The 25 Dumbest Front Office Moves in Sports History

Image via Complex Original

It ain't easy running a sports franchise. While you can make a few decisions that receive praise by the media, it only takes one regrettable choice to make you remembered as one of the worst owners or GMs in sports history. There's always the one that got away. That one beauty who you wished they held onto, only to see them doing well on someone else's team. Wait, are we still talking about sports? Sorry, got a little sidetracked.

Anyway, in light of these mistakes we present you with a list of worst decisions ever made by the people running the show. From Isiah Thomas giving Eddy Curry $60 million to ride the bench to the Red Sox trading away Babe Ruth to the Yankees in exchange for an 86-year championship drought, here are The 25 Dumbest Front Office Moves in Sports History.

25. McDaniels vs. Cutler

Dumbass Move By: Josh McDaniels and the Broncos Front Office
Date: 2009

A couple years before Tim Tebow came to town and started miraculously winning games for the Broncos there was the Jay Cutler trade fiasco. In something straight out of a soap opera, word got out that head coach Josh McDaniels (former Pats offensive coordinator) was in trade talks with New England to acquire Matt Cassell for Cutler in a three-team deal. Well, that didn't work out and Cutler's feelings were hurt (SMH, some QBs are softer than kickers). After a conference call between McDaniels, Cutler, and the Broncos front office patch things up so Cutler sold his home and requested a trade. The Broncos fulfilled his request sending Cutler and a fifth-round pick to the Bears in exchange for Kyle Orton along with two first and one third-round picks. The Broncos used one of those picks on Tebow and Orton was released from the team last week after spending months on the bench. We're pretty sure the Broncos fans will have a more detailed account in the New Testament.

24. Yankees Sign Carl Pavano

Dumbass Move By: Brian Cashman and the New York Yankees
Date: 12/20/2004
The Yankees don't come close to their crosstown rivals when it comes to bad front office decisions. But being a New York sports team they do have a rep of splurging on players who aren't really worth it. One of the biggest examples of this came when the Yanks gave Carl Pavano a four-year deal worth $39.95 million. In return, Pavano pitched in a grand total of 26 games...in three years. Plus, he never had an ERA under 4.76. Everything from broken ribs to an injured buttocks kept Pavano out of the Yanks rotation during his tenure. Yup, you can say this investment was a pain in the ass.

23. Michael Jordan Drafts Kwame Brown

Dumbass Move By: Michael Jordan
Date: 6/27/2001
Michael Jordan is widely regarded as the best to ever play in the NBA. But when it comes to making basketball decisions, MJ is the furthest thing from the best in basketball. During the 2001 NBA Draft, Jordan used his first overall pick to take a chance on high school prospect Kwame Brown and that decision didn't pan one bit. Brown spent the majority of his time on the bench, battling injuries, or just plane sucking. After a few stints with other teams and nearly a decade later Kwame signed a deal with the Bobcats who are owned by, you guessed it, MJ! Reunited and it feels so...terrible?

22. Chelsea Doesn't Get Their Money's Worth For Shevchenko

Dumbass Move By: Roman Abramovich and Chelsea
Date: Summer 2006
A favorite player of Chelsea owner Roman Abramovich, Andriy Shevchenko was transferred from A.C. Milan for €44 million, or $58.66 million. In only 48 games (and three years) with Chelsea, Shevchenko scored a meager nine goals. And it wasn't that he turned into a bust because later on in his career with FC Dynamo Kyiv, he scored 21 goals in almost the same number of appearances. Failing to rise to the occasion? Think they got a pill for that. Pause.

21. Redskins Nine-Figure Deal To Albert Haynesworth  

Dumbass Move By: Daniel Snyder and the Washington Redskins
Date: 2/27/2009
The contract year performance. All GMs fall victim to the allure of an athlete that puts up great numbers the season before their current deal comes to an end. But no one falls for it quite like Redskins' decision maker, Daniel Snyder. In an effort to trump all his other idiotic choices in the past, Snyder rewarded defensive tackle Albert Haynesworth with a 7-year, $100 million contract after he recorded a career-high 8 1/2 sacks during the 2008 season. After two unproductive years in Washington where Haynesworth had only 6 1/2 sacks, the 'Skins ended up releasing him and shelling out nearly $36 million to get him off the team. When a team would rather throw away that much money than see your mug in the locker room again, that should tell ya something.

