Chicago Cubs: Ranking the team’s 3 worst trades of the last 50 years

Cubs: 3 worst trades of the last 50 years: #1 – Future HOF closer Lee Smith gets sent to the Red Sox after requesting a trade in 1987

Lee Smith ranks among the best closers in baseball history – but that didn’t stop the Cubs from fulfilling his trade request and sending him to Boston in a deal that netted reliever Calvin Schiraldi and starting pitcher Al Nipper.

Nipper pitched just one season on the North Side and was pretty unremarkable – so much so, Chicago cut ties with the right-hander at the end of the 1988 campaign. His career lasted just two more seasons – which tells you all you need to know about any sort of ‘value’ the Cubs got in this return.

Meanwhile, Schiraldi lasted a whopping two seasons before the Cubs traded him to San Diego. All this to say, these two pitchers came nowhere near the production Smith had for the rest of his career. By the time the right-hander hung up his spikes, he racked up another 298 saves, making 564 appearances en route to a Cooperstown-worthy resume.

Honorable Mention: Eloy Jimenez, Dylan Cease traded to the South Side

Even just five years later, this trade doesn’t look good. Yes, the Cubs desperately needed controllable starting pitching, but at what cost? Jimenez has the potential to be one of the best offensive presences in the league and Dylan Cease is coming off a breakout 2021 season.

Quintana took the ball every five days, but it’s pretty clear Epstein overpaid to get this deal done, hoping to light a fire under the reigning World Series champs. It’s hard to lump this in with the other trades mentioned here, but it has all the makings of one of those trades that just looks worse as more time passes.