The Promote Podcast: Windy City Tailwinds & Stadium Arcadium

Date: January 7, 2026
Hosts: Hiten Samtani and Will Krasne

Episode Overview

This episode kicks off 2026 with a comprehensive insider breakdown of three consequential stories shaping commercial real estate (CRE):

1. The unexpected inflow of major multifamily investment in Chicago
2. The boisterous business of stadium development and the profound role of real estate in sports
3. A landmark Freddie Mac refinance of Brooklyn walk-up portfolios, hinting at new liquidity options for previously overlooked assets

Along the way, hosts Hiten Samtani and Will Krasne deliver their signature sharp commentary, market war stories, and the industry wit that’s made the pod a must-listen for CRE insiders.

Quick Hits: Market Movers & Shakers

[01:49 – 05:45]

• Saks Bankruptcy Implications

  • Saks possibly filing for bankruptcy, highlighting distress in retail real estate.
  • Ben Ashkenazy, returning to offense after tough years, purchases the famed Neiman Marcus in Beverly Hills, reportedly for $50 million—a shockingly low price for such a prime location.
    • “He must have squeezed. I would have paid to be in that room with him.” — Hiten [02:47]

• SoftBank’s Move on DigitalBridge

  • SoftBank set to acquire DigitalBridge (formerly Colony Capital), reinvented by Mark Gansey as an AI infrastructure play.
  • Some investors feel the $4 billion valuation undervalues the company amid the AI data rush.
    • “He was completely right that that bet worked out perfectly. But for whatever reason, the market hasn’t really agreed with the stock.” — Will [04:48]
  • Brief history of attempted suitors and what the deal signals for digital infrastructure investing.

Main Story 1: Windy City Tailwinds – Chicago’s Multifamily Surge

[05:59 – 12:35]

• Chicago’s Perennial Underdog Status

  • The city has struggled with outflow, declining office markets, and public perception issues (“liberal, crime, corruption”).
    • “Chicago, which a lot of folks would say is uninvestable... Folks who are buying in this market right now are folks who then famously got their teeth kicked in, in the Sun Belt.” — Will [06:01–07:00]

• Why Investors are Returning

  • After getting burned in Sun Belt markets, institutional capital is hunting for overlooked, supply-constrained markets—enter Chicago.
    • “You don’t need a ton of population growth if you don’t have supply. You just need enough. And there is enough.” — Will [07:24]

• Recent Major Transactions

  • AIMCO Liquidates: Selling legacy assets as they liquidate—major Miami parcel (to Oak Row for $500M+), and a blockbuster Chicago portfolio to Latera for $455M (1,500 units, ~$300K/unit)
    • “This was honestly quite a shock to me. Latera is stepping in here...not a Blackstone, it’s not an FPA, it’s Litera and Latera’s equity on this rest. Is there equity?” — Hiten [08:11–09:01]
    • Latera/Respark as buyers signal new capital entering urban midwestern markets.
    • Discussion about the legacy of AIMCO and creation of AIR Communities (“defining apartment transaction of 2024 sold to Blackstone for $10B+”). [09:06–09:11]

• Supply & Demand Fundamentals

  • Chicago’s occupancy hit 95%+ in 2025, well above averages, with 4.5% YoY rent growth—outpacing other major US metros.
    • “The vibes are much better and it’s been backed up by the data.” — Will [09:34]
    • Contrast to Sun Belt/Austin: surplus supply = falling rents; Chicago’s steady growth is due to limited construction.

• Sun Belt Player S2 Enters Chicago

  • Scott Everett’s S2 Capital, known for Sun Belt rides, now leaps into Chicago, acquiring the famed Ovaltine Apartments (345 units, $100M+).
    • “All kudos to Scott because he had the same type of problems that other folks had and has worked through them and is now playing offense.” — Will [11:18]

• Market Cycles Wisdom

  • Takeaway: The surest bets become shaky, and ‘uninvestable’ cities turn to gold when the fundamentals align.

Main Story 2: Stadium Arcadium — Sports, Subsidies & Surrounding Goldmines

[13:35 – 21:53]

• Kansas City Chiefs’ $2B+ Public Funding Win

  • Chiefs secure jaw-dropping public subsidies for a new Kansas stadium; this is emblematic of a national trend.
    • “It’s unbelievable how big a gimme this is. It’s stupendous.” — Hiten [13:48]
    • The real estate and ancillary development (hotels, retail) is the windfall—teams profit from their venue’s surrounding action.

• Why Stadiums Matter in CRE

  • Increasingly, sports teams’ value is underpinned not by games or streaming, but by the real estate unlocked: year-round concerts, events, hotels, retail.
    • “What supports it is the other 150 nights a year when you can have Bad Bunny or whomever in concert...” — Will [14:55]
    • “Everything’s real estate. The Chiefs...all of this is real estate.” — Hiten [14:54]

• The ‘Anchor Asset’ Effect

  • Stadiums now regarded as ‘anchor assets’ that catalyze neighborhood transformation.
    • Examples: Chase Center (San Francisco), Battery (Atlanta), Nationals Park (DC), Barclays Center (Brooklyn).
    • “They can be really catalytic, but especially if you own all of it around.” — Will [16:15]

