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JACKSONVILLE, FL - OCTOBER 03:  Quarterback Peyton Manning #18 of the Indianapolis Colts throws while taking on the Jacksonville Jaguars at EverBank Field on October 3, 2010 in Jacksonville, Florida.  (Photo by Marc Serota/Getty Images)
JACKSONVILLE, FL - OCTOBER 03: Quarterback Peyton Manning #18 of the Indianapolis Colts throws while taking on the Jacksonville Jaguars at EverBank Field on October 3, 2010 in Jacksonville, Florida. (Photo by Marc Serota/Getty Images)Marc Serota/Getty Images

The 10 Greatest Contract Years of All Time

Adam LazarusOct 4, 2010

Technically, Peyton Manning is in a "contract year" this season: he becomes a free agent after 2010. We all know that the Colts will re-sign him no matter if he threw 50 interceptions the remainder of the season.

But ever since the advent of free agency, the "contract year" has been vital to a player boosting his perceived value on the open market.

DeAngelo Williams is a free agent next season and how well he finishes the season up will be critical in who looks at signing him next spring.

If he puts up another 1,500-yard season and stays healthy, he'll earn big dollars. An injury or a big drop-off in numbers will likely cost him millions.

That is usually the Catch-22 for players in their contract year. Here's a look back at some of the players who took advantage of their soon-to-be free agent status and were able to cash in.

No. 10: LeBron James, 2009-10

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MIAMI - SEPTEMBER 27:  LeBron James #6 of the Miami Heat pose for photos during media day at the Bank United Center on September 27, 2010 in Miami, Florida.  (Photo by Marc Serota/Getty Images)
MIAMI - SEPTEMBER 27: LeBron James #6 of the Miami Heat pose for photos during media day at the Bank United Center on September 27, 2010 in Miami, Florida. (Photo by Marc Serota/Getty Images)

No matter what, LeBron was going to get a max deal in the summer of 2010. So it’s difficult to argue that he was in a “contract year” in the way we usually understand it.

Still, he played the 2009-10 as a soon-to-be free agent and turned in one of the great seasons in recent NBA history. He averaged more points than he did in his 2008-09 MVP season posted 8.6 assists per game and shot an incredible (for a guard) 50 percent from the field.

He definitely came up short in the post-season, especially late against the Celtics. Nevertheless, it was a fantastic season.

No. 9: Manny Ramirez, 2000

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Manny Ramirez #24 of the Cleveland Indians swings at the ball during the game against the Chicago White Sox at the Jacobs Field in Cleveland, Ohio. The White Sox defeated the Indians 3-6.
Manny Ramirez #24 of the Cleveland Indians swings at the ball during the game against the Chicago White Sox at the Jacobs Field in Cleveland, Ohio. The White Sox defeated the Indians 3-6.

Manny’s best season in a Cleveland uniform—maybe in his entire career came in 1999. He hit 44 homers and totaled a whopping 165 RBI. The following season, 2000, was his contract year in Cleveland.

Despite missing 44 games, he still hit 38 home runs and set career highs in batting average and slugging percentage. Manny signed a huge contract with the Red Sox following the season and of course the rest is history.

He and Big Papi were the power hitting tandem that brought Boston two World Series titles in four years.

No.8: Tracy McGrady, 1999-2000

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23 Apr 2000: Vince Carter #15 of the Toronto Raptors shakes hands with teammate Tracy McGrady #1 during round one of the NBA Playoffs against the New York Knicks at the Madison Square Garden in New York. The Knicks defeated the Raptors 92-88.   Mandatory
23 Apr 2000: Vince Carter #15 of the Toronto Raptors shakes hands with teammate Tracy McGrady #1 during round one of the NBA Playoffs against the New York Knicks at the Madison Square Garden in New York. The Knicks defeated the Raptors 92-88. Mandatory

In his third and final season with the Toronto Raptors, Tracy McGrady began to show the rest of the NBA why he was worthy of being a Top 10 draft pick right out of high school.

