Chicago Cubs: Looking back at impact offseason trades

February 25, 2015; Mesa, AZ, USA; Chicago Cubs president of baseball operations Theo Epstein during a spring training workout at Sloan Park. Mandatory Credit: Kyle Terada-USA TODAY Sports

The Chicago Cubs have seen some of their riskiest offseason trades pay off in big ways.

We’ve got three long months until we see some on-field baseball action. But this off-season promises to be one of the most exciting for the Cubs in quite some time.

They are expected to make plays for big money pitchers like David Price and Jordan Zimmermann, as well as being active in a number of trade talks involving their surplus of young position players.

Already, we’ve heard rumors of Starlin Castro being shipped to New York for the Yankees’ Brett Gardner as well as the Cubs sending a package including Javier Baez to the Braves for Julio Teheran or Shelby Miller.

Trades are exciting but risky–especially when they involve young prospects (like Baez). The Cubs will forever seem haunted by having traded away future Hall of Famer Lou Brock – even though that trade took place over 50 years ago.

We’ve seen other trades that found the Cubs on the losing side, like the Rafael Palmeiro deal.

The Cubs have made some amazingly good deals. Remember how they got Aramis Ramirez? Or the deal that netted them Jake Arrieta? Both those players came in midseason swaps… and the current Cubs regime of President of Baseball Operations Theo Epstein and General Manager Jed Hoyer have shown a knack for pulling off midseason deals.

But the Cubs have made some great off-season swaps, too. So let’s gird us for whatever the Cubs’ front office has in store for this off-season by revisiting the five best Cubs’ offseason trades of the recent past. (Sorry, we’re excluding anything outside the free agent period – it was just a different world back then.)

Next: A gritty leader and a speedster

Credit: Caylor Arnold-USA TODAY Sports

March 26, 1984: Cubs got Gary Matthews, Bob Dernier and Porfi Altamirano from the Philadelphia Phillies for Bill Campbell and Mike Diaz.

In 1984, the Cubs went to the playoffs for the first time in 39 years. Gary “Sarge” Matthews and Bobby Dernier were huge contributors to the Cubs post-season push.

Dernier provided the Cubs with a speedy leadoff presence and a steady glove in center field. He stole 45 bases while consistently getting on base in front of Cubs’ sluggers like Ryne Sandberg and Leon Durham. He was a half of Harry Caray’s “Daily Double” (alongside Sandberg), causing baserunning headaches for opposing pitchers and catchers. His efforts in center earned him a Gold Glove award.

Meanwhile, Matthews spent the majority of the season hitting in the three-spot in the Cubs lineup. He scored 101 runs that season and ended up fifth in MVP voting. “The Sarge” was a key clubhouse leader, bringing a winning attitude to a team that had known nothing but losing for a long, long time.

While neither of those players made a huge impact on the Cubs long-term, they meant a great deal to the ’84 team. While the players the Cubs sent over to Philadelphia were never missed in Chicago.

Next: Gearing up for a date with destiny

Credit: Jerry Lai-USA TODAY Sports

November 24, 2003: The Cubs got Derrek Lee from the Florida Marlins for Hee-Seop Choi and Mike Nannini.

Just a month prior to this trade, Derrek Lee, and the Florida Marlins had eliminated the Cubs in the National League Championship Series. They then did something typically Marlin-esque: they started unloading several of their key players. In this case, the Cubs were big beneficiaries.

More from Chicago Cubs News

• Cubs should keep close eye on non-tender candidate Cody Bellinger
• Cubs starting pitching has been thriving on the North Side
• Make no mistake: the Cubs are very much about power hitters
• Cubs: It’s time to start thinking about potential September call-ups
• Cubs: P.J. Higgins deserves to be in the lineup on a daily basis

At the time, parting ways with Hee-Seop Choi made some fans nervous. He was young. He had shown some flashes of being a decent first baseman.

And he was a fan favorite, having inspired his own unique cheer at Wrigley Field (“Hee! Seop! Choi!”) Lee had shown great success with the Marlins, but this was not a slam dunk deal.

