Sports fans always want to think they could run their favorite team better than whoever is currently doing it, and the decisions on this list are the reasons why. Despite the amount of money and time invested in scouting, player development and organizational management, franchises continually make drastic mistakes that set back their team for years. The recent trend for teams such as the Philadelphia 76ers and Buffalo Sabres to “tank” for a better draft pick has called to question what is the best way to build a contending team. While some teams have consistently seen free agency as an opportunity to quickly construct the perfect team, others opt for slowly building through acquiring young talent.
The teams on this list often made the mistake of prioritizing the present while sacrificing their future. Teams that are consistently successful tend to do use all avenues to build their team, drafting, player development, free agency and building a winning culture. There is no one right way to build a winner and how a team decides to do so is usually dependent on ownership. Many of the decisions in this list may have made sense at the time, only to look increasingly worse as time passed. There a number of decisions on this list however that were mistakes the moment they were made. These poor decisions were often made for two reasons, overlooking the future to benefit the present and ignoring important factors in the decision. This list will show how despite the collective “expertise” within sports teams, mistakes are still made more often than they probably should.
20. The Charlotte “Bobcats”
The Charlotte Hornets were one of the more beloved teams in the 1990’s but diminishing attendance led the NBA to approve their relocation to New Orleans in 2002, and along with them went the Hornets team name. When the NBA decided it would award Charlotte an expansion franchise in the 2004 season, the hope was that the Hornets name could return to its rightful home. New Orleans however remained the Hornets and Charlotte settled on its new name, the Bobcats. The Bobcats were perennially terrible posting some of the worst records in league history and continually failing to draft a star player. The time the franchise spent as the Bobcats was one of the worst stretches in NBA history.
When New Orleans decided to change their name to the Pelicans in 2013, the opportunity arose for Charlotte to reclaim the Hornets. Charlotte has rightfully returned to its roots as the Hornets, putting in a new floor with a honeycomb pattern and affectionately calling their arena “the hive” as their franchise seeks to regain the credibility it lost as the Bobcats.
19. Ditka trades his whole draft for Ricky Williams
The history of trading away multiple picks to move up a few slots in the draft does not usually bode well for that team. In 1999 Saints head coach Mike Ditka saw stud running back Ricky Williams coming out of Texas as a workhorse back that could be a star in the league for years. Ditka traded every pick they had that year, along with their first and third round picks the following year, to the Redskins to move up to the 5th pick and select Ricky Williams.
Williams played in only three seasons for the Saints before being traded to the Miami Dolphins where he would become the leading rusher in the NFL. Williams failed to lead the Saints to the playoffs during his brief time there and the loss of draft picks set their team back for years. Williams would go on to have a tumultuous career after testing positive for marijuana and taking time off from football.
Amazingly, the Washington Redskins also failed, as they were unable to turn those picks into a Super Bowl team.
18. Nets/Knicks: Selling Dr. J / Passing on Dr. J
Its scary to think what a player of Dr. J’s stature would get in an open market today. Julius “Dr. J” Erving was a legend in the ABA that changed the game with his athleticism. When the Nets joined the NBA they were forced to pay the Knicks a fee for coming into their market, which forced the Nets to come up with money to appease the Knicks. Unable to come up with the money, the Nets’ owner decided to leverage his best asset, “Dr. J”. He offered the Knicks Dr. J as a means to cover the cost, but the Knicks refused so the Nets sold Dr. J’s rights for $3 million the Philadelphia 76ers. Dr. J would go to make 11 NBA all-star games and win the title in 1983.
17. Letting Jim Harbaugh Walk
We’re going to go ahead and already call this one a mistake. Jim Harbaugh was hired as head coach in San Francisco in 2011 and took a team that had been struggling for years back into the league’s elite. With Harbaugh as their coach the 49ers won back-to-back division titles and made the Super Bowl in 2012. Harbaugh made the difficult choice to bench proven starter Alex Smith for unproven talent Colin Kaepernick, a move criticized by many that helped propel their team into Super Bowl contention.
After the 2013 season and despite a 12-4 winning record, rumors started that regardless of the upcoming season, Jim Harbaugh would not be returning to the 49ers because of differences with ownership. After the 2014 season Jim Harbaugh and the 49ers mutually parted ways (Harbaugh says he was let go). Harbaugh was a top-5 coach in the NFL during his time and was let go for no reason other than ownership finding him difficult. This decision will likely haunt the 49ers for years as they try to find his replacement.
