As the calendar winds down on 2008, we can look back at the year in sports and evaluate the transactions teams made. In some instances teams had hits, and in other cases we can see where teams missed. And there were certainly a number of misses this year. Some were made by the usual suspects, such as the Oakland Raider and Detroit Lions. Some were made by unusual ones as well.

Looking across all sports, here’s what we at Gunaxin deem the worst sports transactions of the year. The only rule to qualify is that the transaction (be it a trade, draft pick, or free agent signing) had to be executed sometime in 2008. The rankings were evaluated by the magnitude of damage to the respective team. Certainly some moves didn’t exactly pan out as hoped, Pac-Man Jones comes to mind, but they didn’t cost much either so little damage done. The deals on this list will haunt teams for years, either by wasting money, taking up salary cap space, and/or simply by the loss of talent involved (or lack of talent received).

And no Brett Favre on this list. For as much as the Packers have fallen off, Aaron Rodgers actually has had a good year and currently has better numbers than Favre (who leads the league in interceptions). There’s a lot more wrong with the Packers than quarterback play. I’ll grant you that Rodgers may not be better than Favre, and maybe the Packers would have won more games with Favre, but it’s not a huge difference. Besides, the Packers got good value from the Jets, so it wasn’t a horrible trade. Here are ten transactions that were horrible, however. In the words of Arrested Development, “I think I’ve made a huge mistake!”:

10. Cleveland chooses poorly with Derek Anderson (February 2008)

I’ll grant you that the entire Cleveland Browns team imploded this season, but Anderson has the 2nd worst QB in the NFL by rating, narrowly edging out the beaten down Matt Hasselbeck. To illustrate how bad that is, he ranks below a couple of rookies, and whatever bodies are quarterbacking the Chiefs, Raiders, Rams, and Bengals these days. Ouch. So why does Anderson’s crappiness suck so much? The Browns rewarded him in the off-season to the tune of three-years and $24 million dollars.

Obviously that’s a bad contract, made worse by the reported $7 million signing bonus. And yet the problems go deeper. Last offseason the Browns had a decision to make, pay Anderson or trade him and go with second year quarterback Brady Quinn. They decided to pay Anderson, which meant they had to play him. That directly hurt the development of Quinn, who rode the bench for most of the season. It also meant the team passed up landing multiple draft picks for dealing Anderson. And given his poor play and large contract, most likely the Browns will part ways with Anderson in the offseason without getting any compensation. That’s a tough pill to swallow.

Most disappointing is that what happened with Anderson isn’t exactly surprising. Young non-rookie quarterbacks who finally get their first sustained playing time can initially do very well. Not all of them, of course, but many of them do. And then, a few weeks into their stint as a starter, their numbers take a nosedive. Why? It happens when other teams get a few games of them on film, spot tendencies, and start to take away the things that a particular quarterback likes. I think Scott Mitchell pioneered this principle more than a decade ago. Any team should have been very hesitant to give a lot of money to Anderson based on his 2007. And there’s still more red flags.

Anderson has a strong arm, but has never shown great accuracy at any level. Not in college, not in 2007, never. That’s basically Kyle Boller, and that’s not a recipe for NFL success. Anderson simply isn’t consistent enough from game to game, or even throw to throw. Sure, the fact Braylon Edwards has hands of stone won’t help anyone’s completion percentage, but it doesn’t explain all the problems Anderson has. Cleveland should have taken the draft picks and gone with Quinn. It wouldn’t have solved all their problems, but at least they’d be loaded with picks.

9. The Clippers steal Marcus Camby (July 2008)

This past summer the Denver Nuggets traded Camby to the Los Angeles Clippers for the option to swap second round draft picks in the 2010 NBA Draft. Now you have to understand that second round picks are fairly worthless by NBA standards. They are routinely sold or otherwise given away, and the players chosen rarely make an impact in the league. This trade wasn’t even good enough for a whole second round pick, only an option to swap picks. That’s just giving away a player. Camby’s worth more that that. Heck, pretty much anyone is worth more than that.

Yes, I’ll concede that Camby is injury prone, a tad expensive ($10 million for each of the next two seasons), and on the down slope of his career. But this is a guy that won the NBA Defensive Player of the Year Award in the 2006-’07 season and was NBA All-Defensive First Team the past two seasons. That’s a valuable player. In 79 games last year he led the league in blocks and averaged 13.1 rebounds. Any team would love to have him and that kind of defensive presence. Instead the Nuggets gave him away, in a desperate attempt to avoid the luxury tax.

Considering the money thrown around to mediocre free agents, how the Nuggets got so little for Camby is just sad. The Nuggets were even a playoff team last season, but decided to sabotage this season before it started. They wanted to cuts costs, found someone with salary cap space, and then bent over as that team named it’s price.

Why not keep Camby and trade him later in the season when teams are looking for a stretch drive acquisition? Why not actually plan out your spending better and not make panic trades? Who knows? The Nuggets don’t.

