Chicago Cubs: Worst Player Personnel Moves in Team History
The Chicago Cubs organization has made its fair share of questionable roster decisions in the past.
There have been mind-boggling trades and head-scratching free agent signings to go along with decisions to not re-sign talented players.
One of the many proclamations Theo Epstein and Jed Hoyer have made since coming to the North Side is their intention to not offer any more contracts with a no-trade clause. Ryan Dempster and Alfonso Soriano would be relevant examples why, but they both were 5/10 players.
The reason for not offering no-trade clauses is to avoid having player contracts hinder the club’s plans at any future point.
Not all team-detrimental contracts have a no-trade clause, however. Some are for six, seven, or eight years; or both long and no-trade. Then there are some contracts that are for only one or two years and also shoot an organization in the foot.
But bad contracts are not the only way a club can get in the way of their own future.
There are trades that leave you wondering if the owner or general manager was liquored up when they made the move.
Then there are decisions to let a player pursue free agency when the organization believes he's past his prime—Boston Red Sox/Roger Clemens, 1996.
This list is a review of the top ten worst roster moves in Chicago Cubs history. (Watch for a future article profiling the top ten best roster moves in club history.)
10. April 3, 1987: Dennis Eckersley Traded to Oakland Athletics
The Dennis Eckersley trade sits at the No. 10 spot because Eckersley’s career up to that point showed no indication of him becoming one of the most dominant relief pitchers in baseball history.
As a starting pitcher, Eckersley was good in his first one-and-a-half seasons with the Cubs. But in 1986 he posted a 6-11 record with a 4.57 ERA.
Eck battled alcoholism through his career, and it was not until after the 1986 season, the worst of his career, that he sought treatment.
That offseason the Cubs dealt Eck to the Oakland Athletics, who were managed at the time by Tony La Russa.
The budding baseball genius La Russa moved his acquisition into the closer’s role after two starts by Eck and an injury to then-closer Jay Howell.
After posting 16 saves in 1987, Eck went on to record 45 in 1988 and become one of the most dominant relief pitchers in baseball history, earning himself election into the Baseball Hall of Fame in 2004.
9. Danny Jackson Signed to a 4-Year, $10.55 Million Contract
Danny Jackson was the headliner in the Cubs’ ill-fated 1991 free agent acquisitions, after helping bring a World Series to the Queen City.
Giving Jackson a contract that paid him roughly $2.6 million per season, the Cubs expected him to be a good accent piece to a rotation that already sported Greg Maddux and Rick Sutcliffe.
Unfortunately for the Cubs and Jackson, the plan did not go…well…as planned.
In his first season with Chicago, Danny went 1-5 with a 6.75 ERA, racking up more bases on balls than strikeouts.
The following season, 1992, he was unceremoniously traded to Pittsburgh for Steve Buechele. Following the 1992 season he was drafted by the Florida Marlins in the expansion draft, then traded to the Philadelphia Phillies for Joel Adamson and Matt Whisenant.
8. LaTroy Hawkins Signed to a 3-Year, $12 Million Contract
I can still see it now, or rather, hear it. Sitting in field box 12, aisle 131, row 5, seat 5, I can still hear the crack of a ball from a line drive off the bat of Brad Hawpe crashing against the elbow of Mark Prior in the fourth inning, louder than when the ball initially hit the bat.
Then after minutes of stunned silence while all Cubs fans held their breath as if oxygen levels were in low supply, the young pitcher was helped off of the field.
Even though the Cubs responded by scoring four runs in their half of the fourth and later five more, my prayers were still sent up to the heavens asking the Almighty to bless Mark Prior with a speedy recovery and to keep LaTroy Hawkins out of the game.
But to no avail.
Cubs fans still remember the torment of seeing Dusty Baker continue to trot LaTroy Hawkins to seemingly blow save after save…after save…after save in 2005.
LaTroy earned his pay in 2004, going 5-4 with a 2.63 ERA along with 25 saves in 77 appearances, though he did have nine blown saves.
But in 2005 the Cubs needed to see him amass four converted—and many blown—saves in only 21 appearances before they knew it was time to cut their losses. One of the best decisions in the Jim Hendry era was to clean up one of the worst.
7. Jeff Blauser Signed to a 2-Year, $8.2 Million Contract
Jeff Blauser’s signing is another example of a club rewarding a player with a contract, based on one season’s performance.
Blauser had a solid career in Atlanta, but subtract his contract year and his last three seasons with the Braves would not have justified giving him such a high-value contract.
If the Atlanta Braves had given him the same contract as the Cubs, it would not have been such a bad decision—a “we appreciate your 11 years of service so we’re going to give you this contract to show our gratitude” type of contract.
