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Moneyball Blog

Apple’s Tim Cook & Microsoft’s Satya Nadella Would Be Brilliant at Trading MLB Players

Gary A Williams
August 4, 2025
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Apple’s Tim Cook & Microsoft’s Satya Nadella Would Be Brilliant at Trading MLB Players

gary-a-williams
Gary A. Williams wRatings Founder & CEO

All trademarks are properties of their respective owners.

Former Atlanta Braves GM and President John Schuerholz (1990-2016) had his own version of the NDA: “No dicking around.”

Last week was the Major League Baseball trade deadline. Only 30 General Managers exist – quite the exclusive club. So, you better not dick around or no one will want to trade with you. Be ready, be transparent, and be decisive when the time comes to make a trade.

Apple CEO Tim Cook and Microsoft CEO Satya Nadella would make outstanding MLB GMs. Trading players is just like business strategy. You must have your own view of value and how to win in a high-stakes environment.

Leadership in baseball and business know that winning requires anticipation. You must position your organization for its next move even though you are surrounded by competition every day. You need to know your strengths, weaknesses, and how your differentiation allows you to win.

And the key starting point for anticipation? Knowing your value.

MLB General Managers: Value Analytics

Every MLB team has an analytics wing attached to its scouting department. And each one has built a value system to evaluate talent and build their rosters. Some teams incorporate their Moneyball approach better than others to grab those undervalued resources. Lots of tools exist today to help MLB GMs.

One in wide use is ZiPS (Zymborski Projection System), which is a player projection system developed by FanGraph’s Dan Szymborski, that tracks player performance, aging, injuries, and other data. Stuff+ is another tool for just pitchers. It tracks velocity, vertical/horizontal break, arm angle, and release extension. Combine these with the original Moneyball analytics like OPS, and teams today are building extensive models on how to “buy runs, not players” (the Moneyball mantra) and win baseball games.

Four of this year’s top teams all made strategic moves to improve their chances of winning. And all four moved in entirely different directions to achieve their goals – something so many business executives fail to do as they simply to try to “copy” their rivals.

Last year’s champion LA Dodgers used ZiPS to identify key needs on the defensive front, adding player speed as well. They also showed their Moneyball prowess to build up their farm system.

The Houston Astros are leaders in the AL West. Pioneers of the analytics approach since the 2010s, the Astros made the riskiest moves to reacquire players that the analytics show are rebounding in their performances.

The Seattle Mariners are also just behind the Astros and may be the largest trade winners this season. Value-hunting is a core strategy for GM Jerry Dipoto, and they didn’t give up any of their top prospects to acquire hitters with favorable batted-ball data.

The San Diego Padres are just a few games behind the LA Dodgers in the NL West. Both teams are strong users of Moneyball analytics. Despite the Padres payroll limits, they grabbed two elite pitchers according to Stuff+ to build a top bullpen and possibly propel them to the World Series.

With his level of anticipation and understanding of value, Padres GM Preller might be on the short list to run a lot of public companies. He says the key is having a feel for value, and especially how other teams are valuing their players. This allows him to fit all the pieces into a puzzle to make the best decisions.

Business CEOs: Value Analytics

Running a company or managing a baseball team have a lot in common, starting with being surrounded by competition every day of the year. The end goal in business isn’t to win in October, but rather to win more customers and grow sales every quarter.

And that means you need a strong understanding of customer value so you can build strengths, spot weaknesses, and capitalize on those differences. Just like Baseball GMs use analytics to evaluate players, plan games, and optimize rosters to meet salary caps, business CEOs use analytics to manage talent, create customer value, and invest wisely.

Three of the best at this are Apple CEO Tim Cook, Microsoft CEO Satya Nadella, and Google CEO Sundar Pichai. They don’t try to be “all things to all people” – nor do they simply copy their rivals. Instead, they selectively choose which areas of value to “own” in their customer’s mind.

In our 2025-Q2 panel data, customers see Apple owning Innovation, Microsoft owning Availability/Choices, and Google owning Simple to Use. Clear differentiators amongst their peers. Digging into their financial results clearly shows their focus wins customers.

Recent Microsoft results confirm how customers value their Availability & Choices. According to the WSJ, the company is “minting money from corporate customers spending on regular technology.” Rather than buying their own IT equipment, customers are renting it from Microsoft’s cloud-computing service. Availability is “minting money” for Microsoft.

Google isn’t winning at that game, but it’s still winning because customers love how “Simple” Google search is. Critics said the company would lose market share in search due to AI replacing it. Just the opposite is happening. Google’s AI Overview tool has over 2 billion monthly users now, up from 1.5 billion last quarter.

Apple isn’t winning the AI war at all. Yet, customers still love its Innovation. They also believe in its Safety and Product Performance. Sales for iPhones grew an unexpected 13% last quarter, the highest increase in years.

Knowing where customers love you – versus your rivals – definitely pays off. Using analytics to build competitive advantages is no longer an option.

Just ask Meta CEO Mark Zuckerburg. While the company still prints money (by holding customers captive), Facebook is not a fan favorite with its customers, and he is being forced into huge pay packages to buy talent and stay up with his rivals.

Meta wants to unseat the smart phone as gatekeeper to the digital world, hoping to install a new vision for personal superintelligence. But Meta/Facebook lags far behind Apple, Google, and Microsoft in customer perception for Innovation. They failed with their VR goggles and are trying again with their “smartglasses.”

It is extremely rare for a company to overtake another that has such a firm grasp in a customer moat. The innovation moat, what we call Upstart Power, entails a whole new way to deliver value to a customer beyond just a single product. Customers need to see and trust the new ecosystem, something Meta has not been successful at doing beyond starting Facebook, and they buying Instagram and WhatsApp to fold it into his product portfolio.

In Moneyball terms for baseball, Zuckerburg is still trying to buy players when he needs to be buying runs.

Winning with Value Analytics

Get your customer’s view on value. Let our platform analyze your strengths, weaknesses, and how to be different in your customer’s mind.

You will be able to clearly see their expectations, your company performance versus key rivals, and how much more customers are willing to pay so you can grow revenues and margins today.

Don’t wait. Apply to become a wRatings Insider today.



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