The most torturous career in MLB history

Jul 13, 2026 - 19:45
The most torturous career in MLB history

A few months ago I happened to be taking a close look at the 1987-88 Arizona Wildcats men’s hoops team and noticed that while they couldn’t punctuate an exceptional season with a championship, much of their team atoned for that at the next level, with flying colors. But while Steve Kerr, Sean Elliott, and Jud Buechler combined to win 13 NBA titles, the theme of coming up agonizingly short never ended for their teammate, Kenny Lofton.

A baseball convert who flourished throughout a 17-year big league career, I was aware Lofton had never won a World Series. But when I took a year-by-year magnifying glass to his career and the specific permutation of teams he played for and how their seasons unfolded, it was the type of one-in-a-gazillion story that seemed too bizarre to be true.

In a parallel universe, Lofton’s hands are littered with rings. Seemingly every year his team was the odds-on favorite to win it all entering October, and/or his team lost a playoff series in which his opponent was buried with all but the final nail in the coffin before coming back from the dead. Pitch a script of his career to Hollywood, and they’d laugh you out of the room. But that was the reality of the odyssey that was Kenny Lofton’s big league career.

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