Cursed Cubs: 7 Bad Trades, 7 Bad Signings And 7 Bad Draft Picks

When it comes to hexes in the world of sports, few are as infamous as the “Curse of the Billy Goat.”

As legend has it, the curse began back in 1945, when a bar owner by the name of William Sianis was asked to leave, due to the unpleasant odor associated with his pet goat. Before exiting Game 4 of the World Series that year, Sianis famously declared, “Them Cubs, they ain’t gonna win no more.”

The Cubs would go on to be defeated by the Tigers in the 1945 World Series and wouldn’t win another world championship until 2016 – roughly 71 years later. In truth, even prior to the curse, it had been a while since the Cubbies had won it all – as their last world title win came back in 1908. In fact, by the time the final out was made in the 2016 World Series, it has been roughly 108 years since the Chicago Cubs were crowned champions.

However, when one takes a closer look at the Cubs' drought, it may have been more than a smelly goat that caused the historic franchise to struggle for so many years. In truth, a series of poor managerial decisions likely had far more to do with the team’s world title drought, then the words of a disgruntled bar owner.

With that in mind, it’s time to take a look at some of the worst moves in Chicago Cubs history during the “cursed” years. These awful signings, draft choices, and trades will still make any Cubs fan cringe.

21 Trade: Lou Brock For Ernie Broglio

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Brock for Broglio is easily the most famous trade in Chicago Cubs history and is also among the worst. The 1964 exchange between the Cubs and Cardinals involved a total of six players with Lou Brock and a pitcher named Ernie Broglio being the centerpieces. While the Cubs liked Brock’s speed, they were unimpressed with his batting average (.260) at the time, so they sent him to St. Louis for Broglio – who had led the National League in wins for four consecutive years.

Brock would finish his career with a .293 batting average and go on to become the all-time stolen base leader. The six-time All-Star and Hall of Famer was also a member of two World Championship teams in St. Louis. Conversely, Broglio’s arm was shot by the time he put on a Cubs uniform, and after less than two seasons, he was sent down to the minors.

20 Signing: Milton Bradley

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Outfielder Milton Bradley was an outstanding hitter for a good portion of his career. Unfortunately, he also had a reputation for being a hothead and had some personal issues off the field as well. However, these issues didn’t stop the Cubs from signing him to a three-year, $30 million deal in 2009.

At the time, the Cubs were managed by Lou Piniella – who was known as something of a hothead in his own right. Bradley got off to a rough start in Chicago and was suspended for making physical contact with an umpire. Predictably, Bradley also had a verbal altercation with Piniella, after assaulting a Gatorade cooler. The outfielder hit just .257 in his only season as a Cub, before being shipped off to Seattle.

19 Draft: Bob Welch

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In most cases, drafts busts tend to be early picks who don’t pan out. However, in this instance, the Cubs made an excellent choice but failed to sign them. Moreover, they passed on a chance to draft a top RHP when a second opportunity arose.

The Cubs originally drafted Bob Welch in the 14th round in 1974, but the pitcher opted to go college instead of sign a pro deal – this sort of thing happens fairly frequently. However, the Cubs had a chance to draft him again in 1977 but went with a pitcher named Randy Martz instead. While Martz never amounted to much, Welch would go on to win the Cy Young Award in 1990 and was also a member of three World Series winning teams.

18 Trade: Rafael Palmeiro

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It isn’t clear why the Cubs decided to part way with first baseman Rafael Palmeiro. Some believe that the team’s management simply preferred Mark Grace at first, though there were also rumors that he had some off-field issues with Cubs star Ryne Sandberg. Whatever the case, Chicago traded Rafael Palmeiro, Jamie Moyer, and Drew Hall to the Rangers for six players – with the most noteworthy being pitcher Mitch Williams.

Palmeiro went on to have Hall of Fame worthy career as .288 hitter with 569 home runs. However, his off-field issues make it unlikely that he’ll ever be enshrined in Cooperstown. Williams had one good season as a reviler for the Cubs, but that’s about all they got out of the deal.

17 Signing: Todd Hundley

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As a member of the New York Mets in the mid-90s, Catcher Todd Hundley established himself as one of the game’s premier power hitter. In fact, in 1996, he broke the single-season home run record for a catcher, by hitting 41 long balls that season. When Hundley became available in 2001, the Cubs signed him to four-year, $23.5 million contracts.

Unfortunately, for the Cubbies, Hundley had a tough time in Chicago. During his two seasons with the team, he batted .199 and hit a total of 28 homers. He wasn’t exactly a fan favorite either and was frequently booed by Cubs fans for not living up to their expectations.

16 Draft: Bobby Brownlie

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In the 2002 draft, the Cubs selected a right-handed pitcher by the name of Bobby Brownlie with the 21st overall pick. At one point, the righty out of Rutgers was considered to be good enough to warrant the No. 1 overall pick. However, his velocity had dropped off, and he was having arm trouble prior to the draft.

