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The 10 Greatest Trades In Cubs History

The Cubs have made a lot of trades. Some bad. Some good. These are the best.

Jonathan Daniel/Getty Images

Eleven years ago today, the Cubs traded a young, promising first baseman named Hee-Seop Choi to the Florida Marlins for Derrek Lee. At the time, the move was somewhat controversial, as Choi was both a fan favorite and a sabermetric darling. No one doubted Lee's ability, but the deal was seen as a sign that the Cubs (and Dusty Baker in particular) wouldn't give young players a chance.

I don't need to tell you how that one turned out. Choi showed flashes of promise in Florida and Los Angeles, but he was never able to establish himself as a major league regular and eventually went back to Korea to play. Lee was a two-time All-Star with the Cubs and lead the team to two division titles.

In any case, that got me to thinking. Is that one of the greatest Cubs trades of all time? Cubs history goes back a long ways and there have been a lot of trades. Does Lee make the top ten?

So I went over to and went through every trade the Cubs ever made. I tossed out outright purchases--before World War II it was quite common for teams to just sell players rather than trade them. So maybe I should have counted them. But it seems that in a purely baseball sense, there is little risk to buying a player.

I looked at both what the Cubs got, what the Cubs gave up and the situation that the Cubs were in. I certainly looked at WAR figures, but I'm not ranking them on a purely statistical basis. This list is subjective. You're welcome to make your own list if you disagree.

We can all hope that the Jeff Samardzija or Matt Garza trades end up on this list one day, but Choi shows the folly of counting your prospects before they hatch.

One thing I learned from this list. The Cubs should mainly trade with teams from Pennsylvania.

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

When Dallas Green came over from the Phillies to become the Cubs GM, he made a series of trades with his old team where he plundered the system for players that he knew were better than the Phillies thought they were. More on that later. But coming out of spring training in 1984, the Cubs made one last adjustment to their roster when they picked up Matthews and Dernier, solidifying their outfield. Both Dernier and Matthews were only good for one season with the Cubs, but without the two of them the Cubs don't win their first title of any sort in 39 years.

Campbell was a veteran reliever who had signed with the Cubs as a free agent in 1982. He would have three more decent seasons as a middle reliever for the Phillies, Cardinals and Tigers before a short stint with the Expos and retirement. Diaz would eventually have one OK season for the Pirates, but that was about it.

9. June 13, 1984. The Cubs acquire Rick Sutcliffe, George Frazier and Ron Hassey from the Indians for Joe Carter, Mel Hall, Don Schultze and Darryl Banks.

This is the one trade on the list that the team on the other end wouldn't take back. It was a classic "win-now" move at the trade deadline where the Cubs gave up the future for a chance the present. It's also the only trade on the list where the Cubs gave up more, in terms of WAR at least, than they got back. Although one could argue that dumping Mel Hall (who would commit a series of sex crimes over the next 25 years) was worth it in the long run. When the Cubs acquired Dernier and Matthews, that meant they had no room in the outfield for Hall and Carter. So dealing them in a "win-now" move made a lot of sense.

Sutcliffe went 16-1 down the stretch for the Cubs. Frazier and Hassey weren't much, but giving up Joe Carter's career for a trip to the playoffs was probably worth it. It certainly would have been worth it if Leon Durham caught that ball. Sutcliffe would re-sign with the Cubs as a free agent at the end of the year and would alternate between being good and being injured for the Cubs until he left as a free agent after the 1991 season.

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

I already covered this one in the introduction and in my mind it is indeed one of the ten greatest trades in Cubs history. Lee played seven seasons for the Cubs and had a career WAR of 22.5 with the Cubs. It's also a lesson that teams should not get too attached to their prospects.

7. July 23, 2003. The Cubs acquire Aramis Ramirez and Kenny Lofton from the Pittsburgh Pirates for Jose Hernandez, Bobby Hill and Matt Bruback.

Before the Cubs got Ramirez, whenever anyone talked about Cubs third basemen, it was always preceded by "The Cubs haven't had a third baseman to do _______ since Ron Santo retired." Ramirez would be the Cubs third baseman for the next nine seasons and make two All-Star teams. Lofton gave them a center fielder and leadoff hitter that they needed when Corey Patterson went down for the season with a knee injury. (And he was better than Patterson, as you all know.)

Not only that, but they gave up nothing. Hill was a bust. Hernandez was through as a regular and Matt Bruback never made the majors.

6. December 11, 1917. The Cubs acquire Pete Alexander from the Phillies for Pickles Dillhoefer, Mike Prendergast and cash.

Always trade with Pennsylvania. The Phillies are somewhat excused from this one as Alexander was joining the Army and would spend most of the 1918 season fighting the Kaiser. The Phillies wanted to get something for him (and the money was the most important factor) so they took what they could get. No one even knew if there would be a 1919 season at the time.