He started fewer than half of the Raptors games that year but still managed 15.4 points per game and, along with Vince Carter, helped Toronto into the post-season for the first time ever.

The Orlando Magic signed McGrady in the summer of 2000 and he immediately became one of the league’s premier scorers.

Had it not been for his breakout season a year earlier, he might have remained in the shadow of Vince Carter.

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No. 7: C.C. Sabathia, 2008

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PHILADELPHIA - OCTOBER 02:  CC Sabathia #52 of the Milwaukee Brewers delivers in Game 2 of the NLDS Playoff against the Philadelphia Phillies  at Citizens Bank Ballpark on October 2, 2008 in Philadelphia, Pennsylvania  (Photo by Jeff Zelevansky/Getty Imag
PHILADELPHIA - OCTOBER 02: CC Sabathia #52 of the Milwaukee Brewers delivers in Game 2 of the NLDS Playoff against the Philadelphia Phillies at Citizens Bank Ballpark on October 2, 2008 in Philadelphia, Pennsylvania (Photo by Jeff Zelevansky/Getty Imag

Sabathia won the Cy Young award in 2007 but, entering his contract year the next season, he did not pitch particularly well for the Indians. So, as they did with Bartolo Colon in 2000 and would do with Cliff Lee the following seasons, the Indians traded Sabathia in order to get something before he bolted in free agency.

Now a big lefty who can eat up innings and is in the prime of his career is going to fetch a lot of money on the open market anyway. Especially from the New York Yankees.

But in case skeptics wanted to question Sabathia’s big-game abilities, he proved them wrong during the second half of the 2008 season.

His 11-2 record and 1.65 ERA helped the Brewers clinch their first post-season spot in a quarter century. When the Brewers absolutely needed a win on the final day of the regular season, Sabathia surrendered just four hits and one run in a victory over the Cubs.

That must have clinched it for the Yankees, who signed Sabathia to a $161 million deal a few months later.

No. 6: Dana Stubblefield, 1997

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4 Jan 1997:  Defensive tackle Dana Stubblefield of the San Francisco 49ers stands on the sidelines during a playoff game against the Green Bay Packers at Lambeau Field in Green Bay, Wisconsin.  The Packers won the game 35-14. Mandatory Credit: Jonathan Da
4 Jan 1997: Defensive tackle Dana Stubblefield of the San Francisco 49ers stands on the sidelines during a playoff game against the Green Bay Packers at Lambeau Field in Green Bay, Wisconsin. The Packers won the game 35-14. Mandatory Credit: Jonathan Da

The big defensive tackle was a great run stopper and pass rusher for the championship contending 49ers teams of the mid-1990s. And he was already a two-time Pro Bowler by the time his contract had just one year left prior to the 1997 season.

But Stubblefield stepped his play up to a new level in 1997. Despite losing Jerry Rice to an injury very early in the season, the 49ers won the NFC West and came within a game of the Super Bowl. San Francisco boasted the league’s third best scoring defense.

Stubblefield was rewarded with a third Pro Bowl spot, a first team All-Pro selection and the NFL Defensive Player of the Year award.

A free agent that offseason, Stubblefield signed with the Washington Redskins, where he and Big Daddy Dan Wilkinson became the league’s most overpriced and overrated pair of interior defensive lineman.  

No. 5: Juan Gonzalez, 2001

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Juan Gonzalez #22 of the Cleveland Indians hits a solo hopme run in the second inning against the Seattle Mariners during game four of the American League Division Series at Jacobs Field in Cleveland, Ohio, October 14, 2001. DIGITAL IMAGE  Mandatory Credi
Juan Gonzalez #22 of the Cleveland Indians hits a solo hopme run in the second inning against the Seattle Mariners during game four of the American League Division Series at Jacobs Field in Cleveland, Ohio, October 14, 2001. DIGITAL IMAGE Mandatory Credi

The two-time MVP was shipped to Detroit prior to the 2000 season where he was not nearly as productive as he had been the previous decade.

