How Red Sox Almost Missed Out On Dave Roberts Trade In 2004

The Boston Red Sox have some work to do with the trade deadline quickly approaching. While they did trade away Rafael Devers earlier this season, the Red Sox are firmly in the American League wild card race, meaning they will operate as buyers if they make trades at the deadline.

The trade deadline is a complicated time for teams across the majors, and if there’s one guy who knows that, it’s former Boston front office executive Zack Scott, who worked for the Sox from 2004 to 2020.

Sometimes, the obvious decision may not be what’s in the best interests of the franchise. Just look at the Devers trade; while the Red Sox were torched for trading their best hitter, they have powered their way into a playoff spot, while the San Francisco Giants are in a complete free fall, having lost 11 of their past 13 games.

If you don’t have any attention to detail, you could miss out on a potentially groundbreaking move. As Scott recently revealed, that very nearly happened when it came to Boston’s trade for Dave Roberts back in 2004.

“The Dave Roberts trade almost didn’t happen,” Scott wrote in a column for MLB Trade Rumors. “Theo Epstein asked an intern to research available outfielders. The initial list was terrible, but instead of dismissing it, he challenged the young staffer to think differently.”

“That’s when the intern heard the Dodgers were trying to acquire Steve Finley. Since they already had plenty of outfield talent, maybe they’d be willing to trade away Dave Roberts. The intern rushed to Theo’s office with the idea. Within hours, we’d made the trade.”

Trading for Roberts didn’t seem huge at the time, but he ended up playing a pivotal role in the Red Sox’s 2004 comeback in the ALCS against the New York Yankees. Roberts stole second base in the bottom of the ninth inning of Game 4, before eventually coming around to score the tying run. Boston would win in extra innings, and the rest is history.

Had Theo Epstein, who was the team’s general manager at the time, ignored this intern’s research, there’s a decent chance the greatest comeback in MLB history doesn’t happen. At the 2025 trade deadline, the Sox will work hard on making sure they don’t pass on any potential diamonds in the rough like they did with Roberts 20 years ago.