$10 billion to buy Walgreens.
The man who did it almost never talks to the press.
In 2017, Bloomberg called his strategy the loneliest trade on Wall Street.
Stefan Kaluzny. Son of a pianist and a teacher, raised on Manhattan's Lower East Side.
Yale. Harvard MBA. Bain. The clean path.
In 1994 he left to cofound Delray Farms, a fresh grocery chain for low-income Hispanic neighborhoods in Chicago the big supermarkets had abandoned.
It didn't scale. By 1998 it was closing stores and shelving its national plans. The idea survived: find value where nobody else is looking.
He spent the 2000s buying retailers at Golden Gate Capital, then left in 2011 to start Sycamore Partners.
And bought what everyone else was running from.
Talbots, 2012: $193M, after every other bidder walked. Reportedly more than 6x back.
Hot Topic, 2013: $600M.
Belk, 2015: $3B.
Staples, 2017: $6.9B, in a year private equity had all but stopped buying retailers.
When Bloomberg profiled him in 2017, his 2014 fund was underwater. Forbes now puts Sycamore's assets above $13 billion and his net worth at $1.3 billion.
Walgreens shows how he thinks. Five things I'd want every founder to see in it:
1/ He bought the narrative discount. Walgreens was worth over $100 billion in 2015. He paid $11.45 a share, roughly a tenth of that. The "retail is dead" story set the price as much as the numbers did.
2/ He split it on day one. At close, Walgreens, Boots, Shields, CareCentrix and VillageMD became five separate companies. The market saw one struggling chain. He saw parts. If a buyer can carve your business into pieces, know what each piece is worth before they do.
3/ Part of the price is a promise. $11.45 in cash now. Up to $3 more only if VillageMD sells well. Contingent payouts shift the risk onto the seller. Count them as upside, never as price.
4/ He brought his own CEO. Mike Motz ran Staples US Retail for Sycamore. Now he runs Walgreens. A buyer with an operator waiting moves fast and knows your numbers better than you expect.
5/ He kept the biggest insider in. Stefano Pessina, who owned about 17%, rolled his entire stake. When a buyer asks you to roll equity, you are underwriting their plan. Sometimes worth it. Always price it.
Critics have a case too, on the same deals. Belk filed Chapter 11 in 2021 with Sycamore still in control. In 2019 Staples borrowed $5.4 billion and paid Sycamore a $1 billion dividend. Nine West went bankrupt and creditors came after the firm. Walgreens carries about $10 billion of equity under a total value near $24 billion with debt and payouts counted. The verdict comes in five years, not five months.
The dealmakers who move industries are rarely the ones you'd recognize at a conference. Kaluzny built grocery stores nobody wanted, then a firm around a sector everyone had written off, and never once chased the spotlight.