The Cubs decided to take a chance with their first pick, but it didn’t pay off. Brownlie would never even make to the Majors. A few picks later the San Francisco Giants would draft a pitcher out of Houston High School by the name of Matt Cain.

15 Trade: Nomar Garciaparra

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In 2004, the Cubs hoped that acquiring infielder Nomar Garciaparra would be enough to secure a spot in the playoffs. Garciaparra was acquired in a f0ur-way trade that involved the Red Sox, Twins, and Expos. The Cubs didn’t give away any key players to acquire the star infielder, but they did sign him to a one-year contract extension worth $8.25 million as part of the deal.

Garciaparra batted .297 during the Cubs reaming 43 games that season, but the team still missed the playoffs. The following year, in 2005, he batted .283, which was solid. However, he struggled in the power department – managing to hit just 9 homers during his second season in Chicago. The team decided not to re-sign him in 2005.

14 Signing: Alfonso Soriano

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As part of the Cubs infamous 2006 spending spree, the team signed middle infielder Alfonso Soriano to an eight-year deal, worth an eye-popping $136 million. This was the richest long-term deal in team history at the time. Soriano wasn’t a total bust, but he wasn’t worth anywhere near the price the Cubs paid for him.

In 2007, his first season as a Cub, Soriano suffered a torn quad. As a result of the injury, Soriano was never the base stealing threat he was in his prime. His defensive skills and batting average also began to decline in Chicago. On the plus side, he did hit a lot of homers in a Cubs uniform, but that was about it.

13 Draft: Lou Montanez

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In the 2000 MLB draft, the Chicago Cubs selected shortstop Lou Montanez with the third overall pick. Billed as the second coming of Alex Rodriguez, Montanez was an offensive middle infielder with a great deal of hype surrounding him.

Montanez never came close to living up to expectations. He spent seven seasons in the Cubs minor league organization and was eventually released in 2007. He signed another minor league deal with the Orioles and eventually made his MLB debut in August of 2008 – though he didn’t have much success in Baltimore either. Over the course of his entire Major League career, Montanez hit just .223 with a grand total of 5 home runs, and 32 runs batted in.

12 Trade: Lee Smith

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Pitcher Lee Smith is widely considered one of the top relievers of his era – who many believe should be in the Hall of Fame. Lee had led the league in saves in 1983 and was coming off of his second All-Star appearance in 1987 when the Cubs decided to trade him for the pitching duo of Al Nipper and Calvin Schiraldi.

Following the trade, Al Nipper ended up pitching just 104 more innings at the big league level. Schiraldi struggled for two seasons in Chicago, before being traded to the Padres. Conversely, Lee Smith would go on to record 300 more saves. If not for the Lou Brock deal, this would probably be remembered as the worst trade in franchise history.

11 Signing: Danny Jackson

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Danny Jackson had been a part of two World Series Championship teams with the Royals and Reds respectively. He had also had a 23-win season in Cincinnati – making him a highly sought-after free agent in 1990. In the end, after offering him $2.6 million a season (which was a lot at the time) for his services, the Cubs ended up signing Jackson.

However, Chicago didn’t get their money's worth out of the lefty. In 1991, his first season with the team, he went 1-5 with a 6.79 ERA – before landing on the DL. The next year he posted a 4.22 ERA with a 4-9 record, before ultimately being traded to the Pirates.

10 Draft: Brooks Kieschnick

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With the 10th overall pick in the 1993 amateur draft, the Chicago Cubs selected an outfielder named Brooks Kieschnick. GM Larry Himes, who was brought over from the White Sox, felt he compared favorably to Hall of Famer Frank Thomas. However, Brooks Kieschnick has no Frank Thomas – not even close.

The outfielder played only a handful of games for the Cubs and spent the majority of his career in the minors. He re-emerged as a Brewer in 2004, where he played for two seasons, before being sent down to the minors and ultimately retiring. Some of the players the Cubs passed on to draft Kieschnick include Derek Lee, Chris Carpenter, and Torii Hunter.

9 Trade: Dennis Eckersley

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Dennis Eckersley was an outstanding starter pitcher during the early portion of his career and even made a couple of appearances in the All-Star Game. However, as a member of Cubs in the mid-'80s, the right-hander was struggling with alcoholism, which caused his performance on the field to deteriorate. As a result, in 1987, Chicago traded Eckersley and a guy named Don Rohn to Oakland for the trio of Dave Wilder, Brian Guinn, and Mark Leonette.

Eckersley revitalized his career in Oakland by becoming one of the greatest closers of all time. He went on to win the Cy Young Award in 1992 and was inducted into the Hall of Fame in 2004. On the other hand, if not for the trade itself, no would even remember the names Wilder, Guinn, and Leonette.

