In 2009, Lloyd Blankfein made Gerry Cardinale turn down what could have been the biggest win of his career. The Goldman Sachs dealmaker had the opportunity to buy a majority stake in the Liverpool soccer club. Cardinale knew little about the English team, but he could tell that Liverpool had great potential to exceed its £300 million (roughly $450 million at the time) price tag.
The investment committee rejected the deal at first, but Cardinale was able to sway them after bringing on the Yankees Organization and the Dallas Cowboys as coinvestors. But Blankfein, Goldman’s then-CEO, put the kibosh on the deal, fearing Goldman could get bad press from managing a sports team with such die-hard fans.
Cardinale took it in stride, but it made him think about leaving the bank to hang his own shingle.
“We were ahead of our time in taking a run at Liverpool, but in hindsight, I understand the decision,” Cardinale said in an interview. “I always joke to my friends at Goldman, ‘You guys cost us a lot of money.'”
He retired from Goldman Sachs in 2012 after 20 years and launched RedBird Capital in 2014. Today, RedBird is a go-to dealmaker in sports and entertainment with $7.5 billion in assets and 65 employees. Cardinale, now 55, finally got to invest in Liverpool last year by taking a stake in its owner, Fenway Sports Group, at a $7.35 billion valuation.
In the past year, Cardinale has attracted the kind of buzz usually reserved for his portfolio companies. He bought the soccer club AC Milan in August, earning the attention of the Italian press. He courted the ex-Disney CEO Bob Iger before Iger returned to his former employer, and partnered with Jeff Zucker, the ex-CEO of CNN, on a new $1 billion joint media venture