History of best/worst Cubs trades

With the annual MLB trade deadline of July 31st fast approaching, Cubs fans can be forgiven for dreaming of a thorough housecleaning by GM Jim Hendry and seeing Mike Quade’s roster retooled in the image of a team that could possibly win at least three games in a row – something the Cubs have yet to do after nearly four months of baseball futility.

But unlike fantasy baseball or youthful memories of trading bubblegum cards with your grade school pals, the Cubs will probably not make any blockbuster deals to change their miserable fortunes this season. The players management would like to move out are not particularly coveted by other teams and trading away what few quality players you have doesn’t make much sense.

There have been notable Cubs trades in the past, of course, good and bad alike. Let’s look at the five best and five worst Cubs trades over the past 50 years. 

#5 Worst Trade: RHP Burt Hooton

• June 8, 1971: Drafted by the Chicago Cubsin the 1st round(2nd pick) of the 1971 amateur draft (June Secondary).
• May 2, 1975: Traded by the Chicago Cubsto the Los Angeles Dodgersfor Eddie Solomonand Geoff Zahn. 

Less than a year after he was drafted out of college, Hooton pitched a no-hitter on a cold April Sunday at Wrigley Field against the Phillies. The blonde, baby-faced Texan’s out-pitch was his knuckle-curve, which sounds exactly like the combination of a curveball and a knuckleball that it was. It dropped down sharply, much like the split-finger fastballs of a later era. Hooton could also throw hard. 

Cubs coaches were not particularly enamored of Hooton’s “trick pitch” and wanted him to develop a more conventional repertoire. With the great starting staff of the late 60’s – early 70’s fading away (Jenkins, Holtzman, Hands, etc.), Hooton figured to be a front end of the rotation starter for the Cubs, along with Rick Reuschel, for many years to come. 

The trade to the Dodgers for a pair of decidedly mediocre pitchers made no sense and Hooton went on and continued to have a fine career with Los Angeles, reaching the postseason with them, something unachievable with the Cubs teams of that or any era. 

#5 Best Trade (2-way tie): First Baseman Derrek Lee

• November 25, 2003: Traded by the Florida Marlinsto the Chicago Cubsfor Mike Nannini(minors) and Hee-Seop Choi. 

GM Jim Hendry got a couple of gifts early in his tenure as Cubs general manager and acquiring Lee from the World Series champion Marlins for Choi, who would never succeed in the majors, was one such gift, the other being Aramis Ramirez (see below). The tall, lanky first baseman could be counted on to produce Billy Williams-like hitting numbers and his defense was non-pareil. A gentleman on and off the field and a quiet, dignified clubhouse presence, he didn’t receive the credit he deserved from Cubs fans during the Baker-Piniella years because of the team’s failure to win a pennant or World Series. But the ’69 Cubs are beloved – go figure! 

RHP Bill Hands and Catcher Randy Hundley.

• December 2, 1965: Traded by the San Francisco Giantswith Randy Hundleyto the Chicago Cubsfor Don Landrumand Lindy McDaniel. 

Speaking of those legendary ’69 Cubs, the trade to acquire starting pitcher Hands and his battery mate, Hundley, was one of a pair of deals which (almost) put Leo Durocher’s Cubs over the top. 

Hands was a workhorse for years, pitching up to 300 innings per season and winning 20 games in ’69. His out-pitch was the slider and the elbow strain of that particular pitch along with the old four man rotation grind, eventually wore him out before his time. 

Durocher could also be counted on to wear down his regular lineup and no one more so than Hundley who until he blew out his knee, was an All-Star catcher. The “Rebel” remains one of the old Cubs who appear at team functions and fans have apparently forgiven him for siring his son Todd, who became an Adam Dunn-like figure of frustration and derision by fans in his brief Cubs career after enjoying steroid fueled success with the Mets. 

#4 Worst Trade: RHP Dennis Eckersley 

• November 28, 1984: Signed as a Free Agent with the Chicago Cubs.
• April 3, 1987: Traded by the Chicago Cubswith Dan Rohnto the Oakland Athleticsfor Brian Guinn(minors), Dave Wilder(minors) and Mark Leonette(minors). 