8 Signing: Kosuke Fukudome

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In December of 2007, the Cubs signed Japanese outfielder Kosuke Fukudome to a four-year, $48 million contract. Due to his speed, defensive skills, and hitting prowess, Fukudome was poised to be the latest breakout star from the Japanese leagues. However, he turned out to be little more than a serviceable MLB starter.

Despite all the hype surrounding him, Fukodome’s best season on the Cubs was 2010, when he posted a .262 batting average and hit 13 home runs. In 2011, the team decided to trade him to the Indians for a couple of minor league prospects. While his play never came close to warranting the contract he received, he did have one of the league’s best-selling jerseys during his stint in Chicago.

7 Draft: Earl Cunningham

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In 1989, the Cubs were thrilled to land an outfielder by the name of Earl Cunningham with the 10th pick of the draft. With his impressive power and magnificent speed, Cubs management believed Cunningham had star potential.

The young outfielder was indeed strong and fast. Unfortunately, he never learned how to hit a curveball. As a result, the 10th overall pick never made out of the minors. On the plus side, the best player from the draft, Frank Thomas, was selected just before Cunningham, so at least the Cubs don’t have to say they passed on one of the all-time greats to draft a player that no one remembers.

6 Trade: Bill Madlock

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Bill Madlock was a third baseman who won two National League batting titles as a member of the Chicago Cubs in 1975 and 76. However, Madlock made contract demands that Cubs management wasn’t willing to accommodate. Instead of paying the star third baseman, they traded him and Rob Sperring to the Giants for a minor league pitcher named Andrew Muhlstock, Steve Ontiveros and Bobby Murcer.

Madlock would go on to capture two more batting titles. He was also a member of the Giants team that won the World Series in 1979. On the other hand, Murcer hit 27 homers, his first year in Chicago but didn’t do much after that. Muhlstock never made to the majors and Ontiveros had a mostly forgettable run with the Cubs.

5 Signing: Candy Maldonado

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Following the 1992 season, the Cubs decided not to renew outfielder (and now Hall of Famer) Andre Dawson’s contract. The franchise believed they could get similar production from Candy Maldonado, who had a nice postseason with Blue Jays the previous year. Chicago gave him a $1.65 million contract – which was a decent chunk of change in the early '90s.

As Cubs nation soon discovered, Maldonado was no Andre Dawson. In his first (and only) season as a Cub, the former Blue Jay finished the year with a .186 batting average and hit just 3 home runs. That same year (1993), an aging Andre Dawson hit .277 with 13 home runs.

4 Draft: Ty Griffin

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Back in 1988, the Cubbies decided to spend their first-round pick (ninth overall) on a second baseman named Ty Griffin. Prior to joining the Cubs minor league organization, Griffin had won an Olympic gold medal as part of the United States national baseball team. As it turned out, capturing the medal would be, by far, his biggest accomplishment in the sport.

Sadly, the second baseman would join the list of Cubs prospects that never made it out of the minors. With the very next pick in the 1988 MLB Draft, the White Sox selected Robin Ventura, who made two All-Star appearances and won six Gold Glove Awards.

3 Trade: Bruce Sutter

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Bruce Sutter is a Hall of Fame pitcher who finished his career with a 2.83 ERA and 300 saves. During his time as a Chicago Cub (1976-1980), he made multiple All-Star appearances and even captured the National League Cy Young Award in 1979. Following the 1980 season, an arbitrator awarded Sutter a $700,000 contract, which the Cubs had no interest in paying. As a result, he was traded the Cardinals for Leo Durham, Ken Reitz, and a player to be named later.

Reitz didn’t pan out. However, Durham had some solid seasons as a Cub. Still, the Cardinals received a Hall of Fame closer and clearly got the better end of the deal.

2 Signing: Dave Smith

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In 1991, the Cubs signed pitcher Dave Smith to be their new closer. Prior to coming to Chicago, Smith played with the Houston Astros where he had established himself as a reliable closer. The Cubs signed Smith to a two-year deal for $4.9 million. At the time, he was making more money than established stars like Ryne Sandberg.

Unfortunately, Smith’s tenure as a Cub was a disaster. He finished his first season with the team sporting an underwhelming 6.00 ERA. During his second season in Chicago, 1992, Smith dealt with several injuries that ended his playing career; he appeared in just 11 games that year.

1 Draft: Drew Hall

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With the third overall pick of the 1984 MLB Draft, Chicago decided to go with a left-handed pitcher out of Louisville, Kentucky named Drew Hall. Unlike many of the draft picks on our list, Hall actually made it to the pros – though he had little success at the big league level.

In three seasons with the Cubs, he managed to win only three games and finished his final season as a Cub (1988) with a 7.66 ERA. However, he still has the distinction of being the highest MLB draft pick out of the state of Kentucky. Unfortunately, he was probably best remembered for being part of the trade that sent Rafael Palmeiro to the Rangers.

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