20. Canadiens Trade Patrick Roy

Dumbass Move By: Ronald Corey and the Montreal Canadiens
Date: 12/6/1995
When it was said and done, Patrick Roy ended up becoming one of the best goalies to ever play the game. But could you imagine that the Canadiens traded him because of one bad game? In a match against the Red Wings on December 2, 1995, Roy didn't have his best stuff on the ice and gave up five goals in the first period. After getting denied a request to get pulled from the game, St. Patrick gave up another four goals and was finally pulled in the second period. Upon leaving the rink, Roy told the owner that "It's my last game in Montreal." Ronald Corey obliged and Montreal hasn't won another chip since then. The Curse of Roy is alive and well.

19. "The Stepien Rule"

Dumbass Move By: Ted Stepien
Date: 1980-1983
When you have a bone-headed rule actually named after you, it's not a good sign for any general manager. Cleveland Cavaliers GM Ted Stepien became infamous for trading away his team's first-round pick in consecutive years for mediocre talent which is why the team went 66-180 during his tenure. As a result "The Stepien Rule" was enacted, preventing teams from trading first-round picks for consecutive years. The lowlight of Stepien's tenure came when he traded first round picks and as a result passed on a chance at getting James Worthy. See, Cavs fan were taking major Ls way before Bron Bron dipped out.

18. Mets Trade Top Pitching Prospect For Crumbs

Dumbass Move By: Jim Duquette and the New York Mets
Date: 7/30/2004
If you're going to trade away your top pitching prospect, you should get something valuable in return. At least that's what we believe. Apparently, former Mets GM Jim Duquette doesn't go by that same mentality, which is the only plausible explanation for giving away their best pitcher in the farm system Scott Kazmir for Victor Zambrano. FYI: During the previous season, Zambrano led the AL in walks, hit batsmen and wild pitches. Is it any mystery why Duquette hasn't had another general manager job since then? This was just another one of the many Mets fails over the years.

17. The T'Wolves Trade Garnett

Dumbass Move By: Kevin McHale and the Minnesota Timberwolves
Date: 7/31/2007
Sometimes even when you seemingly trade an entire squad for one person it still isn't worth it. Then Timberwolves GM Kevin McHale found this out when he traded for the Big Ticket for Al Jefferson, Ryan Gomes, Sebastian Telfair, Gerald Green, Theo Ratliff, two first-round draft picks, and cash considerations. It was the largest number of players (7) traded for one in league history. The trade paid off instantly for the Celts as they won a championship the following season. As for the Timberwolves...they've failed to win more than 24 games in each of the three seasons following the trade. Based on what they've done in the past, they'll probably trade Kevin Love for the entire Laker bench...actually, no, that's too good a deal for them. Maybe it'll be the Knicks bench. #wishfulthinking

16. Cowboys Trade Herschel Walker For 'Chips

Dumbass Move By: Wheelock Whitney, Jr.
Date: 10/12/1989
Initially, this trade may have looked like a lop-sided deal heavily in favor of the Vikings. Looking at it now, things took a huge turn in the Cowboys' favor after they used two of the draft picks given to them on Darren Woodson and Emmitt Smith. One dynasty team later, Dallas has multiple Super Bowl titles to thank for that deal, while Minnesota has two seasons of under 1,000 yards rushing from Herschel Walker.

15. Galácticos

Dumbass Moves By: Florentino Perez
Date: 2000-2007
On paper, Florentino Perez's Galácticos plan, which consisted of adding one superstar soccer player every year, seemed like a genius idea. But then again, there wasn't enough paper in the world to make this scheme work without it having some flaws. Because after a while, the Real Madrid general manager started putting the club in some deep debt that they would have trouble getting out of. We're pretty sure that Perez knew nothing about the phrase "taking a look at the books."

14. Nets Trade Dr. J For $3 Million

Dumbass Move By: Roy Boe
Date: 10/20/1976
New York has been strong arming Jersey for the longest. Sports is no exception. When the NBA and ABA had their merger in 1976, the Nets had to pay a number of fees, one of the biggest being $4.8 million to the Knicks for "invading their NBA territory." Nets owner Roy Boe had already promised Julius Erving a raise in salary but steep fines prevented the team from being able to do so and as a result Dr. J refused to play. The Nets offered Erving to the Knicks in exchange for waving the fee but they refused (FAIL!). Shortly afterward the Sixers offered $3 million for Erving and the Nets had no choice but to take the deal to relieve some financial strain. Soundtrack, please!

