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The Boldest Offseason Moves of the 2000s

Nick DimengoMar 15, 2015

In case you haven't noticed, the NFL offseason has gotten off to quite the bang.

In addition to the Philadelphia Eagles doing, well, something crazy each day, there have been a ton of trades and big-money deals thrown at a number of different players.

With so much action and players on the move, it can be difficult to keep track of everything.

While many of this year's moves have been shocking and unexpected, I decided to dive into some of the boldest moves in all of sports since the turn of the century, reminding you of some unique deals that have gotten done since 2000.

Jon Gruden Traded to Tampa Bay Buccaneers (2002)

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Anytime two organizations trade a head coach, it's bold.

Although the Oakland Raiders had made the playoffs in three of four seasons with Jon Gruden as their leader, the team grew tired of missed opportunities once the postseason began, failing to make it to the Super Bowl.

So when the Tampa Bay Buccaneers offered two first-round picks, two second-round picks and $8 million in cash for the guy, the Raiders figured it was time to cut bait and move in a different direction.

Taking over for the fired Tony Dungy, Gruden paid off immediately for Tampa Bay, as he didn't just lead the team to a Super Bowl win in his first season but did so by defeating his former team in the process.

Talk about your all-time backfires.

Kevin Love Traded to Cleveland Cavaliers (2014)

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Although the true measure of this trade won't be judged unless the Cleveland Cavaliers win an NBA title with him, when Cleveland acquired Kevin Love from the Minnesota Timberwolves after the return of LeBron James, it was a message to the team and its fans—we're going for it all.

Rather than wait for No. 1 overall pick and perceived future star Andrew Wiggins to develop, Cleveland sent 2014's top selection to Minny along with the No. 1 overall pick in 2013, Anthony Bennett.

While James said in his "I'm Coming Home" letter that he had to be patient, the Cavs front-office knew better, bringing the three-time All-Star K-Love aboard to form a Big Three alongside Bron and Kyrie Irving.

Alexei Yashin Traded to New York Islanders (2001)

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After Alexei Yashin sat out an entire season as a stand for a new contract, the Ottawa Senators gave in and decided to unload the talented center.

Averaging 91 points in 1998-'99 and 2000-'01, Yashin never again saw the same success after getting dealt.

While it was unsure how the move would work out, the Senators received Zdeno Chara, Bill Muckalt and a first-rounder who turned out to be Jason Spezza from the New York Islanders, while the Isles handed Yashin a terrible deal worth $87.5 million over 10 years, eventually buying him out due to lack of production.

For Ottawa, the three players developed into solid pieces, with Chara becoming a multiple All-Star and one of the league's top defensemen.

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Josh Hamilton Traded to Texas Rangers (2007)

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There have been a number of risky acquisitions in major league history, but the one that brought Josh Hamilton to the Texas Rangers might be the biggest gamble since the turn of the century.

While J-Ham was the first overall selection in the 1999 draft, his well-documented drug problems off the field made teams wary of giving up too much for him when the Cincinnati Reds dangled him as trade bait.

He quickly erased any concerns in Texas, though.

Leading the American League in RBI his first season with the Rangers, Hamilton made the All-Star Game in each of his five seasons in Big D, helping the team reach two World Series trips and earning the league MVP in 2010.

The Rangers gave up on Edinson Volquez—who went 30-18 with a 4.17 ERA in four seasons with Cincy—but absolutely won the trade by taking a chance on Hamilton.

Doc Rivers Traded to Los Angeles Clippers (2013)

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With the Boston Celtics set for a rebuilding project after trading away the last two pieces of their Big Three, the team decided to cut ties with the head coach who led them to two NBA Finals appearances and one championship, Doc Rivers.

While it was a fairly simple plan from the C's side—they received the Los Angeles Clippers' first-round pick in 2015—to see the Clips be so aggressive in obtaining a championship-level leader was a bit shocking.

After all, these were the same Clippers who had been so cheap and inconsistent under former owner Donald Sterling.

Thankfully, the move has worked out well. Doc led the team to the postseason last year and is set for another run this season. Following the Sterling debacle in May 2014, the team is now under new ownership that brought new energy.

Washington Redskins Trade to Draft Robert Griffin III (2012)

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It's not so much that the Washington Redskins made a bold move by selecting former Heisman Trophy winner Robert Griffin III second overall in the 2012 NFL draft. It's that they gave up a king's ransom in order to get in the position to do so.

With the St. Louis Rams locked into the No. 2 slot and without a need for a quarterback after drafting Sam Bradford No. 1 overall two years prior, they were open for business to shop the pick.

And did they ever get an offer.

Receiving three first-rounders and a second-round pick from the Skins, the team traded down to the sixth spot, giving Washington its quarterback of the future.

While RGIII won the league's Offensive Rookie of the Year and guided the team to the playoffs, he has been inconsistent since, battling injuries and going back-and-forth as the starter.

You have to give Washington credit, though; giving up so much to get the guy it targeted all along was a risk most teams wouldn't take.

LeSean McCoy Traded to Buffalo Bills (2015)

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With the signing of free-agent running back DeMarco Murray, the Philadelphia Eagles not only found a replacement for the recently traded LeSean McCoy but also hit a division rival—the Dallas Cowboys—by taking a key offensive weapon.

Still, the decision by Chip Kelly to ship McCoy to the Buffalo Bills in exchange for linebacker Kiki Alonso was one that, just last week, had Philly fans wondering about the head coach's plan.

In the past four seasons, McCoy has rushed for the second-most yards in the NFL, averaging 1,268 per season.

While Murray brings a different element to the Eagles next season and Alonso, if healthy, can be a key piece on the defensive side of the ball, getting rid of an All-Pro back doesn't always end up working out so well.