The 49ers offseason has simply been abysmal and it all started with letting Harbaugh walk off to Michigan.
16. Wayne Gretzky Trade
Few athletes mean more to a city than the great one did in Edmonton. Considered the greatest player of all time, Gretzky led the Oilers to four Stanley Cup championships and was an icon of the city. The sports world was shocked when mere weeks after winning leading the Oilers to a sweep in the Stanley Cup finals, The Oilers traded Gretzky to the L.A. Kings for three first round picks and $15 million in cash (along with other players involved in “The Trade”.
The trade was considered inevitable by management as Gretzky wanted to go to L.A. and they had little chance of re-signing him when he became a free agent. The fans however did not agree with that logic and are still hurt by the decision.
The Oilers would continue to succeed for a couple more years, winning the cup in 1990 but fans still haven’t forgiven the decision. It’s difficult to fault the Oilers but some players are not tradeable, regardless of the offer. The trade also began an exodus of talent from the team as other stalwarts such as Mark Messier and Jari Kurri would also leave the team a couple of years later.
15. Timberwolves Talking to Joe Smith
Joe Smith was the first overall pick in the 1995 NBA Draft by the Golden State Warriors. Smith started his career strong but was traded to Philadelphia in 1998. Smith became a free agent in that summer and had many suitors trying to lure the former top talent. Despite the multitude of interested teams, Smith signed a curious contract with the Wolves, opting for less money.
The NBA has rules protecting against teams making promises to players regarding their future contracts and a few years into his time with the Wolves, the NBA became aware that Smith had agreed to sign with the Wolves because Wolves GM Kevin McHale had promised a his next contract would be very lucrative.
For this violation of the salary cap the Wolves were stripped of five first round picks (although they would only end up losing three) which set their franchise back and made it difficult to build their team around their budding superstar Kevin Garnett.
14. Oakland drafts JaMarcus Russell 1st Overall
The Oakland Raiders have made a number of questionable decisions in recent years but none has set them back as much as drafting JaMarcus Russell first overall in 2007. Russell was coming off a steller season in college but it was his combine and workout performances that vaulted him to the top of the draft. Russell was the type of prospect front offices drool over. He was massive for QB standards and could throw the football 70 yards.
Unfortunately for Russell and the Raiders, there is more to football than arm strength and bench presses. Russell struggled with accuracy and his work ethic was continually under question as he would report to training camp overweight and under prepared. Russell was released before the 2010 season and has never played again in the NFL. Players that the Raiders passed on include All-Pros Calvin Johnson, Joe Thomas and Adrian Peterson.
13. Dodgers Trade Pedro Martinez to Montreal
In 1993, Pedro Martinez was traded from the L.A. Dodgers to the Montreal Expos for second-basemen Delino DeShields. Pedro would go on to establish himself as one of the best pitchers of all time while DeShields played three mediocre seasons for the Dodgers. Pedro would win his first Cy Young with the Expos in 1997, posting a 1.90 ERA. The Expos would end up trading Pedro to Boston, as they couldn’t afford him with Martinez approaching free agency.
It would make some sense if the Dodgers traded Pedro before he had established his talent, but he posted a 10-5 record and averaged over a strikeout per inning the season he was traded. The trade did not seem egregious at the time as DeShields was coming off a few good seasons to start his career, including hitting .294 with 45 stolen bases the season before he was traded.
12. The James Harden Trade
What looked bad at the time has quickly become a disaster. The Thunder were poised to become perennial championship contenders with a young nucleus that had three MVP caliber players (Harden, Westbrook, Durant) and one of the best defensive big men in the game (Ibaka). The Thunder spun the story that they couldn’t afford to pay both Harden and Ibaka, which was not really the case. Reports were that the Thunder and Harden were only about $1 million a year apart in their negotiations for an extension but the Thunder were not budging and traded Harden to the Rockets for Jeremy Lamb, Kevin Martin and a first round pick that would become Steven Adams.
While Adams looks like a solid pro, Martin is no longer with the team and Lamb rarely plays. Harden however has become a MVP contender leading one of the best teams in the Western Conference. With Durant’s injuries and the impending free agency of he and Westbrook, it is difficult to think that the Thunder had that core of players and may never get a championship out of it. With Durant set for free agency in 2016, their window is quickly closing, if it hasn’t already.