8. New York Rangers are snookered by Wade Redden (July 2008)

There were a ton of questionable signings in hockey this summer (Jeff Finger, Brian Campbell, Ron Hainsey, etc…) as teams threw around money like it was going out of style. But the winner for worst contract appears to be Wade Redden. Once upon a time, Redden was a pretty good player. He even represented Team Canada in the Winter Olympics. But something happened to Redden, his play began to slip, and he was all but run out of Ottawa last spring.

Undeterred, the Rangers signed him to a six-year, $39 million contract. That’s a perfect example of being rewarded for diminishing returns. The term of six years is absolutely stunning as it runs until Redden is 37 and averages 6.5 million a year, one of the higher annual salaries in the entire league. There’s simply no way Redden can justify the contract without finding a fountain of youth. His play so far hasn’t been encouraging as he’s been questionable defensively, invisible offensively, and has contributed his fair share to a poor power play. What’s worse? Because the NHL uses a salary cap, the wasted money may come back to haunt the Rangers. As their young players develop and hit free agency, will they have the cap room to retain them? They’re already pushing up against the cap, a factor that may have hurt in their recent pursuit of Mats Sundin.

7. Minnesota dumps Johan Santana for a random box of parts (January 2008)

This one stings doubly for the Twins. First, Detroit and Cleveland were expected to dominate the AL Central, but it was the Twins who tied for the division win and headed for a playoff. Maybe they could have used an ace pitcher like Santana against the White Sox? Could it have made the difference in winning a World Series? Unknown, but it couldn’t have hurt.

Second, the team really didn’t get a good return from the Mets. It’s actually puzzling that they settled for what they did. This was arguably the best pitcher in all of baseball. All the big name franchises were interested and placed bids. Allegedly, the Twins asked for players like Phil Hughes from the Yankees and Jon Lester from the Red Sox. But the mediocre packaged they settled for has no prospect of that caliber.

Only Carlos Gómez was considered a pretty good prospect, but not nearly the level of Hughes or Lester. Plus Gómez is very, very raw. As you saw in his rookie season he showed speed and glove work, but his poor batting actually made him below replacement level. Of the other three players acquired in the deal (pitchers Philip Humber, Deolis Guerra, and Kevin Mulvey), only Mulvey was decent in 2008. Even more puzzling was how many pitchers the Twins acquired. If there’s one thing the Twins are already very deep in, it’s young pitching. They could have used this trade as an opportunity to fill the void the organization has with position players, both in the minors and majors. It’s simply the wrong kind of package for them.

One could argue this is the best Minnesota could do given the market. After all, Santana was set to be a free agent after the season. However, only a few months later the Indians got a much better haul for three months C.C. Sabathia, including true elite prospect Matt Laporta. In this list of top prospects for 2009, LaPorta ranks 7th in all of baseball. None of the players the Twins received cracks the Top 100. That suggest that the Twin sold real low on Santana. To add insult to injury, the Twins signed Liván Hernández to fill the innings Santana pitched and Hernández was awful. This really should have gone a lot better for the Twins.

6. Avery’s sloppy seconds come back to haunt the Dallas Stars (July 2008)

Noted agitator Sean Avery signed a four-year deal for a guaranteed $15.5 million with the Dallas Starsin the offseason. He’d been a roommate of current Stars co-general manager Brett Hull in the past, so maybe he was signed for some of the wrong reasons. It’s no secret that Avery is a volatile personality, annoying those in his own dressing room as much as his opponents on the ice. Because he is highly skilled at rubbing people the wrong way, he’s a risky signing for any team.

To date, Avery’s on-ice performance for Dallas has been largely poor. He has scored just three goals, a poor total for someone making nearly four million a season. And that was before an incident involving remarks directed towards Flames’ defense man Dion Phaneuf. Phaneuf is dating Avery’s ex-girlfriend Elisha Cuthbert, which prompted Avery to exclaim, “I am going to say one thing. I am really happy to be back in Calgary. I love Canada. I just want to comment on how, it has become a common thing in the NHL for guys to fall in love with my sloppy seconds. I do not know what that is about, but enjoy the game.” The comment also may encompass Kings forward Jarret Stoll, who is dating another of Avery’s ex-girlfriends, Rachel Hunter.

After the remarks, the NHL suspended him indefinitely for “conduct detrimental to the league or the game of hockey.” He and the Stars soon parted ways, as on December 14 the Stars announced that Avery would not return to the team. In addition to the remarks, his play was a source of frustration to his teammates and he had alienated himself to his teammates. As of now, the team is actively pursuing options to permanently rid themselves of Avery. $15.5 million for three goals? That’s money well spent!

5. Robbie Keane goes to Liverpool for a lot of money (July 2008)

Robbie Keane was billed as the perfect attacking partner for Fernando Torres when he joined Liverpool in a transfer from Tottenham at a cost of £20.3 million. Soccer fans were skeptical, as Keane’s never been viewed as one of the upper echelon elite footballers.

True to expectations, it has not gone well. In 23 appearances for Liverpool, Keane has rarely completed a match, and has scored just twice in the Premiership play (4 times overall). Now Keane is rumored to be up for sale this coming transfer period at half the price Liverpool played. A loss of 50% of value in mere months? Sounds like the stock market of late. Robbie Keane is living proof that the cliché you always get what you pay for is not accurate.