Before Eck became a HOF closer for Tony LaRussa’s World Series teams in Oakland, he enjoyed a career as an excellent starting pitcher, both with Cleveland and Boston, and with a no-hitter to his credit. Unfortunately, by the time he reached the Cubs, he was at the nadir of his baseball career and personal life. He would eventually abandon the bottle and with the keen baseball sense of LaRussa and pitching coach Dave Duncan, still together in St. Louis, Eckersley became the game’s greatest 9th inning pitcher this side of Mariano Rivera. He did surrender Kirk Gibson’s famous limping walk-off homer in the 1988 World Series, but his prized mullet is bronzed in Cooperstown forevermore. 

#4 Best Trade: Third Baseman Aramis Ramirez

• July 23, 2003: Traded by the Pittsburgh Pirateswith Kenny Loftonand cash to the Chicago Cubsfor a player to be named later, Matt Bruback(minors) and Jose Hernandez. The Chicago Cubssent Bobby Hill(August 15, 2003) to the Pittsburgh Piratesto complete the trade. 

The second gift trade to Hendry was actually the first before Derrek Lee in 2004 (see above) and along with veteran centerfielder Lofton, Ramirez almost (a word always preceding any phrase having to do with a modern-day Cubs championship, sadly) helped Dusty Baker’s maiden Cubs voyage reach the World Series in ‘03. In his prime, Ramirez put up hitting numbers equal to any third baseman and he has been the Cubs best at that position since the late, great Ron Santo. 

Ramirez is playing his last days as a Cub, either to be traded soon or allowed to finish his career somewhere else after his contract is bought out after the season. Like D. Lee, Ramirez never got the Cubbie love he might have because of the team’s ultimate failures and for his own tendency to loaf, especially running the bases. 

#3 Worst Trade: First Baseman Rafael Palmeiro

• June 3, 1985: Drafted by the Chicago Cubsin the 1st round(22nd pick) of the 1985 amateur draft. Player signed June 11, 1985. December 5, 1988: Traded by the Chicago Cubswith Drew Halland Jamie Moyerto the Texas Rangersfor Luis Benitez(minors), Pablo Delgado(minors), Paul Kilgus, Curt Wilkerson, Mitch Williamsand Steve Wilson. 

In recent years, Palmeiro has been justly scorned as a steroid cheat and finger wagging, public liar to Congress (why then, does he not hold elected office?). In the late 80’s, it was thought the Cubs could not keep both Mark Grace and Raffie, both left handed hitting first basemen (although early in his career, Palmeiro did play outfield) and one had to go. 

So, the only man to hit over 500 HRs and have 3,000 hits and not be elected to the HOF went to Texas in exchange for Mitch “Wild Thing” Williams who enjoyed one memorable year for the Cubs as their closer for Don Zimmer’s ’89 division winners, but eventually would join the Phillies and serve up Joe Carter’s (another traded ex-Cub – see below) walk-off World Series winning home run in ’93. Williams’ current career as an ESPN baseball analyst is proof that the media want to find the second coming of Terry Bradshaw. Why there is a need for another Bradshaw is as confounding as the popularity of NASCAR. 

#3 Best Trade: Outfielder Sammy Sosa

• March 30, 1992: Traded by the Chicago White Soxwith Ken Pattersonto the Chicago Cubsfor George Bell. 

In order to fully appreciate Sosa’s amazing career and life arc, one has to somehow wed the cinematic sensations of "A Star Is Born" and "Scarface" with "Baseball" documentarian, Ken Burns’ sentimental romanticism. 

Sammy became the most famous Cubs player since Ernie Banks and before his Icarus-like fall, he was as attached to the franchise as Mr. Cub. The 1998 season was turned by filmmaker Burns into a sort of baseball Camelot in his recent "Tenth Inning" documentary, but the reality today is that while even Barry Bonds and Mark McGwire still have their blindly loyal fans in San Francisco and St. Louis, respectively, Chicago holds no warm spot for an athlete who only was eclipsed in his professional hometown by Michael Jordan. 

Aside from a tiny pennant bearing the number 66 (HRs hit in '98) flying atop the roof of Wrigley Field, Sosa is as expunged in Cubs lore as Josef Stalin was in Soviet Russia. Unsure whether to admire Cubs fans for their lack of denial or criticize them for their hypocritical heartlessness in abandoning their fallen hero. 