11. Redskins Go All In For Robert Griffin
Robert Griffin was viewed as a can’t-miss prospect in the 2012 NFL Draft coming off his Heisman Trophy season in Baylor. The Rams had the 2nd pick but had recently drafted QB Sam Bradford first overall and weren’t ready to move on yet so they sought to trade their pick to the highest bidder and to no surprise that was the Redskins. The Rams received three first picks and one second round pick in the trade. Griffin started his career off as the best offensive rookie in the league but his slight build and tendency to take off and run has led to a series of serious knee injuries.
As Griffin has tried to become more of a pocket passer his fundamental shortcomings have become increasingly evident and this past season he spent time as the backup watching Kirk Cousins, and even Colt McCoy. The Rams have not necessarily used those picks in the best way possible but they found productive starters for their young defense including Michael Brockers and Janoris Jenkins.
10. Letting LeBron Down
LeBron was the best player in the league and was a generational talent playing for his hometown team but Cavs management decisions made his choice to go to Miami inevitable. Players of LeBron’s stature are always judged by championships and if he felt that he could have won one in Cleveland, he would have stayed there. General manager Jim Paxon could not find the right talent to surround LeBron during his first seven years in the league and it cost him his job.
The best teammates LeBron had in Cleveland included Mo Williams, Larry Hughes, and an aging Shaq. Paxon’s failure to secure an agreement to resign Carlos Boozer when Boozer decided to change his mind and sign with Utah was a massive blunder on his part. Players of LeBron’s level are rare and franchises need to do everything they can to put a team around them and not assume they will always be there.
9. Jaguars Fire Tom Coughlin
Longtime Jaguar Tony Boselli said of the Jags firing Tom Coughlin, “”One of my regrets for the franchise is I think he could’ve been a Tom Landry, Chuck Noll type of guy in Jacksonville and stayed there forever,” Boselli said, per the New York Daily News. “You talk to people in Jacksonville now, since he left he’s still one of the most popular people in town. And I think for the longest time, people were like, ‘Man, why did we fire Tom?’ ”
Former Jacksonville Jaguars owner Wayne Weaver said it himself, that firing Coughlin was his biggest regret.
In Coughlin’s tenure with the expansion franchise, he led them to two AFC Championship Games, a 68-60 record and a 4-4 playoff record. The team struggled in Coughlin’s final three years, but the franchise’s futility following his 2002 departure and his two Super Bowls in New York make this mistake stand out.
8. Mike Milbury’s tenure with the Islanders
Sometimes the worst decision a franchise makes is who they put in place to make all the decisions. Mike Milbury’s tenure with the New York Islanders saw some of the most baffling decisions in sports. Milbury was not aided by ownership that had given him the mandate to maintain a laughably low team salary. As a result the team lost star scorer Zigmund Palffy for practically nothing.
With that granted, it doesn’t excuse Milbury for trading top tier talent so early in their career, when they were still cheap, including Zdeno Chara, Wade Redden, Roberto Luongo and Todd Bertuzzi. Milbury also made the confusing decision to take goaltender Rick DiPietro first overall ahead of top prospects like Dany Heatley, especially when the team had just drafted Luongo a couple of years prior. Milbury also doubled down on his poor decision when he signed Rick DiPietro to a stunning 15-year contract. For the coup de gras, Milbury traded for Alexei Yashin, which sent Chara, Bill Muckhalt and their second overall pick in 2001 to Ottawa. That pick turned out to be Jason Spezza.
These decisions set the Islanders back for years which hurt their attendance, fanbase and stature in the league. It’s very plausible that if Milbury had simply held on to these young pieces, the Islanders could have added a couple of Stanley Cups to their repertoire.
7. Oden over Durant
Teams like the Knicks and Lakers picking near the top of this year’s draft need to pay attention; taller is not always better. The notion that “you cannot pass up size” has existed for too long in the NBA. Teams that tend to dominate in the current NBA are led by guards and wings and the value of a post-up big man is diminishing quickly. In 2007, Lamar Oden was a can’t-miss prospect, someone who could protect the rim for your team for the next decade.