4. Raiders try the DeAngelo Hall Experience (March 2008)

Picking on the Oakland Raiders seems like beating a dead horse, but in this case it has to be done. Their off-season was simply a complete mess. Here are some of the terrible contracts they gave out which didn’t crack this list: they signed DT Tommy Kelly for 7 years, $50 million with $18 million guaranteed; S Gibril Wilson for 6 years, $39 million with $16 million guaranteed; and gimpy kneed WR Javon Walker for 6 years, $55 million with $16 million guaranteed. That’s a who’s who of bad contracts.

And yet there’s something even worse than those signings. In March, Oakland managed to trade second and fifth round picks to the Atlanta Falcons for the rights to DeAngelo Hall. Now the Raiders suck, so the second round pick was a pretty high selection. That’s something they might have used on someone good (well they’re the Raiders so they probably would have blown the selection). Because the Raiders had already traded their third round pick, it left them with only one selection on day one of the NFL draft. That’s not a recipe for success for a rebuilding squad. And yet it gets worse.

The team immediately signed Hall to a seven year, $70 million dollar contract with a reported $24.5 million guaranteed. That might not be terrible move if Hall was good. But Hall got toasted repeatedly early in the season, and was released after eight games. Seriously, just a half a year. A couple draft picks and all that money for a whooping eight games for a terrible team. Nice move Oakland!

3. Dallas downgrades Devin Harris for Jason Kidd (February 2008)

The trade that almost didn’t happen. I’m sure Dallas fans wish it didn’t. After Devean George threw a wrench into the original trade, the teams continued to negotiate and arrived at this debacle. The revised version reportedly cost the Mavericks an additional 11 million dollars. It sent Jason Kidd, forward Malik Allen, and swing man Antoine Wright to Dallas in exchange for Devin Harris, center DeSagana Diop, swing man Trenton Hassell, guard Maurice Ager, forward Keith Van Horn, first-round draft picks in 2008 and 2010, and $3 million in cash.

Now Kidd was a great player, and while he remains a decent one, he is a shadow of his former self. His offense is eroding to problematic levels and he is plagued by defensive problems, something that doesn’t always show up in the box scores. At 35 he’s slipping, something that happened to players like Gary Payton and Tim Hardaway at similar ages. And he’s getting paid $21.3 million this season.

But the real problem is that the 25 year old Devin Harris is already the better player, averaing 24.5 points and 6.6 assists this season for the Nets. For the Mavericks, a team in must win now mode, this is just further setting them back for winning a championship. Had they kept Harris, they might be competing for a championship. Without him, they’re just another team.

2. Orioles fleece the Mariners for Erik Bedard (February 2008)

Here’s the full trade: Bedard for George Sherrill, Adam Jones, Chris Tillman, Tony Butler, and Kameron Mickolio. Now here’s the scorecard after one season. Sherrill made the AL All-Star team, Jones developed into an exciting young center fielder who will only be 23 next season, Tillman is considered one of the best prospects in baseball (#18 on this list, also see John Sickel’s report), and Bedard pitched 81 meaningless innings for one of baseball’s worst teams while tearing his labrum.

Seattle’s first problem was thinking they were better than they were. They viewed Bedard as the final piece to being a contender, but they really weren’t all that close. The next problem is that Bedard got hurt, and labrum tears are pretty much the worst injury a pitcher can get. Sure, there’s some bad luck involved with pitcher injuries, but it’s not like Bedard didn’t have warning signs. He’s already had Tommy John surgery and has never topped 200 innings in a season. The guy has always seems to be nicked up.

Worse yet, Bedard’s a free agent after the 2009 season. In the event he can come back and is healthy next year, he’ll probably just leave as a free agent for greener pastures. Meanwhile the Orioles can build around the talented Tillman and Jones for years, and everything else they get out of the deal is just gravy. In fact, the folks over at U.S.S. Mariner have dubbed this the official worst trade in Mariners history. That’s saying something coming from a team that sent Ken Griffey Jr. and Randy Johnson packing in the middle of their illustrious careers.

1. Grizzlies trade Pau Gasol for a bunch of magic beans (February 2008)

I guess there was something in the air last February, as there were some brutal trades executed. In this one the Memphis Grizzlies gave away their best player for pretty much nothing. Okay, so Gasol might be a little overpaid and a tad soft, but he’s productive, in the prime of his career, and helped led Spain to a silver medal in the Summer Olympics.

The official haul was that the Lakers gave up Kwame Brown, rookie Javaris Crittenton, the rights to Marc Gasol, and two first-round draft picks. Marc is Pau’s brother and pretty much the only valuable piece in the deal. Because the Lakers are so good the first round picks will end up being fairly low in the draft, and the Phoenix Suns and other teams have literally just sold picks better than this. Am I to believe this was literally the best that could be obained? Only a few months before the deal, Bill Simmons rated Gasol as the 39th most valuable commodity in the league. What the hell happened here? The Grizzlies might as well have kept Gasol and had actual talent on their roster.