6. Todd Hundley Signed to a 4-Year, $23.5 Million Contract
Signing Todd Hundley to such a bad contract was a blessing in disguise.
Randy Hundley earned Todd this horrible contract with the Cubs. Randy Hundley, Todd’s father, was one of the most beloved Cubs in the 1960s and 1970s.
Randy has been labeled as possibly the greatest Cubs catcher of all time. His son was just as good, if not better with more power. So why shouldn’t the Cubs give him a contract that paid almost $6 million per year?
When the Cubs decided to sign Todd, he was already a two-time All-Star. He set a league record for home runs by a catcher with 41 in 1996, followed that with 30 in 1997 (both seasons with the Mets) and hit 24 HR in both seasons with the Dodgers before signing with Chicago.
Regretfully for the Cubs, they again signed a once-accomplished player on the way out.
In his two seasons with the Cubbies, Hundley had a line of .199/.285/.398, with a total of 28 HR, 66 RBI, and 169 strikeouts, before being dealt back to Los Angeles for Mark Grudzielanek and Eric Karros on December 4, 2002. And therein lies the blessing.
Maybe he should have remembered to bring his steroids with him to Chicago—or at least the ones that cause a player to hit better with more home runs, and not the ones that cause a player to fly the bird while rounding the bases after hitting a HR.
But in the Steroid Era, baseball was run amuck with inflated numbers which the Cubs fell victim to on multiple occasions. It was a period of “nobody knew”, but “everybody knew.”
5. Free Agent Signing of Alfonso Soriano for 8 Years, $136 Million
When the Cubs offered Alfonso Soriano this contract, they had no idea it would become an albatross hanging around their neck, tightening year after year.
His 2006, contract-year season with Washington fooled the Cubs and other MLB clubs into rewarding Soriano with such huge contract offers to acquire his services. In 2006 he had a line of .277/.351/.560, with 46 HR, 95 RBI, and 41 SB, a fifth-in-a-row All-Star selection, and a Silver Slugger Award.
But like most clubs, the Cubs had a “what have you done for me lately” mentality and little regard for the long-term ramifications of a lengthy, high-priced contract when they considered the offer that landed them Soriano.
Soriano’s career numbers did make him a valuable free agent after the 2006 season, but an eight-year contract offer to a player who was 30 years old—after being 26 years old two years prior—and at $17 million per year, was a huge lapse in judgment.
Fonsi was a solid major leaguer during his pre-Cubs career, but more in the five-year, $13-15 million per year range.
The combination of the additional three years added to the contract, the extra $2-4 million and the no-trade clause all made this contract the worst in Cubs' history.
Soriano’s first two years with the Cubs were good—.291 BA, .888 OPS, 31 HR, 72 RBI, and 19 SB—but not worth the $34 million the Cubs paid him over that span. Still, there was little argument against his huge contract despite his missing 80 games between the two seasons.
Then came 2009.
In 2009, the injury bug continued to bite Soriano. That year his nagging injuries caught up to him and he fell off the proverbial table.
Soriano played in 117 games in 2009—up from 109 in 2008. His average fell from .280 in 2008 to .241 in 2009; his OPS fell .150 from .876 to .726; his RBI total dropped by 20, and his SB total was cut almost in half.
In 2010, his numbers saw an uptick nearly across the board from 2009 save the stolen bases department where the number again nearly halved due to age and nagging leg injuries.
Nevertheless, his performance still fell far below the value of his contract, and continued to do so in 2012 despite his notable improvement in overall play.
4. December 8, 1987: Lee Smith Traded to Boston
Why did the Cubs not see value in the closer role?
There was a span of roughly two seasons between 1984 and 1986 when the Cubs could have had a bullpen consisting of Bruce Sutter, Dennis Eckersley and Lee Smith. (Sutter retired in 1988 after missing the 1987 season with ATL.)
Lee Smith began his MLB career with the Cubs in 1980, and until his trading in 1987 he recorded 180 saves. He hit the 29 converted saves mark in 1983 and never earned less than that through 1996, except in 1989 with the Boston Red Sox when he recorded 25 saves.
Over his career, Lee Smith had a converted saves percentage of 82percent—fourth all-time behind Rivera, Hoffman, and Eck—out of 1289.1 innings pitched.
Many of Smith’s appearances were for more than one inning, unlike Rivera’s or Hoffman’s. He is considered to be a bridge between pitchers, who regularly threw multiple innings per appearance and had more wins and losses every season compared to the one-inning closers we have today.
