by Sept. it was removed.

When CEO Michelle MacKay was asked by a Raymond James analyst about the challenges w/ the JV and whether it would necessitate a change-up, she replied: “Let's just say we're being a little more hands-on in the JV with the operations and really helping to guide that management team to a more profitable business model.” If you’re familiar w/ the patois of public company CEOs, that is a big statement to make.

In a statement, Greystone said “we are grateful for the contributions of our departing team members and we wish each one of them well.” It noted $13B in total loan originations in ‘25, a $105B+ loan servicing portfolio, and its position as the “#1 overall lender for multifamily and healthcare HUD-insured loans.”

Guerrilla Marketing, Zeckendorf Style

Regular readers of The Promote will know how much we think about the perception-shaping games that developers play, and how the media is a key tool in that game (Wednesday’s Insider-only breakdown gets deeper into this). Advertising your project is one thing; making your project an event is another. And one way to do that is to not let anyone in until you’re ready*. After scoring $1B-plus of contracts (incl. a Downtown record-smashing $129M deal) at their 80 Clarkson St. (listen to our Zeckendorf Bros. Downtown Funk pod) sans a splashy sales launch or publicly listing the units, the Brothers Zeckendorf decided it was time for a NOS boost to get the remaining units over the line. They set up a sneak peek for WSJ Mansion reporter (and my fmr. colleague) Kathy Clarke, by a distance the go-to chronicler of the abodes of the superrich. The result is a splashy hype piece (Headline: I Got a Coveted Invitation to See New York’s Most Secretive Condo Project) that is worth 100 ad campaigns.

“It’s a little bit like producing a show on Broadway,” said William Zeckendorf. “You don’t know until the curtain goes up how it’s going to work out.” 🙇‍♂ Zeckendorfs’ partners on the condo are Atlas Capital and Seth Klarman’s Baupost, w/ Cale Street 🥬 & Farallon (made our inaugural Quiet Kings of Capital list) the lenders.

*We should note that this hush-hush strategy was pioneered by Steve Roth at Vornado’s 220 CPS (co-produced this doc w/ the B1M on that one). But that was on Billionaires’ Row – 80 Clarkson pulled it off at what New Yorkers have long considered a B+ location at best.

🎙 Larry's White Whale & Jamestown Puckers Up

“It’s the guy on Saturday morning being like ‘that guy at the bar last night was a jackass!’ That was you, man. Just 10 drinks deep.”
And all of a sudden you're sitting here having to redevelop the most scrutinized project in the entire world. And you're doing it when you don't have the money.”

In Ep. 50 (!), we trace Larry Silverstein's odyssey with the World Trade Center redevelopment, analyzing the new blockbuster Amex deal and the insurance, legal and financing battles that the developer has fought since 9/11. Next, we jump on our Zambonis and check out Jamestown’s push for a hockey team in Atlanta. And finally, Blackstone has a data center offering that it wants to share with the universe - of retail investors, that is.

💗 to our sponsors:
1) LoanBoss, the industry-leading debt management software: 1-click covenant testing, instant cash flow forecasting, and live forward curves!
2) Bravo Capital, a leading HUD and bridge lender. See how their precision underwriting means quicker approvals and higher proceeds for sponsors.

Listen on Spotify here, YouTube here or Apple Podcasts here. Brands: To get in front of our obsessed audience of CRE insiders, reach out here.

Quickies

Unquotable Quotes

The building holds value because of how special it is, so I wouldn’t say that RFR is just looking to get rid of it.
- Avison Young’s Alexandra Marolda, on marketing the architecturally stunning but financially vexsome Church Missions House

Puretz Deal Sets Off Wells-UBS Tiff (Insiders-Only) 🔒

Continue reading with The Promote Insider

Unlock this story and all premium content. Start your free trial.

BECOME AN INSIDER

What you get:

  • Exclusive content: Weekly deep dives, deal memos, insider breakdowns, and interviews
  • Expert columns: Analysis from the investment and capital markets trenches
  • Bonus podcast episodes: emergency pods, Q/As, deal walkthroughs

Keep Reading