#2 Worst Trade: RHP Lee Smith

• June 3, 1975: Drafted by the Chicago Cubsin the 2nd roundof the 1975 amateur draft. Player signed June 20, 1975.
• December 8, 1987: Traded by the Chicago Cubsto the Boston Red Soxfor Al Nipperand Calvin Schiraldi. 

After trading HOF reliever Bruce Sutter, the Cubs had to go a few years without a top-notch closer until Smith filled the void in the mid-80’s. His huge presence belied an amiable nature, but opposing batters remained scared of his overpowering fastball and heavy sinker. 

After the oh-so-close ’84 team crumbled into the disastrous ’85 and ’86 campaigns, the drumbeat was loud to get rid of Smith whom fans began to particularly associate with those failed seasons. A trade to Boston resulted in the Cubs receiving a Red Sox World Series goat in Schiraldi and a cipher in Nipper while Smith went on to compile the third most career saves in MLB history with several different clubs. 

#2 Best Trade: RHP Ferguson Jenkins

• April 21, 1966: Traded by the Philadelphia Phillieswith John Herrnsteinand Adolfo Phillipsto the Chicago Cubsfor Bob Buhland Larry Jackson.
• October 25, 1973: Traded by the Chicago Cubsto the Texas Rangersfor Vic Harrisand Bill Madlock. 

A coup for then Cubs GM John Holland, who along with Dallas Green in the 80’s and current GM Jim Hendry, comprise the top three general managers in recent team history, the trade to acquire future Hall of Famer Jenkins, the only pitcher in MLB history to have less than 1,000 walks to go along with over 3,000 strikeouts and winner of 20 or more games in 7 out of 8 consecutive seasons (6 straight from ’67-’72 with the Cubs) almost offsets Brock for Broglio (see below). 

His trade to Texas resulted in Fergie winning 25 games in his maiden season as a Ranger, but the Cubs got a batting champion in return in the form of third baseman Madlock. Like several other African American ballplayers who refused to live up to Ernie Banks-like congeniality, the Cubs traded away another talented black ballplayer in Mad Dog for the more palatable Bobby Murcer after the ’76 season. Jenkins has since returned to the Cubbie fold, both he and Greg Maddux sharing the honor of having their respective #31 jerseys retired. 

#1 Worst Trade: Outfielder Lou Brock

• August 22, 1960: Signed by the Chicago Cubsas an amateur free agent.
• June 15, 1964: Traded by the Chicago Cubswith Jack Springand Paul Tothto the St. Louis Cardinalsfor Ernie Broglio, Doug Clemensand Bobby Shantz. 

What commonly stands for the all-time worst trade in baseball history this side of the Curse of the Bambino, Brock went from frustrated Cub to a HOF career with the Cardinals, helping St. Louis win three pennants and two World Series over the next four years after he left Chicago. 

It’s uncertain if Brock would have ever developed into the all around hitter and greatest base stealer since Ty Cobb (Brock held the SB record until Rickey Henderson) had he remained a Cub. It’s hard to imagine the 60’s Cardinals without him or even the 60’s Cubs with him, but as sports trades in Chicago go, it wasn’t the worst. The Blackhawks trade of Phil Esposito, Ken Hodge and Fred Stanfield to the Bruins was even more catastrophic, if one allows for comparing sports apples and oranges. 

#1 Best Trade: Second Baseman Ryne Sandberg

• January 27, 1982: Traded by the Philadelphia Phillieswith Larry Bowato the Chicago Cubsfor Ivan de Jesus. 

Bombastic and blustering GM Dallas Green tried to remake the Cubs in his own championship Phillies image and nearly pulled it off with a number of acquisitions from his former team, the Sandberg trade being, of course, the coup dé grace. 

Sandberg started out as slowly as did Willie Mays in his rookie season, but eventually became perhaps baseball’s greatest second baseman and carried himself with a shy dignity alá Lou Gehrig. Cubs fans should be grateful he did not inherit the managerial job he so coveted this past off-season and have to suffer the indignity of the 2011 Cubs, but perhaps Ryno will eventually return to his baseball home and, fittingly, bring the North Siders their long overdue World Series championship someday. 

