Re-hashing one of the worst Cubs offseason trades in franchise history

The history of the Chicago Cubs is full of missteps and decisions fans love to re-hash. The Lou Brock trade is the one most often recalled as a disaster of calamitous proportions, but the Dec. 1987 deal that sent future Cooperstown-bound reliever Lee Smith to the Boston Red Sox in exchange for a pair of back-end starters deserves its moment in the spotlight, as well.

On the heels of his All-Star 1987 campaign in which he notched his fourth-straight 30+ save season, Smith approached the Cubs front office about re-working and extending his deal with the team. He felt the work he'd done demanded more money and, frankly, he was right in the assumtpion.

“I never got the respect I thought a guy with those kind of numbers should have gotten,” Smith told the Chicago Tribune. “It had a lot to do with the broadcasters and who they played up. I was low key and I liked it like that."

Since making his big-league debut with the team in 1980, five years after Chicago took him in the second round of the 1975 MLB Draft, Smith had been a model of consistency in the late innings. The big right-hander piled up nearly 700 innings, pitching to a 2.92 ERA and 2.76 FIP, amassing 180 saves - all before turning 30.

Cubs short-changed Lee Smith in 1987 and it proved very costly

Instead of working out a new agreement with Smith, though, the Cubs traded him to Boston, acquiring the likes of Al Nipper and Calvin Schiraldi to shore up the rotation. That duo pitched parts of three seasons for Chicago, paling in comparison to what was yet to come for Smith.

Over the next decade, the Jamestown, LA native stacked up another 298 saves - and, to this day, he ranks third all-time with 478 total saves. He earned five All-Star selections in those 10 seasons, pitching for the Red Sox, Cardinals, Yankees, Orioles, Angels, Reds and Expos before calling it a career after the 1997 season at age 39.

The Cubs got a lot of good years from Smith, but looking back, it's clear he had plenty left in the tank and Chicago passed on some of the best seasons of his 18-year career for reasons that, to this day, feel pretty inexplicable and deserve mention among the worst offseason trades in MLB history.