In this case, it seems to have so far, though.

Giancarlo Stanton Signs for the Biggest Sports Contract in History (2014)

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No matter how you spin this, the Miami Marlins took a huge gamble by paying star outfielder Giancarlo Stanton the biggest contract in American sports history this past offseason.

There's no denying his value and talent, but with Stanton working his way back from a devastating eye injury after getting hit in the face by a pitch, one can't help but be worried about how he'll respond during live at-bats.

Should the two-time All-Star return to his normal form—which has been 39 home runs and 102 RBI per year since breaking into the big leagues in 2010—then the Marlins will be smiling for the next 13 years, happy with rolling the dice on Stanton.

Teemu Selanne and Paul Kariya Sign with Colorado Avalanche (2003)

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Traditionally, a small-market team like the Colorado Avalanche isn't going to break the bank by spending on the top free agents.

In the 2003 offseason, though, the Avalanche went against routine by bringing in two of the top players available that year, Teemu Selanne and Paul Kariya.

Familiar with each other from their days with the Anaheim Ducks, the two All-Stars took less money to try to bring a title back to the Mile High City.

Though bold, the strategy didn't work.

Sure, the team made the postseason after earning the No. 4 seed in the Western Conference, but Colorado got bounced in the second round by the San Jose Sharks, falling short of its goal to hoist the Stanley Cup.

Both Selanne and Kariya moved on after the one season together, with both having down years in Avs sweaters.

This is a reminder that, while big-name players gather headlines, winning the offseason doesn't always translate to winning in real life.

Ken Griffey Jr. Traded to Cincinnati Reds (2000)

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This almost never happens: Because of a trade demand back to his hometown club, the Seattle Mariners dealt a once-in-a-generation player like Ken Griffey Jr.

Yet, back in 2000, that's exactly what the Mariners were forced to do after Junior wanted to head to the Cincinnati Reds, where he grew up after his dad had starred for the team. 

Getting rid of Griffey was a move that no general manager would want to have on his resume, but one of the players the M's received, Mike Cameron, turned out to be quite the replacement.

Cameron lacked Griffey's power, but he gave the Mariners a major league-ready starter who enjoyed his best big league years in the Pacific Northwest.

Bowing to the trade demand was difficult. Seeing a guy like Cameron make an All-Star Game and help the M's get to the playoffs two of his four years helped relieve some of the pain.

Shaquille O'Neal Traded to Miami Heat (2004)

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Winning three NBA titles in his eight seasons with the Los Angeles Lakers, center Shaquille O'Neal just couldn't exist with fellow superstar Kobe Bryant. There was more drama than a Hollywood movie between the two players back in 2004.

With the Lakers brass deciding to go all-in with the younger Bryant, the front office decided that, following a Finals loss to the Detroit Pistons, it was time to wave goodbye to Shaq.

The Lakers traded him to the Miami Heat in 2004 for Caron Butler, Brian Grant, Lamar Odom and a first- and second-round pick, and the Heat happily welcomed the most dominating player since Wilt Chamberlain to South Beach.

Teaming up with a new sidekick, budding superstar Dwyane Wade, O'Neal helped lead the Heat to an NBA championship in his second season with the team, earning his fourth career title and making Heat President Pat Riley look pretty smart by acquiring the Big Aristotle even though he was 32 years old.

Randy Moss Traded to New England Patriots (2007)

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When the Oakland Raiders decided to part ways with former All-Pro wide receiver Randy Moss in 2007 by sending him to the New England Patriots for a fourth-round pick, I'm not sure they believed he would have such an impact on the Pats.

Unhappy with the losing ways in Oakland, Moss merely needed a winning culture to get back on track, proving that the risk the Patriots took was more than a solid call.

Catching 98 passes for 1,493 yards and setting a single-season record with 23 touchdown grabs, Moss helped New England go through the regular season undefeated and, ultimately, earn a berth in the Super Bowl—where we all know they got upset by the New York Giants.

With the pick, the Raiders took cornerback John Bowie, who appeared in just five games and lasted two seasons in the league. This is a move that the Pats were certainly happy with—even if Moss did end up getting traded in 2010 after some displeasure with the front office in Foxborough.

Drew Brees Signs with New Orleans Saints (2006)

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Quarterback Drew Brees might be a stud these days, but before signing with the New Orleans Saints in 2006, he was a guy who had some serious question marks when he hit the free-agent market.

Proving himself capable of being a starter in the league after a slow start in his first couple of seasons, Brees suffered a serious shoulder injury just months before he hit the market, which caused a number of teams to rethink if he was worth the risk.

As the Miami Dolphins and then-head coach Nick Saban debated if they wanted to invest so much in a fragile player, the Saints swooped in and gave Brees a deal for six years and $60 million.

Their reward? Brees gave them 43,685 passing yards, 316 touchdown passes and a Super Bowl victory in his nine years in the Big Easy, making the risk more than worth it.

Kevin Garnett and Ray Allen Traded to Boston Celtics (2007)

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Talk about going all-in, huh?

With the Boston Celtics missing out on the postseason in consecutive seasons in 2005 and 2006, the front office thought a bold overhaul was worth considering, jumping at the chance to snag two future Hall of Famers.

First, the C's made a trade with the Seattle SuperSonics to acquire sharpshooter Ray Allen for a few players. They didn't stop there, agreeing to a deal with the Minnesota Timberwolves for perennial All-Star Kevin Garnett about a month later.

Pairing the two with another superstar, Paul Pierce, gave Boston its Big Three, and the trio led the team to an NBA title in their first year together by defeating the hated Los Angeles Lakers.

In their five seasons together, the trio advanced to at least the second round of the playoffs each year, losing in their only other Finals trip during the 2009-10 season.

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