And a few other deals of note: 

Draft dodging: Bill Stoneman RHP

• October 14, 1968: Drafted by the Montreal Exposfrom the Chicago Cubsas the 19th pick in the 1968 expansion draft.

Stoneman was little used by the Cubs, but became a #1 starting pitcher for the expansion Montreal Expos in 1969, pitching a no-hitter in April enroute to an 11-19 record that season with over 200 innings pitched. Not bad, considering the Expos lost more than 100 games their first year.

Stoneman had several more decent seasons in Canada and had he remained a Cub and been their fourth starter in ’69, he might well have won 15 games or more. That itself, could have been enough to hold off the Amazin’ Mets and rewrite Cubbie history.

Money Well Spent: Milt Pappas

• June 23, 1970: Purchased by the Chicago Cubsfrom the Atlanta Braves.

The Cubs did get that much needed starting pitcher the following year and the veteran Pappas, who won 100 games in each league, finished out his fine career as a Cub, winning 17 games in both ’71 and ’72. His near perfect game in September of ’72 has made umpire Bruce Froemming an immortal Cub villain all these years.

Everybody Loses: Ron Santo

• December 11, 1973: Traded by the Chicago Cubsto the Chicago White Soxfor a player to be named later, Ken Frailing, Steve Stoneand Steve Swisher. The Chicago White Soxsent Jim Kremmel(December 18, 1973) to the Chicago Cubsto complete the trade.

Santo spent one miserable year on the South Side which prematurely ended what eventually will turn out to be a Hall of Fame career, albeit posthumously awarded. Ronny felt betrayed as the Cubs were breaking up that old ’69 gang, all of whom, with the exception of Banks, not being allowed to finish their careers as Cubs (although Jenkins and Holtzman came back for curtain calls).

The estrangement between Santo and old Cubs management lingered for a long time until he finally came back home as a broadcaster and beloved team mascot after over a decade away from Wrigley Field. Steve Stone also became a long time Cubs broadcaster, but was never beloved. Instead, he parlayed his one remarkable Cy Young Award winning season with the Orioles into a media career notable for its charmless arrogance and smugness.

Everybody Wins: Rick Sutcliffe

• June 13, 1984: Traded by the Cleveland Indianswith George Frazierand Ron Hasseyto the Chicago Cubsfor Darryl Banks(minors), Joe Carter, Mel Halland Don Schulze.

Sutcliffe’s arrival in 1984 at mid-season secured the team their first postseason appearance since 1945. His 16-1 Cubs record that year earned him a Cy Young Award, but not even Sutcliffe could overcome Leon Durham’s Gatorade soaked glove in Game 5 of the NLCS against San Diego.

Injuring his hamstring the next season, Sutcliffe came back too soon to pitch and wound up hurting his arm. He never pitched as well again for the Cubs and became a national broadcaster while fighting his health battles versus cancer and alcoholism.

Joe Carter also became a Cubs broadcaster, however briefly. Before that, he enjoyed an outstanding playing career, first with the Indians and later with the Blue Jays, helping Toronto win back-to-back World Series titles and becoming only the second man to win a World Series with a walk-off home run.

Love Me Two Times: Rick Monday

• January 11, 1977: Traded by the Chicago Cubs with Mike Garman to the Los Angeles Dodgers for Jeff Albert (minors), Bill Buckner and Ivan de Jesus. 

After becoming baseball's first amateur draft pick in 1965, Monday just missed out on playing for the Oakland dynasty teams '72-'74 after being traded to the Cubs. Holtzman's career rebounded pitching for the A's in their spacious stadium and he collected the World Series rings. Monday would memorably save an American flag from being burned on the field at Dodger Stadium during a game in 1976.

The all-around excellent centerfielder was later traded to the Dodgers where he remains as a broadcaster. DeJesus and Buckner both played well for the Cubs with the former shortstop now a coach for Mike Quade while Buckner became baseball's biggest scapgoat since Fred Merkle for his World Series error for the Red Sox in '86. An unjust coda to a fine career, Buckner has slowly shed the skin of that infamy, but seemingly will never quite leave that night in Game 6 for as long as he lives.