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11 Best Trades In Chicago History

Twenty-five years ago today, a Chicago team traded for arguably the best second banana in the history of professional sports. To honor the anniversary of that wonderfully one-sided deal, let’s see where that swap lands on our list of the 11 best trades in Chicago history.

11) Hank Borowy (1945)

TRADE: Cubs acquire Hank Borowy from the Yankees for $97,000. The Cubs got the right-hander in July, and he went 11-2 the rest of the way to help clinch what remains the team’s last pennant. Just as noteworthy was Borowy’s trade out of Chicago three years later. He was sent to Philadelphia with Eddie Waitkus, who had been stalked by a disturbed woman while a Cub. When Waitkus returned to Chicago, she shot and nearly killed him at a North Side hotel. The story inspired the Bernard Malamud book and sepia-toned Robert Redford flick, “The Natural.”

10) Ozzie (1984)

TRADE: White Sox acquire Ozzie Guillen, Tim Lollar, Bill Long, and Luis Salazar from the San Diego Padres for LaMarr Hoyt and two minor leaguers. Eyebrows were raised when the Sox traded Hoyt—just one year removed from his Cy Young Award—for a skinny Venezuelan shortstop. Sox GM Roland Hemond made the deal on the recommendation of scout Jerry Krause (yes, that Jerry Krause). Hoyt pitched just two seasons in San Diego before injuries and drug issues caught up to him. Meanwhile, Guillen was the American League Rookie of the Year in 1985, made three All-Star teams, and enjoyed eight colorful seasons as Sox manager that included a World Series title.

9) Lofton, Aramis (2003)

TRADE: Cubs acquire Kenny Lofton and Aramis Ramirez from the Pittsburgh Pirates for Jose Hernandez, Matt Bruback, and a player to be named later. After Corey Patterson (shudder) was lost for the season in July, Cubs general manager Jim Hendry made one of the best moves of his tenure, landing Lofton and Ramirez to energize a North Side playoff run. Said Sammy Sosa at the time: “I think it’s awesome.” He was right. Lofton sparked the Cubs at the top of the lineup, hitting .327 in 56 games. Ramirez hit 15 homers in 63 games and turned into the Cubs’ best third basemen since Ron Santo. Hernandez was never more than a utility man for the Pirates.

8) Paulie (1999)

TRADE: White Sox acquire Paul Konerko from the Cincinnati Reds for Mike Cameron. At the time, it was a trade of two promising youngsters who hadn’t panned out. The talented Cameron hit .210 for the Sox in 1998, so White Sox GM Ron Schueler shipped him to Cincinnati for Konerko, who hadn’t hit higher than .219 in his two big league seasons. Cameron hit a serviceable 221 homers between 2000 and 2009. All Konerko has done is hit more than 400 homers (plus a grand slam in Game 2 of the 2005 World Series) and become a South Side work of art.

7) Fergie (1966)

TRADE: Cubs acquire Ferguson Jenkins, John Herrnstein, and Adolfo Phillips from the Philadelphia Phillies for Bob Buhl and Larry Jackson. Just three weeks into the 1966 season, the Cubs sent two aging pitchers east in exchange for the 24-year-old from Ontario. Jenkins won at least 20 games between 1967 and 1972, including the 1971 Cy Young season when he went 24-13 with a 2.77 ERA. Jackson won 41 games in three seasons for the Phillies. Buhl won six. Today, Fergie has a plaque in the Hall of Fame—the first Canadian to be immortalized at Cooperstown.

6) Ryno (1982)

TRADE: Cubs acquire Ryne Sandberg and Larry Bowa from Philadelphia Phillies for Ivan De Jesus. Dallas Green wanted a veteran presence in the locker room when he reached back to his Philadelphia roots and grabbed Bowa, who started at shortstop for the Cubs for three and a half seasons. The bigger coup, of course, was Sandberg, a farmhand tossed in for good measure. In 1983, Sandberg switched to second base and went on to a Hall of Fame career with 282 homers and an MVP award for his awesome 1984 season. De Jesus hit 51 homers over his first three years in Philadelphia, but only five over the next four injury-riddled years.

