#1 Worst: Cubs Acquire Ernie Broglio from St. Louis for Lou Brock
There's a reason why we keep beating this dead horse. Lou Brock for Ernie Broglio is so infamously bad it has its own Wikipedia page dedicated to it. It still haunts the Cubs in many ways to this day. While there were other players involved in this deal, it was only Broglio and Brock that truly mattered in the grand scheme of things.
Before the 1964 deadline, the Cubs would make the ultimate blunder by trading for Broglio and sending Brock along with two other players in the package deal. It seemed like a steal at the time since Broglio had come off multiple successful seasons in St. Louis. As it was later revealed, however, Broglio had dealt with a shoulder injury in 1963 that eventually required more work in November of 1964. He'd post a pedestrian 4.04 ERA in the 100 1/3 innings after the deal, but after that, the wheels would fully come off as he'd only pitch two more seasons and post a 6.61 ERA across only 113 innings.
Brock, meanwhile, could have his own chapter in the Cardinals' history book. In St. Louis, he'd eclipse 3,000 hits, become the all-time stolen base leader (until Rickey Henderson came along), make the NL All-Star team six times, make the Hall of Fame, and help the Redbirds to not one, but two World Series wins including 1964. For two and a half miserable years of Broglio, they received 15 1/2 incredible years of Brock. It was clear the Cubs weren't utilizing Brock's skills correctly, but the results of this trade are mind-bogglingly bad nonetheless.