The Goldman Alum Who Reimagined the Yankees and AC Milan | The Deal

From George Steinbrenner to Jerry Jones, Gerry Cardinale has done deals with some of the biggest names in sports.
These days, the Goldman Sachs alum is making moves under the auspices of RedBird Capital, the firm he created in 2014. His purchase of the AC Milan soccer franchise and the resurrection of American football’s XFL stem from two decades spent at the intersection of sports, finance and media. Back when he was starting out on Wall Street, that nexus was a lot less obvious.
“I happened to hit an inflection point in sports that I couldn’t have possibly seen coming,” Cardinale said on the latest episode of The Deal with Alex Rodriguez and Jason Kelly. “We really hit an air pocket where you could really take off. Now the challenge is navigating that, because now everybody’s discovered sports.”
At Goldman, Cardinale got a chance to give advice to none other than Steinbrenner, aka “The Boss,” most notably about the 2002 launch of the YES Network. That debut brought its own made-for-TV drama, pitting Steinbrenner against New York Knicks and New York Rangers owner James Dolan (who also controls Madison Square Garden). Cardinale was in the middle of that fight as a key adviser to Steinbrenner-and his work took him deep into the Yankees front office.
“That really was sort of the career moment for me,” Cardinale said. “And I haven’t looked back. You really had that partnership with the Yankee organization, the Steinbrenner family-it’s been instrumental in everything I do.”
Cardinale and Rodriguez recall a Manhattan dinner they shared with Yankees President Randy Levine where they mapped out the roster that would ultimately deliver the 2009 World Series championship to the Bronx. Around the same time, Cardinale and Goldman teamed up with the Yankees and the Dallas Cowboys to create the hospitality company Legends, born in part out of Cardinale’s desire to link the ambition of Steinbrenner to the only other owner who could match him: Jerry Jones.
Leaving the lucrative confines of his Goldman partnership also opened up more opportunity for Cardinale to be an investor. He teamed with Dwayne “The Rock” Johnson and Dany Garcia to restart the XFL, and the trio subsequently engineered its merger with the USFL, the other big springtime pro -football league, to create the UFL. The new-look league played its first game earlier this week.
In 2021, Cardinale’s ambitions in team ownership led RedBird to buy a piece of Fenway Sports Group, the Boston-based company that owns the storied Red Sox baseball team, the Pittsburgh Penguins in hockey and Liverpool FC in English football. Cardinale then went a step further in soccer, buying AC Milan, one of the best-known clubs in the world.
Listen to The Deal on Apple Podcasts, Spotify, iHeart, Bloomberg Carplay, or wherever you get your podcasts. You can also watch The Deal on Bloomberg Originals and Bloomberg TV.
00:00 - 01:05 Introduction
01:05 - 05:21 The YES Network deal
05:21 - 07:36 Goldman Sachs in the nineties
07:36 - 12:01 Legends Hospitality & Jerry Jones
12:01 - 16:24 The uncertainty of the YES deal
16:24 - 21:31 Gerry & Alex on rebuilding the Yankees in 2008
21:31 - 23:28 Gerry’s relationship with George Steinbrenner
23:38 - 26:25 George Steinbrenner’s letter to Alex
26:25 - 36:49 Buying AC Milan
36:49 - 40:11 What Gerry learned about ownership from George Steinbrenner
40:11 - 42:01 Why invest in Italian football?
42:01 - 45:18 Inside the XFL
45:18 - Gerry’s advice for young people
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[@1H9A7M6]

Thank you for having GC on this amazing Podcast. It was a great insight to understand GC. He knows his stuff and he might be the greatest modern day visionary for our Milan and Serie A with his lofty ambitions. It’s an insightful look into the man. I noticed his clarity, patience, memory, approach and determination. Top notch. 👍🏽🔴⚫️ [The red and black colours are for Milan affectionately known as the Rossoneri in Italian.]

[@paulgilliland2992]

He’s getting a lesson in Italian bureaucracy as they slow walk approving anything related to a 70000 seat stadium.

[@SchnabeleBarr]

It’s just the mafia there. Corruption and corruption

[@Steph8010]

You can see how their Intelligence drops from when they talk about capital they've achieved in America when they speak about sports success in European football which they've never had and never will have, ESPECIALLY at AC Milan.

[@jorgipogi]

Great one! Very informative to learn the inner workings of sports and management. Arod should look into an advisory role with the Mets. The Mets really missed not being bought by Arod and his group. Arod really knows sports, both aspects-business and sport.