It’s easy to call this bad luck for the Blazers as Oden’s injuries robbed him of his career, except that he had those injury concerns before being drafted. The history of injury-prone big men is not bright and teams made too much of Durant’s slight build (his combine bench press is the stuff of legend). Durant has gone on to become the 2nd best player in the league, winning the MVP last season and making the Thunder one of the best teams in the league.
6. Lions give Matt Millen the keys
There are few general managers in sports history that can claim to be as hated as Millen was towards the end of his tenure with the Lions. The “Fire Millen” movement in Detroit was as passionate their fanbase had been in years. Millen was hired out of broadcasting and had no previous experience running a team when he took over the Lions in 2001. Millen oversaw one of the worst teams in all of sports during his time with the Lions as they went 31-84 under his direction. Millen had a confusing affinity for taking receivers in the first round, drafting busts Charles Rogers, Mike Williams and Roy Williams within four years, before finally landing Calvin Johnson in his last year in control. The Lions are only now recovering from these dark years with a team that has Calvin Johnson as the only remaining Lion that played during Millen’s tenure.
5. Drafting Darko
The 2003 NBA draft was one the best of all time and among the future hall of famers, were the Detroit Pistons picking 2nd and selecting Darko Miličić. This draft was near the height of the NBA’s infatuation with European prospects, especially tall skilled players, as every team was searching for the next Dirk Nowitzki. The Pistons were coming off the Eastern Conference Finals and had the rare high pick for a contending team.
The Pistons passed on Carmelo Anthony, Chris Bosh, and Dwyane Wade to take Darko. Perhaps a bigger mistake than drafting Darko was the lack of playing time he was given. On a veteran contending team, Darko struggled to get on the court and was eventually traded to the Magic for a first round pick. Darko bounced around the league before officially retiring in 2014 to pursue a kickboxing career. The Pistons have struggled mightily since the Billups-Ben Wallace days and could have bridged to a new generation had they used their pick wisely.
4. Knicks hire Isiah Thomas
Great players often think they know the game so well that they can coach and even run franchises, but it’s not as easy as it looks. The Knicks brought in Isiah to run the team and he quickly started what has become the worst era in Knicks history. Thomas made a number of mistakes during his tenure including signing Jerome James for $30 million and trading for Eddy Curry and Steve Francis. The Knicks’ salary cap numbers were enormous during his tenure, despite their lack of success. Thomas has been shunned from any further NBA team positions since his time with Knicks and that isn’t going to change anytime soon.
3. Kobe Bryant Trade
It’s difficult to imagine an NBA without Kobe as a Laker. The Lakers traded centre Vlade Divac for Kobe Bryant, who had just been selected 13th overall by the Charlotte Hornets. Vlade would go on to have a solid career but Kobe is the defining player of his generation. In the rich history of the Lakers, Kobe is possibly the definitive Laker, winning five rings over his career and setting scoring records, including his 81-point game. At the time he was only a 17-year old out of high school that was selected 13th but in hindsight, it is one of the most lopsided trades in sports history.
2. Herschel Walker Trade
Given the diminishing value of running backs in today’s NFL the Vikings-Cowboys trade involving Herschel Walker seems even more baffling. In 1989, the Cowboys traded star running back Herschel Walker to the Vikings in the most lopsided trade in history. The Cowboys were a cellar dweller in the league and saw trading Walker as a means to build their team. In return for Walker the Cowboys received three first round picks and three second round picks, among other assets.
The Cowboys used those picks to draft cornerstone pieces including Emmitt Smith, Russell Maryland, Kevin Smith, Darren Woods, who would all help the Cowboys become the team of the 90’s, winning three Super Bowls. While the Cowboys were beginning their dynasty, Herschel Walker would disappoint in Minnesota, being released in 1992.
1. Babe Ruth for a Musical
Red Sox owner Harry Frazee needed cash to finance the musical “No, No, Nanette” so he decided to sell the best player in baseball to their rival New York Yankees for $100,000 and a $300,000 loan and the ‘Curse of the Bambino’ was born. The Babe would go on to win four World Series with the Yankees and hit 714 home runs as one the most iconic athletes of all time and possibly the greatest Yankee ever. The Red Sox World Series drought would last 86 years, winning three in the last decade (2004, 2007 and 2013). When a move like this affects your franchise for nearly a century, and strengthens your rival, it’s easily the biggest franchise mistake in the history of sports.
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