"I would say the one that didn't turn out well -- and the one I learned the most from -- was the Edmonds-for-Freese deal," Towers said recently.
Towers, currently a special assistant for player personnel for the Reds, spent the offseason of 2007 looking for some offensive punch and defensive impact in center field.
The Padres were coming off a season where they narrowly missed the playoffs, dropping the now-infamous Game 163 to the Rockies. Mike Cameron, who was the team's center fielder the two previous seasons, hit free agency that offseason.
Edmonds, an eight-time Glove Glover and four-time All-Star, was coming off the first down season of his career (.252/.325/.403), but Towers was hopeful for a bounce-back season with the Padres in his native Southern California.
"At the time, we were really looking for a center fielder, because we didn't have anyone in the system," Towers said. "You think Jim Edmonds, and you can't but help think of those great catches he made [in his career].
"So we were hoping he still had something left in the tank."
It turns out, Edmonds didn't. He hit .178 in 26 games and was released on May 9. He played better afterwards, with the Cubs and Brewers, but that didn't do the Padres or Towers much good.
But Edmonds' performance wasn't the part that bothered Towers the most -- it was, looking back on it now, giving up Freese.
"We had [third baseman] Kevin Kouzmanoff and Chase Headley coming, and he [Freese] was going to be blocked," Towers said. "We had the two young guys in front of him who we liked. We liked David, too.
"The lesson I learned from that was you don't trade guys just because you have depth at one spot."
This became more evident in 2011, when Freese, as the third baseman for the Cardinals, helped them win a World Series. More than that, he became just the sixth player in Major League history to be named MVP of a League Championship Series and the World Series.
Freese, a one-man wrecking crew, had a big league-record 21 RBIs during that postseason.
As for the 2011 Padres, they lost 91 games. Towers was long gone by then, too.
"That's the beauty of the game, you learn from your mistakes," Towers said. "Some deals you think are your better deals turn out to be your worst. Some of your worse deals become your best deals. Players change, there's injuries. So much changes."
One thing that did change, especially after the Freese deal, was how Towers looked at deals in terms of blocked players and depth at certain positions.
"Just because you're loaded with middle infielders doesn't mean you should shy away from drafting them," he said. "And corner infielders, like Freese, are hard to come by. I just thought, at the time, that he was expendable and we really liked Edmonds."