5) Nellie Fox (1949)

TRADE: White Sox acquire Nellie Fox from the Philadelphia Athletics for Joe Tipton. The second baseman famous for a cheek full of tobacco led the White Sox’ resurgence of the 1950s that culminated in the 1959 pennant. He teamed with shortstop Luis Aparicio to spearhead the “Go-Go Sox,” appeared in 12 All-Star games, and was the American League MVP in 1959. In 14 seasons with the Sox, he had 2,470 hits and two Gold Glove awards. Fox was voted into the Hall of Fame in 1997. Meanwhile, Tipton was out of baseball by 1955.

4) The Danimal (1978)

TRADE: The Bears send Wally Chambers to the Tampa Bay Buccaneers for a draft pick. After the 1978 season, the Bears traded Chambers, a defensive lineman and three-time Pro Bowler, in exchange for the fourth pick of the 1979 draft. The Bears drafted Hampton out of Arkansas with the pick. In 12 seasons with the Bears, Hampton was an anchor on the 1985 Super Bowl team, made four Pro Bowls, and manged 60 sacks. Buddy Ryan later called The Danimal “the cornerstone of the 46 Defense,” and Hampton is now enshrined in the Hall of Fame. Chambers played just two seasons in Tampa Bay, undone by bad knees.

3) Glenn “Mr. Goalie” Hall (1957)

TRADE: Hawks acquire Glenn Hall and Ted Lindsay from Detroit Red Wings for Hank Bassen, Forbes Kennedy, Bill Preston, and Johnny Wilson. The lineage of great Blackhawks goalies that includes Tony Esposito, Ed Belfour, and Dominik Hasek began with Hall, who had a 2.51 GAA in the Hawks Stanley Cup year of 1961. That season, he led the NHL in games played, minutes played, shutouts, and was named to the NHL Second All-Star team. Hall was a mainstay between the pipes for 10 years at Chicago Stadium, while none of the four players sent to Detroit made an impact.

2) Sammy (1992)

TRADE: Cubs acquire Sammy Sosa and Ken Patterson from White Sox for George Bell, 1992. Steroids or not, Sosa was the darling of Wrigleyville and a huge producer for the better part of his North Side stay. His 545 homers as a Cub still count, as do the two trips to the postseason that wouldn’t have happened without Slammin’ Sammy. Bell did pace the Sox with 25 homers in 1992, but was a jerk in the clubhouse (he once said he didn’t respect skipper Gene Lamont “as a manager or a man”), and the Sox dumped him the day after they lost the 1993 ALCS. Ironically, a Tribune headline the day after the trade read, “Blockbuster Deal a Bell-Ringer: Cubs Like Sosa’s Outfield Defense.”

1) Pippen (1987)


TRADE: Twenty-five years ago today—on NBA draft day, 1987—the Bulls sent Olden Polynice and some future draft detritus to Seattle for Scottie Pippen. Jerry Krause not only nabbed Pippen, the 6-foot-7 forward and fifth pick out of Central Arkansas, but also chose Horace Grant from Clemson with the 10th pick. “With a little kick of his heels and big grin on his face, Jerry Krause was practically walking on air as he met the press Monday,” Tribune scribe Bob Sakamoto wrote the day after the draft. Four years later, the Bulls were champs. Polynice, selected eighth, had a serviceable NBA career, but serviceable doesn’t win six championships.

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DANIEL I. DORFMAN is a freelance sportswriter living in Chicago.

STORY ART: Main image made in-house with Getty Images photo. Ozzie photo courtesy Rafael Amado Deras/cc; Hendry photo courtesy delusionalcubsfan/cc; Sosa photo courtesy Barbara Moore/cc.

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