13. Mets Trade Nolan Ryan

Dumbass Move By: Bob Scheffing and the New York Mets
Date: 12/10/1971
Yeah, Nolan Ryan was upset with Mets management and did consider retiring from baseball, but that doesn't excuse the epic fail of a deal that New York pulled off with the California Angels. However, all that changed when he left the city that never sleeps and became one of the best pitchers to ever play the game. It's official: The Mets have the worst luck ever! Or they just make ridiculously stupid front offive moves...#keepit100

12. Falcons Give Away Brett Favre

Dumbass Moves By: Jerry Glanville
Date: 2/10/1992
Former Falcons coach Jerry Glanville was once quoted saying that it would take a plane crash to put Brett Favre in a game. FYI: He said this after Atlanta selected Favre in the second round with the 33rd overall pick in the 1991 NFL Draft. After four career pass attempts, Favre bid the ATL adieu and was dealt to the Packers for a 1st round pick. And as they say, the rest is history, or rather, history making because #4 went on to alter the record books. While Jerry has said that he used the trade as a wake-up call for Brett in regards to his off-the-field issues with drinking and partying, let's just say that the only wake-up call was that Glanville should probably never be in charge of making decisions again. #nuffsaid    

11. The Chargers Use No. 2 Pick on Ryan Leaf

Dumbass Move By: Bobby Beathard, Alex Spanos, and the San Diego Chargers
Date: 4/18/1998
The NFL Draft is, and always will be, one of the craziest events in sports. You have future Hall of Famers selected right next to infamous NFL Draft busts and no one really knows who is who quite yet. Unfortunately, San Diego ended up with the latter when they selected Ryan Leaf second overall right after the Colts had picked Peyton Manning. Many analysts praised Leaf for his arm strength while others said Manning's maturity made him better suited for the NFL.

Not only did the Chargers end up drafting one of the worst quarterbacks of all time, it's what they gave up to get him. They originally had the third pick but traded two first round picks, a second round selection, and return specialist Eric Metcalf to Arizona for the second overall pick in the draft. Yes, they gave up all of that to move up one measly spot and assure themselves of getting Leaf. If that weren't enough, they signed him to a $31.25 million contract which at the time included the largest rookie signing bonus ($11.25 million). After his poor performance on the field (four wins over three seasons) and spats with teammates, fans, and the media, the Chargers released him in 2000.

10. "The Midnight Massacre"

Dumbass Move By: Joe McDonald and the New York mets
Date: 6/15/1977
Tom Seaver must've overstayed his welcome in New York. What other reason is there for why the Mets couldn't cough up the extra dough to keep Seaver in blue and orange? On that horrible day known as "The Midnight Massacre," New York traded their best pitcher (three-time Cy Young Award winner) to Cincinnati for four mediocre players. Seaver, who was 7-3 at the time, finished the season at 21-6. Does it make it any crazier that the Mets made Joe McDonald the team Vice President two years after this move? Actually, considering it's the Mets it makes perfect sense.

9. Knicks Sign Allan Houston To $100M Contract

Dumbass Move By: Scott Layden and the New York Knicks
Date: 7/23/2001
No one, and we mean, no one was going to pay Allan Houston anywhere close to a $100 million contract. So why in the world did former Knicks GM Scott Layden want to give Houston that ridiculous deal? And to make matter worst, Houston retired before his contract came to an end, and in 2007, he was second-highest paid player in the NBA ($20.7M) despite not playing in a single game! It's no wonder that the Knicks and many other New York teams take up the majority of spots on this list.