By then end of the 2004 season, Lee had changed minds. He clubbed 32 homers, drove in 98 runs, and played great defense. He brought an extremely important aspect to the Cubs, too: plate discipline.

Surrounded by players like Sammy Sosa and Aramis Ramirez, who were not known for taking walks, Lee displayed a patience at the plate that began to change the Cubs “swing-first” mentality.

Lee’s best years came in a Cubs uniform. He played in two All-Star games, won two Gold Gloves as a Cub, and was a key contributor to Cubs’ playoff teams of the 2000’s. In the meantime, Nannini never played in the majors and Choi bounced around for two years before going back to play in his native South Korea.

Next: Slammin' Sammy comes to the Confines

March 30, 1992: The Cubs got Sammy Sosa from the Chicago White Sox for George Bell.

The Cubs were rebuilding in 1992. So just before the season began, new GM Larry Himes sent aging slugger George Bell across town to his former team, the White Sox, for a prospect Himes had long seen talent in but had seen little results from.

More from Cubbies Crib

• Cubs should keep close eye on non-tender candidate Cody Bellinger
• Cubs starting pitching has been thriving on the North Side
• Make no mistake: the Cubs are very much about power hitters
• Cubs are giving pitcher Javier Assad a deserved shot
• Cubs: It’s time to start thinking about potential September call-ups

Early returns appeared heavily in the White Sox favor: Bell drove in 112 runs for the Sox in 1992, while the player who came to the Cubs, Sammy Sosa, struggled to put all of his amazing tools together.

Sosa spent his first year with the Cubs moving from the bench on the big league club to Triple-A and back.

That was just a temporary condition.

By 1994, George Bell had retired and Sammy Sosa had 30/30 year under his belt (more than 30 home runs and 30 stolen bases) and was on his way to becoming the league’s premier power hitter.

While Sosa’s legacy is controversial due to suspected PED use and an acrimonious departure from the Cubs organization, it is a legacy marked by some amazing on-field accomplishments and many winning Cubs’ seasons.

Next: A lovable kid, a fearless slugger

Credit: Jerry Lai-USA TODAY Sports

January 7, 1982: The Cubs got Ryne Sandberg and Larry Bowa from the Philadelphia Phillies for Ivan de Jesus.

The crazy part of this deal: Larry Bowa was the centerpiece for the Cubs.

The Phillies had been unable to sign Bowa to a long-term deal. So they were looking to move their shortstop and found a willing partner in the Cubs, who coveted Bowa’s glove and leadership. The Cubs’ Ivan de Jesus was a good hitter for a shortstop, and the Phillies were excited about their return.

However, Cubs GM, Dallas Green, insisted on a prospect however and knew of Sandberg from his own days with Phillies. The Phillies’ scouts saw Sandberg as nothing more than a utility infielder, so the teams came to a deal.

The rest of this story needs little iteration: Sandberg found a home at second base, played in 10 All-Star games, won nine Gold Gloves, an MVP award, hit a then-record number of home runs for a second baseman (282, later surpassed by Jeff Kent) and was a first-ballot Hall of Fame-er.

De Jesus helped the Phillies get to the 1983 World Series, but ultimately dropped into obscurity… certainly without matching the numbers of Sandberg.

Next: One to stick it to the Cardinals

Oct 20, 2015; Chicago, IL, USA; A general view of outside Wrigley Field prior to game three of the NLCS between the Chicago Cubs and the New York Mets. Mandatory Credit: Aaron Doster-USA TODAY Sports

December 3, 1903: The Cubs got Mordecai Brown and Jack O’Neill from the St. Louis Cardinals for Larry McLean and Jack Taylor.

Here’s one honorable mention for the next time a Cardinals fan wants to remind you of the Lou Brock deal:

Mordecai “Three Finger” Brown was a six-time 20 game winner for the Cubs and the ace of the Cubs 1908 World Series championship team when he went 29-9.

He was elected to the Hall of Fame in 1949.

So we’ve got that going for us, Cubs fans… which is nice…