Not only did the Cubs trade away three future Hall of Fame pitchers in the 1980s, but with Smith they traded away a significant piece of MLB history. And for that, it would have mattered little what Al Nipper and Calvin Schiraldi did in their brief time in Chicago; the Cubs would always come out the loser/moron/dunce/etc. in this trade.
3. Free Agent Signing of Milton Bradley to a 3-Year, $30 Million Deal
What really needs to be said about why this signing was one of the worst roster moves ever by the Cubs?
To say Milton Bradley had a long history of behavioral problems before signing with the Cubs would be accurate.
There was the speeding and attempted ticketing incident in Cuyahoga Falls, Ohio, in 2003 that earned him a three-day stint in jail. Then, in the closing week of the 2004 season, a fan threw a bottle at him and he returned the bottle to its origin whilst yelling at the crowd—receiving a season-ending suspension for his actions.
Or how about the time he tore his ACL arguing with a first base umpire about an alleged bat-throwing incident in a prior AB?
In 2008 he attempted to physically confront Kansas City Royals’ commentator Ryan Lefebvre in the press box post-game after Bradley believed Lefebvre’s comments to be of a derogatory nature in comparing him with Josh Hamilton.
But the one memory we all have of Milton Bradley is after he caught a one-out fly-ball at Wrigley Field during an interleague game against the Minnesota Twins, then proceeded to pose so “matter-of-factly” before throwing the ball into the right field bleachers.
After making negative and disrespectful comments about the Cubs organization, he was dealt to the Seattle Mariners for Carlos Silva on December 18, 2009.
1b. Letting Greg Maddux Leave Via Free Agency After Winning Cy Young
In his first stint with the Chicago Cubs, Greg Maddux earned one All-Star appearance, two Gold Glove awards, and the first of four consecutive National League Cy Young Awards.
He was arguably one of the greatest pitchers of all time—and the greatest of his era regardless of whether or not Roger Clemens used steroids. Letting Greg Maddux walk away was another example of the Cubs’ prominence in the pitching category of the “Blunder-ful World of Sports.”
Maddux’s Cy Young-winning 1992 season was the cap of a five-year period where he won 87 games in 176 starts, averaging 17 wins per season over those five years. In all, he won 95 games in his first stint with the Cubs.
But for whatever reason, the Cubs decided they had no need for a Cy Young winning pitcher just entering his prime. So after the 1992 season they allowed “Mad Dog” to leave and sign with the Atlanta Braves, where he won three more Cy Young awards, six All-Star selections, 10 consecutive Gold Glove awards, and 194 more games along with multiple World Series appearances and a World Series title.
Letting a player like Greg Maddux go with nothing to show for it would in most cases be any club’s—not just the Cubs’—worst player personnel move in their organization’s history. But for the Cubs, they have one more act of stupidity to rely upon as their trump card…against themselves.
1a. June 15, 1964: The Now-Infamous Lou Brock Trade
Originally, this list had the Lou Brock trade to the St. Louis Cardinals ranked as the second-worst roster decision made in Cubs history, behind the letting-go of Greg Maddux.
But both moves were equally devastating, hence the tie.
It’s not hard to believe the Cubs were thought to have gotten the better end of the trade when it was made.
Before trading Brock to the Cardinals he had only 22 SB—the stat he is most known for—and a .257 BA in two-and-one-third seasons with the Cubs, not counting the 1961 season where he appeared in only four games.
But then, like most players who were members of the Chicago Cubs before finding their way to St. Louis, he showed how much the Cubs erred in not keeping him.
From 1969 to 1974, Lou Brock recorded consecutive seasons of 190+ hits. From 1965 through 1976, he recorded 12 consecutive seasons of 50+ stolen bases. He set a then-record of 118 SB in 1974, eclipsed only by Rickey Henderson’s 130 in 1982.
He won World Series titles in 1964 and 1967 with the St. Louis Cardinals, winning the Babe Ruth Award for his performance in the 1967 World Series.
What makes this trade so, so bad for the Cubs is not so much that he went on to become the player he did. If the Cubs had kept him and put him alongside Ernie Banks, Ron Santo, Billy Williams and Fergie Jenkins, there would never have been any talk about 1908 nor any attention paid to a black cat crossing in front of Ron Santo in the on-deck circle.
That is why this trade is so horrendous: the “What Could Have Been.” Cubs’ fans would never have had to suffer through generations of misery.
Lou Brock was our Babe Ruth; it is that simple.
The Cubs trade that sent Bruce Sutter to the Cardinals on December 9, 1980, almost made the list, but the returns they received via Leon Durham from 1981 to 1987 mitigated the consequences.
Also, it would have been redundant to have this trade, the Eck trade, and the Lee Smith trade all on this list.
But the Sutter trade was nonetheless a bonehead decision.