[@robertopusceddu4446]

❤️🇮🇹🏟️🇺🇲🖤 Cardinale Gerry: full speed ahead !! Building new STADIUM,in San Donato Milanese !!

[@SchnabeleBarr]

The stadium won’t be built 😂. Italian bureaucracy and their red tape are disgusting

[@jericho82]

He needs to sell asap no one like him in Italy

[@thomascamus3136]

As a Milan fan, I only wish the best for Gerry and his intentions for the club. Football is not just a sport but a business as well. I hope his intentions are pure for the club and for football and not only for the monetary or business side of it.

[@Steph8010]

If his intentions were true he would have certainly knew prior to the purchase of Milan it had 7 Champions leagues, When you don't factor that into the purchase of the club - it presents an immovable, inescapable truth to the fans that he isn't bright enough for the project he's marketing. AC Milan is a much bigger club than Italian people in Italy realise so listening to them purely and the American Milan fan does not relay the Scope that Milan has. It should be on 10 UEFA Champions league titles by now and this is the future.

[@4thelolzzlegit163]

Buy Zirkzee, extend Theo and Maignan's contracts and maybe I'll forgive you for not mentioning Paolo Maldini

[@Ksp0626]

Legendary intwrview god bless

[@Lorenzo-zl3oh]

Gerry build us an awesome stadium please!

[@robertopusceddu4446]

🇮🇹🇺🇲 thank you Cardinale Gerry !!👍 Great OWNER.

[@Steph8010]

*Venn Diagram Merchant.*

[@csabacrisan9412]

There's a gap between the English clubs and the rest due to tv rights. But if wealthy investors buy European clubs, combined with a change in the ffp rules, which i think is inevitable, will shift from financial to long term project. And here will lower that gap amongst the biggest clubs but unfortunately will increase with the others

[@HagaAdde]

Forza Gerry! ❤🖤

[@AbatchaAbubakar-sg4wh]

❤❤❤

[@franklinhopkinsjr1065]

I love this show…

[@AS-yc7lz]

Via dal Milan cardinale

[@SigmaBeta97]

Gasa Gerry.

[@Steph8010]

From now, Any time you speak publicly it will be studied, i need to understand everything about your past and future to work out how to expose this fraud. AC Milan is a powerful club Mr. St. Tropez. Shooting hoops 🏀 in st tropez and touchdowns in Sydney we will have a different approach next time cardinale, There is alot more attention on you now so we'll see you and your family in the public eye now mr st. Tropez 📿📿📿.

[@sandromalizia8928]

Caro Gerry devi ascoltare Ibraimovic l unico che capisca di calcio nel Milan, lascia perdere Furlani non è un dirigente di calcio L inter ha vinto il prossimo anno dobbiamo vincere noi, non prendere allenatori che non hanno mai vinto, prendili Italiani Sempre forza Milan

[@alessandroalberti4001]

sell AC Milan please

[@sireric41]

I get that you want a new stadium, but come on San Siro is arguably one of most iconic football stadiums in the world. Do whatever it takes to keep it

[@stefanotrevisan9376]

I’ve been there countless times. It’s imposing, majestic, iconic. It takes your breath away every time you walk inside. But it’s also cumbersome, decrepit and obsolete. The bathrooms are awful, the seats are too small. When you’re sit down, if you move your head you bump into the knees of the person behind you. There aren’t enough bars and services inside. It also shooks when fans jump too much - not in a good way, in a worrying way - and even some pieces of plaster fell down recently. As much as I love it, I’m totally up for a new, modern stadium, not to be shared with city rivals, more comfortable, that is owned by the club and not rented out by the city council.

[@csabacrisan9412]

Unfortunately, San Siro is not a 21st century stadium. From outside it was the most 'wow ' stadium I've ever seen, but inside needs so much renovation that it costs more than building a new one. Plus is owned by the city Council, therfore can't maximise on revenues. Also, due to bureaucracy they have to leave the city of Milano. It breaks my heart to say this because I love that stadium and I'm a Milan fan ❤🖤

[@dubfire77]

Imagine Milan winning Serie A and call themselves "world champions" :)

[@weronikarak3264]

Cardinale is a fool, ignorance level master, he is the worst owner of ACM history. He has no respect to ACM history and he is not a fan of football (for him soccer), he has no pasion and disare to winn trophies he only care about money