Lost in Left Field

Lost in Left Field

First Gloves: Don Kessinger

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Paul White
Jun 22, 2026
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From all accounts I’ve found, it seems that Don Kessinger is a really nice man.

He’s still married to his wife for over 60 years, served his country in the Army, ran chapel services during his playing days, received both the Lou Gehrig Award and the Danny Thompson Award, both of which are given to players who demonstrate great character, now runs a real estate business with his son, and got to see one son and one grandson briefly play in the big leagues. They’ve named the Don Kessinger Society after him at his alma mater, Ole Miss, to “recognizing individuals who embody character, leadership, and athletic excellence.” So it’s probably safe to say he’s a good guy.

That fact likely has a lot to do with how he managed to stick around the big leagues for 16 years and play over 2,000 major league games. I say that because his actual play on the field really didn’t warrant that sort of longevity.

I know why Kessinger got to the big leagues in the first place. He was an athletic freak in high school back home in Arkansas, where his school didn’t field a baseball team but he helped them finish second in the state anyway before the team disbanded. He quarterbacked the football team and was also the punter, and was chosen as All-State. On the basketball court he set scoring records and was chosen All-State in that, too. He also lettered in track. One of his teammates said he was the greatest athlete he’d ever seen, and he had numerous offers to play in college.

Kessinger chose Ole Miss because the University of Arkansas didn’t have a baseball team at the time. He went there on a basketball scholarship and ended up leading the team in scoring and being chosen All-SEC all three years he played for them. The same applied to baseball, where he was not only All-SEC but All-American, too. He had opportunities to play both sports professionally, but Kessinger decided to accept the Cubs’ offer of a $25,000 signing bonus.

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