• ROI Skew: Owners vs. Public

  • Public subsidies disproportionately benefit team owners and developers—returns for taxpayers are dubious.
    • “The ROI seems to be quite handsome for everyone except the public.” — Hiten [16:22]

• Political & Financing Machinations

  • Stadiums’ success often hinges on political will and being seen as ‘builders’ by politicians—despite being money losers for cities.
    • Stories of stadium deals in Atlanta (Centennial Yards by the Ressler brothers, Tony and Richard; Tony also owns the Hawks and founded Apollo and Ares), Boston (Kraft family, new MLS stadium), Philadelphia (76ers’ bitter parking fight), DC (Commanders return with $1.1B public fund), NY (Dan Doctoroff’s West Side stadium vision catalyzed Hudson Yards via mega-development financing).
    • “Some of the most successful large scale developers...really understand the political machinations of financing things like this.” — Hiten [18:52]

• Future Model: Live, Play, Work Next-Gen Stadiums

  • Incorporation of immersive event spaces like COSM; stadium-anchored, mixed-use destinations are the model.
    • “You’ve got the real stadium for the live experience. You’ve got cosm...and then a whole smorgasbord of retail, F&B…” — Hiten [19:41]

Main Story 3: Brooklyn Walkups Go Institutional – Big Freddie Mac Refi

[22:02 – 26:39]

• Carlisle & Greenbrook’s $500M Freddie Mac Refi

  • Institutionalizes Brooklyn walk-up ownership, once considered unbankable by large lenders.
    • “Carlisle and Greenbrook have just got a close to $500 million refi on their walk up portfolio in Brooklyn...They’ve done it and they’ve done it via Freddie Mac. So pretty interesting deal.” — Hiten [22:02]
    • Portfolio: 260+ properties, ~1,000 units, all in choice neighborhoods.
    • Debt basis: ~$500k/unit, rents are market rate and properties held in the favorable 2A/2B tax class.

• What’s New and Why it Matters

  • Freddie Mac typically avoided small-unit assets; this opens liquidity for these portfolios.
    • “They did this refi...this means they’re staying in it for a while. Cash flow must be good. They think there’s further juice on the bone here.” — Will [22:32]
    • Freddy’s due diligence, liquidity, and back-office expertise allow this new wave of institutional capital; potential model for others with generational portfolios.

• Broader Debt Market Implications

  • Post-Signature Bank and NYCB retreat, agency finance fills the gap—could lead to more trades and upgrades in Brooklyn’s “yuppie” multifamily scene.

Notable Quotes & Memorable Moments

• “Would you rather have a couple thousand apartments in Chicago or one piece of dirt in Miami?” — Hiten [08:06]
• “You don’t need a ton of population growth if you don’t have supply. You just need enough. And there is enough.” — Will [07:24]
• “Everything’s real estate. The Chiefs, Bob Kraft supporting MLS...All of this is real estate.” — Hiten [14:54]
• “What gets financed gets built. And I think the most successful stadium developers understand that.” — Hiten [18:49]
• “The ROI seems to be quite handsome for everyone except the public.” — Hiten [16:22]
• “With Freddie playing this space, it sort of creates an opportunity to finance these things. Because as NYCB retreated, Signature bank went under. There were fewer and fewer options for landlords to finance portfolios like this. So if the agencies are coming in, that’s a pretty good sign.” — Hiten [25:26]

Timestamps for Key Segments

• 01:49: Quick hits: Saks bankruptcy, Ashkenazy’s Neiman Marcus deal, DigitalBridge-SoftBank saga
• 05:59: Chicago as a resurgent CRE target; Sun Belt pain, supply/demand thesis
• 08:11: AIMCO liquidates; Latera’s major Chicago buy
• 09:34: Chicago rent growth, supply/demand, resilience vs. Sun Belt
• 11:06: S2 Capital jumps into Chicago multifamily
• 13:35: Stadium development deep dive; KC Chiefs, public subsidies
• 14:55: Stadiums as real estate catalysts; year-round profit, not just game days
• 16:22: ROI for public vs. private; politics of stadium funding
• 17:27: Atlanta/NYC stadium development as economic anchors
• 19:41: The rise of immersive stadium-adjacent developments
• 22:02: Brooklyn walkup portfolio refi; Freddie Mac’s role and market impact
• 25:26: Agency finance: the new era for small-unit portfolios

Tone & Style

The conversation is fast-paced, irreverent, sometimes self-effacing, and always insider-savvy. Hiten and Will eschew buzzwords in favor of candor and dry humor, punctuating deep dives with playful quips and war stories. The emphasis is always on what moves markets and the unseen forces shaping CRE.

Final Takeaways

• Chicago is emerging as a surprise winner in 2026’s multifamily investment landscape—thanks to disciplined supply, stable demand, and capital fleeing boom-and-bust Sun Belt markets.
• In sports, it’s not just about the game; stadiums are now billion-dollar transaction drivers, serving as the nucleus for urban redevelopment, albeit often at public expense.
• Freddie Mac’s willingness to finance Brooklyn walk-up portfolios signals a tidal shift, promising new liquidity and institutional attention for an asset class once written off.
• Across all stories, the throughline is that what gets financed—by public, private, or agency money—gets built, and those who control the capital flows shape cities.

For more CRE deep dives, subscribe to The Promote Podcast or read the newsletter at thepromote.com