Cubs’ 2008 Trade: The One That Got Away

As the Chicago Cubs position themselves ahead of the 2024 trade deadline, it’s an opportune moment to revisit their eventful 2008 summer trade, which back then, viewed through the eager lens of a franchise hankering to quash a 100-year World Series famine, had finalized a deal they hoped would be transformational. Jim Hendry, the Cubs’ general manager at the time, sought to boost the team’s pitching roster by acquiring Rich Harden, a top-tier right-hander from the Oakland Athletics, along with pitcher Chad Gaudin.

The Cubs parted ways with a promising quartet—Matt Murton, Sean Gallagher, Eric Patterson, and notably, Josh Donaldson—to secure the Oakland pitchers. Donaldson, who was relatively under the radar at the time, would later unfold to become an MVP in the years to follow.

Back in 2008, the Cubs were performing admirably, boasting the National League’s best record at 54-36 and leading key rivals, with gains over both St. Louis and Milwaukee. Their successes had earned eight of their players spots in the Midsummer Classic, inflating hopes among fans that the long-awaited championship drought was finally nearing its end.

Harden’s stint with the Cubs initially seemed promising as he delivered an outstanding 1.77 ERA over 12 starts. Led by his arm and an enduring team effort, Chicago tallied an NL-leading 97 wins.

Nevertheless, their postseason dreams crumbled swiftly as they were swept by the Los Angeles Dodgers in the Division Series for the second consecutive year. Unfortunately for the Cubs and Harden, that peak performance in 2008 proved hard to reclaim; injuries plagued his career, leading him to retire by age 29.

The trade’s unforeseen consequence was the loss of Donaldson, who matured into a stellar Major League talent post-trade. Donaldson’s breakthrough came in the 2012 season with the A’s, after he transitioned to third base and nailed down a consistent starting role.

By 2013, he was a standout performer, finishing fourth in AL MVP voting and establishing himself as a prime player over the subsequent seasons. He clinched his first All-Star selection in 2014, his last season with Oakland.

Donaldson was traded to the Toronto Blue Jays before the 2015 season, where he experienced a career pinnacle winning the AL MVP and propelling the Jays to their first division title since 1993. He paced the league in runs, RBI, and total bases that year, securing another All-Star selection alongside a Silver Slugger award. His tenure at Toronto marked him as a dominant force offensively, a legacy that carried through subsequent stints with Cleveland, Atlanta, Minnesota, and a closing circle in Milwaukee.

Looking back at the 2008 trade, while the Cubs had landed a significant pitching asset in Harden, they hadn’t grasped the full potential of what they were giving up in Donaldson, who went on to accrue achievements including multiple All-Star appearances, Silver Sluggers, and an MVP title—a testament to the unpredictable nature of baseball trades.

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