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Off Duty · Sports · The Wrong Job

Everyone Told Him He Was an Executive. He Wanted the Uniform.

Will Venable had the Princeton degree, the Ivy League pedigree and a job working for Theo Epstein. He left the spreadsheets for the dugout, and his team — which lost 121 games the year before he arrived — is in first place.

By Sean Anees Saifi · Capital Wealth · Published Wednesday, September 16, 2026 · Source: The Wall Street Journal, September 16, 2026 edition, plus Tuesday’s market close as the paper printed it
Key Points
121
games the White Sox lost the year before he arrived
1st
where they sit in the AL Central now
0
Princeton graduates who had managed in MLB before
.385
his batting average as a Princeton senior
A worn olive canvas duffel bag spilling bats, batting helmets and a ball onto a wooden dugout bench at golden hour, chain-link fencing behind.
If the White Sox hold on, they would be the first team ever to reach October immediately after consecutive 100-loss seasons.
In one line: The obvious career was available, prestigious and wrong. The interesting detail is not that he chose differently — it is that the tryout that changed everything began with three swings and misses.

As his playing career wound down about a decade ago, Will Venable’s future looked settled to everyone but him.

“You can pick out the guys who should stay in the game,” said Bud Black, his longtime manager with the San Diego Padres. “With Will, my initial thought was: executive.”

It was a reasonable read. Before nine seasons as a major-league outfielder, Venable had majored in anthropology at Princeton, where he starred in both baseball and basketball. That made him an obvious candidate for the growing ranks of general managers with Ivy League degrees, and he landed the prestigious version of the job immediately: special assistant to Theo Epstein.

Then he left it. “I still felt drawn to the field,” he told Andrew Beaton. He was not satisfied spending the rest of his life poring over spreadsheets and analytical models. He missed the clubhouse, and the uniform.

The job he took instead

Venable, now 43, is in his second season managing the Chicago White Sox. When he took the job, the team had just set a modern record for futility by losing 121 games.

They are now the biggest surprise in the sport, in first place in the American League Central, playing a critical series against Cleveland this week. If they hold on, they would be the first team ever to reach October immediately after consecutive 100-loss campaigns.

Even without that, he was already somewhere new. In 280 years Princeton has produced two U.S. presidents, twelve Supreme Court justices, a couple of dozen Nobel laureates and three current major-league general managers. It had never produced a manager. Only four Ivy Leaguers have managed a full season in the past century, and none has won a playoff game since Yale’s Sam Mele with the Twins in 1965.

The tryout

Here is the part worth keeping.

Venable did not grow up planning on baseball, despite his father Max being a twelve-year major-league veteran. He dreamed of the NBA, and went to Princeton to play basketball for John Thompson III.

After his freshman year he took his mother’s advice and approached the baseball coach, Scott Bradley, about going back to the sport. Bradley took him to the batting cages for what amounted to an eye test.

He swung and missed a few times. Then he fouled off a couple of pitches. By the end of the session he was squaring up line drives. When he left, Bradley called his assistant coach: “The best player on our team just showed up.”

He became a two-sport athlete, averaging 10 points a game and taking the Tigers to the 2004 NCAA tournament — and hitting .344 as a junior and .385 as a senior.

Two things in this, both useful

The prestigious version of a decision is not the same as the right one. Venable had the credential, the pedigree and the mentor, and the industry had already decided what he was for. The job was available and it was wrong.

The first few swings are not the signal. He missed, then he fouled off, then he squared it up — and the coach’s judgment came at the end of the session, not the beginning. Almost every worthwhile process looks like failure in its first minutes, which is the reason so many get abandoned there.

He said something about Princeton that applies more widely. He was “in over my head” and often felt he did not belong, and he persisted anyway, eventually writing his thesis on baseball in the United States and Japan from an anthropological perspective. His adviser, Lawrence Rosen, said Venable “had a natural sense of how things were connected to other things that might not seem to be so connected.”

The White Sox already knew. Years before they hired him, they interviewed him for a managerial vacancy and gave him a written test. He did not get the job, but his answers stayed with the general manager, Chris Getz. “Man,” Getz thought. “There is something about this guy.”

What It Means For Your Portfolio

Hold — judge the session, not the first three swings

He swung and missed, fouled a couple off, then squared up line drives. The coach’s verdict came at the end of the session, not the beginning.

General planning principles, not advice for anyone in particular. Almost every durable financial habit looks like failure in its first weeks — the contribution that feels too small to matter, the reserve that earns nothing, the plan whose first year is unremarkable. The judgment that matters is made over the session, not the opening swings.

This is why the published rules carry review dates rather than reaction triggers, and why the model portfolios are not rearranged on a quarter of unflattering output. No change follows from a baseball story.

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