Target's underdog CEO is aiming for another bull's-eye as he writes his final chapter

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To unpack the 40-year-plus leadership journey of Target (TGT) chairman and CEO Brian Cornell, you have to head to the fenced-off basketball courts in the Whitestone neighborhood of Queens, N.Y.

The area wasn't always a magnet for upper-middle-income families, and Cornell wasn't always decked out in a fitted white button-down, dark slim-cut jeans, and black leather loafers.

"I grew up largely without a dad," Cornell, 65, told me in a new episode of Yahoo Finance's Lead This Way. "I had the support of my mom and tremendous support from my grandparents, who actually lived in this neighborhood. It certainly wasn't a classic lifestyle where we say, 'All right, here's a kid who's going to grow up to be successful.' Certainly not run a company like Target. But I learned early on in life the importance of school and performing well in the classroom."

Back then, he was just a sports-loving kid who shoveled snow, mowed lawns, and washed trucks to buy sporting equipment — a world away from high-profile jobs at PepsiCo (PEP), Walmart (WMT) owned Sam's Club, Michael's, and Safeway.

"I think if you grow up the way I did, you always feel like the underdog. You always worry about taking that step back," added Cornell. "So I think it has always given me a bit of a competitive edge, and you kind of lean in and make sure that nobody's going to ever outwork you and you're going to give it your all and try to perform every day."

Target chairman and CEO Brian Cornell (left) returns to his hometown basketball courts in Queens, NY for the first time in decades to share with Yahoo Finance executive editor Brian Sozzi (right) how he rose the leaderships ranks.
Target chairman and CEO Brian Cornell (left) returns to his hometown basketball courts in Queens, N.Y., for the first time in decades to share with Yahoo Finance executive editor Brian Sozzi (right) how he rose the leadership ranks. · Brian Sozzi

Cornell has taken that mentality and transformed Target into a modern-day big box chain, which features stationery and groceries alongside limited-edition Stanley tumblers and hand lotion from Dwayne "The Rock" Johnson.

It hasn't been an easy decade for Cornell, who likes to quote teachings by famed UCLA basketball coach John Wooden. But the chief executive is used to breaking through roadblocks, whether it be scrimping each week in Queens or leading an iconic retailer from a home base in Minneapolis.

Cornell's major CEO moments

A CEO's tenure is often defined by a few key moments. The right decisions tend to lead to impressive sales, profit gains, and, if the company is public, a higher stock price. The wrong moves will likely ensure a brief stay in the corner office.

Cornell has stood at many crossroads at Target — including on his first official day on Aug. 12, 2014.

As the first outsider to lead Target as CEO, Cornell came into a retailer often missing the mark. The company had been taking on heat from a data breach that impacted an estimated 40 million debit and credit cards. And prior management's dreadful foray into Canada was hemorrhaging money.