But of course there was a 1919 season and Alexander would go on to be the Cubs ace for nine seasons. While he was never quite as good with the Cubs as he was in  his youth with the Phillies, he was still plenty good.

5. November 27, 1927. The Cubs acquire Kiki Cuyler from the Pirates for Sparky Adams and Pete Scott.

Cuyler was one of the best outfielders in the National League with the Pirates and he was in his prime: a 4 to 6 WAR player. He regularly led the National League in steals. But he didn't get along with Bucs manager Donie Bush, who benched him for half a season, including the 1927 World Series. The Cubs took a chance on this troublemaker and got a Hall of Famer in his prime who would lead the team to two pennants.

Adams was a serviceable second baseman/utility infielder, but nothing special. Scott played 40 games for the Pirates.

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

On WAR alone, this trade should be two spots higher but I knocked it down a bit because it's Sammy. But new Cubs GM Larry Himes loved Sosa. He traded for him from Texas when he was the White Sox GM, and he was going to get him again.

Bell had been the Cubs big free agent signing before the 1991 season after an impressive career with the Blue Jays, albeit one that was highly overrated because of that era's obsession with the RBI statistic. He was solid in 1991 with the Cubs, hitting .285 with 25 home runs, but the Cubs got rid him right on time. He was pretty mediocre with the White Sox. He'd play two seasons before retiring after the White Sox played in the 1993 ALCS. He sat on the bench the whole series.

I still remember talking to a White Sox fan after the 1992 season where he teased me about the Cubs giving up George Bell for Sammy Sosa. My comment then was "just wait." I was right in so many ways.

3. April 21, 1966. The Cubs acquire Ferguson Jenkins, John Herrnstein and Adolfo Phillips from the Philadelphia Phillies for Bob Buhl and Larry Jackson.

Once again, the Cubs trade with a Pennsylvania team and get a Hall of Famer. The Phillies still thought of themselves as a contender going into the 1966 season, and the lesson of their 1964 collapse is that they didn't have enough starting pitching. But trading for pitching on the wrong side of 35 is always a dubious proposition. Buhl was pretty much finished, although Jackson did give them three solid seasons. But the Phillies only won two more games in 1996 than they had in 1965.

Jenkins would pitch the next eight seasons for the Cubs. He would win 20 games six times and win the Cy Young Award in 1971. He even provided value on the backside as when he turned 30, the Cubs shipped him off to Texas for Bill Madlock.

To add insult to injury, Phillips would end up being a solid center fielder for three years and a very good one in 1967, even if he and Leo Durocher didn't get along. Phillips got hit by a pitch in 1968 and missed time with an injury that Durocher said he was faking. That was the end of his productive time in Chicago.

2. December 3, 1903. The Cubs acquire Mordecai Brown and Jack O'Neill from the St. Louis Cardinals for Larry McLean and Jack Taylor.

The next time a Cardinals-fan co-worker brings up Brock-for-Broglio, just shoot back with Brown for MacLean and Taylor. Yeah, that's not going to work. Sorry. Don't try it.

But in reality, Miner Brown (I won't call him "Three-Finger." That's what the New York newspapers called him, not his friends.) was a far better player than Lou Brock ever was. Along with Christy Mathewson, Brown was one of the best two pitchers of the first decade of the 20th century. He led the Cubs to four pennants and two World Series titles. Not only was he the best Cubs starter, he was their best reliever as well as he would often come in to finish out games on the days he didn't start. It was a different time back then to be sure, but the Cubs have still never had a better pitcher than Miner Brown.

Taylor was actually a decent pitcher and he did win 20 games for the Cardinals in 1904. But again, he was on the wrong side of 30 and the Cardinals would trade him back to the Cubs for their 1906 and 1907 pennant winners.

McLean would eventually have a long career as a catcher, but not for the Cardinals who would sell him to Cincinnati.

1. January 27, 1982. The Cubs acquire Larry Bowa and Ryne Sandberg from the Philadelphia Phillies for Ivan DeJesus.

When this trade was announced, it was Bowa for DeJesus. Sandberg was the throw-in. Bowa was an aging shortstop who had worn out his welcome in Philadelphia (surprise, surprise) and whose defensive ability didn't match his reputation at the time, which was based on his stellar fielding percentage. It's hard to make a lot of errors when you don't get to anything that's not right in front of you. DeJesus had been a promising young shortstop for the Cubs in the late-70s, but he had a miserable season in 1981 and he wasn't Dallas Green's type of player anyway.

Sandberg, of course, was why you should never trade with a team that knows your system better than you do. You wonder if the Padres won't regret allowing Jed Hoyer to take Anthony Rizzo with him to Chicago. Maybe that trade will end up on this list in 25 years. But for today, the Cubs stealing a Hall of Fame second baseman who would play 16 seasons in Chicago ranks as number one on this list.

And if the Cubs acquire Cole Hamels from Philadelphia? From history, I like the odds of that deal turning out nicely.