8. Islanders Use Their 2000 First Pick On Rick DiPietro

Dumbass Move By: Mike Milbury and the New York Islanders
Date: 6/24/2000
When Mike Milbury made Rick DiPietro the first goaltender ever drafted first overall in NHL history, it only added to the infamous legend of "Mad Mike." With that pick, Milbury missed out on stars such as Dany Heatley, Marian Gaborik, Scott Hartnell, and Ilya Bryzgalov for a guy that is now referred to as "Rickety" DiPiertro (a jab at how injury prone he has been). He also traded away another future All-Star in Roberto Luongo in the process. All that for someone who's played in just 39 games over the last three seasons. SMH. Seriously, by stepping down as GM, Milbury made his best decision when thinking about the Islanders' future. 

7. Bill DeWitt Trades Frank Robinson

Dumbass Move By: Bill DeWitt
Date: 12/9/1965
Being a general manager means going with your gut, which is exactly what DeWitt did when he traded Frank Robinson to the Orioles for two pitchers and a minor league outfielder. DeWitt was under the assumption that Robinson was an "old 30" and past his prime. How did that turn out? The Orioles newest acquisition won the Triple Crown and American League MVP in his first season. The Big Red Machine with Frank Robinson? Wouldn't have been fair.

6. Knicks Acquire Eddy Curry Via Trade

Dumbass Move By: Isiah Thomas
Date: 10/3/2005
The Knicks x financial problems just seem to go hand-in-hand. Isiah Thomas took a huge chance on Eddy Curry by trading for him with the Chicago Bulls. The deal resulted in the Knicks owning Curry $60 million over six years. As any Knicks fan knows, that gamble didn't pay off as Curry turned into one of the highest-paid players to ever warm up a seat on the bench. One of his lowest points came in the 2008-09 season when he only played in three games and scored five points total for the season.

5. Raiders Pick JaMarcus Russell

Dumbass Move By: Al Davis
Date: 4/28/07
It's not that the Raiders paid Russell tens of millions of dollars to cripple the franchise. It's not the soul-sucking hundred yard stare he used to give on the sidelines. It's not even the fact that he's the WORST QUARTERBACK IN THE HISTORY OF THE LEAGUE that makes fans of the Silver and Black cringe whenever they hear his name. No, it's the names that came after Russell on that fateful April afternoon: Calvin Johnson, Adrian Peterson, Patrick Willis, Darrelle Revis, Sidney Rice, LaMarr Woodley (should we stop now?).

4. Hornets Trade Away Kobe Bryant

Dumbass Move By: George Shinn and the Charlotte Hornets
Date: 7/11/1996
It's hard to imagine the Black Mamba in anything but purple and gold but he was a Hornet...if only for a few days. In one of the biggest NBA Draft fails, the Hornets agreed to trade their draft selection to the Lakers before making their pick. Only minutes before the selection, Charlotte was told to pick Bryant. He was selected and only a few days later traded to the Lakers for Vlade Divac and cigarettes. Lots and lots of cigarettes. SMH.

3. The Lions Hire Matt Millen

Date: 1/8/2001
Dumbass Move By: William Clay Ford Sr. and the Detroit Lions
You were wondering where all the Lions moves were, huh? We had to go back to the source on this one. How do fix up an ailing franchise? According to the Detroit Lions, you go out and hire a guy with no prior front office experience. In 2001 the team's front office decided to go with former linebacker turned commentator Matt Millen in an attempt to right Detroit's sinking ship. To no one's surprise, the Lions continued on a decline and the Millen experiment ended after SEVEN YEARS! Because it only took seven consecutive years of losing and a record of 31–81 and .277 winning percentage (worst in the league son!) to figure out dude needed the boot.

2. The Trail Blazers Draft Sam Bowie

Dumbass Move By: The Portland Trail Blazers
Date: 6/19/1984
If the Trail Blazers had access to a time machine, the first thing they would do is travel back to the 1984 NBA Draft and make the right choice. When Portland had the second overall pick that year, they went with Kentucky forward Sam Bowie instead of that North Carolina guard, Michael Jordan. We won't insult your intelligence by giving you a summary of how Bowie's career panned out compared to MJ.

1. The Red Sox Trade Babe Ruth

Dumbass Move By: Harry Frazee and the Boston Red Sox
Date: 1/3/1920
Babe Ruth wanted a raise. That's all. The Red Sox refused to give him what he was asking for ($20,000), so Boston gave Ruth to the Yankees for $125,000. We all how that turned out, right? *cough Curse cough* 86-year championship drought x losing arguably the best baseball player of all time = Dumbest front office move of all time.