In that contract season, a huge drop off in home runs and batting average cost him a chance at a lucrative, long-term deal that the Texas Rangers refused to give him a year earlier.

So Gonzalez signed a one-year, $10 million contract to play with Cleveland and he immediately returned to top form. As the right field replacement for Manny Ramirez, he hit 35 home runs, knocked in 140 runs and posted a .325 average.

For some reason, the Rangers brought Gonzalez back the following year and he never again approached All-Star numbers.

No. 4: Albert Haynesworth, 2008

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NASHVILLE, TN - JANUARY 10:  Defensive tackle Albert Haynesworth #92 of the Tennessee Titans looks on after losing to the Baltimore Ravens 13-10 during the AFC Divisional Playoff Game on January 10, 2009 at LP Field in Nashville, Tennessee.  (Photo by And
NASHVILLE, TN - JANUARY 10: Defensive tackle Albert Haynesworth #92 of the Tennessee Titans looks on after losing to the Baltimore Ravens 13-10 during the AFC Divisional Playoff Game on January 10, 2009 at LP Field in Nashville, Tennessee. (Photo by And

The Redskins did not learn their lesson with Dana Stubblefield. In 2008, Albert Haynesworth was the without question the best interior defensive lineman in the NFL. The Titans earned the top seed in the AFC and their defense allowed the second fewest points in the NFL.

Haynesworth was a main reason for their success and he finished third in the NFL Defensive Player of the Year voting. Considering how much attention he drew, his 8.5 sacks, 3 forced fumbles and 51 tackles (in just 14 games) were incredible numbers.

When the season was over, the Redskins lured him away from Tennessee with a seven-year, $100 million contract.  It has been a less than harmonious union in Washington.

No. 3: Adrian Beltre, 2004

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LOSANGELES - OCTOBER 10:  Third baseman Adrian Beltre #29 of the Los Angeles Dodgers takes a swing during the National League Division Series with the St. Louis Cardinals, Game Four on October 10, 2004 at Dodger Stadium in Los Angeles, California. The Car
LOSANGELES - OCTOBER 10: Third baseman Adrian Beltre #29 of the Los Angeles Dodgers takes a swing during the National League Division Series with the St. Louis Cardinals, Game Four on October 10, 2004 at Dodger Stadium in Los Angeles, California. The Car

After several disappointing seasons with the Los Angeles Dodgers, Beltre finally became one of the premier third basemen in baseball in 2004.

Not only did he break .300 for the first time in his career (his .334 average was fourth in the NL) and top 100 RBI for the first time ever, but he doubled his previous career best home run total. His 48 homers led the National League. The Dodgers also won the NL West for the first time in nearly a decade.

The Seattle Mariners gave the NL MVP runner-up a five-year, $64 million contract that winter. Naturally he never again hit .300, totaled 100 RBI or hit more than 26 home runs and the Mariners didn’t come close to contending for the AL West title.

No. 2: Barry Bonds, 1992

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SAN DIEGO - AUGUST 30: Barry Bonds #24  of the Pittsburgh Pirates watches the flight of his hit against the San Diego Padres on August 30, 1992 at Jack Murphy Stadium in San Diego, California. Barry Bonds made his 165 career home run during this game. Bar
SAN DIEGO - AUGUST 30: Barry Bonds #24 of the Pittsburgh Pirates watches the flight of his hit against the San Diego Padres on August 30, 1992 at Jack Murphy Stadium in San Diego, California. Barry Bonds made his 165 career home run during this game. Bar

Bonds already owned one NL MVP prior to last season with the Pirates. But just to solidify himself as the league’s premier position player, Bonds had the best season of his career (to that point, of course) in 1992.

He led the league in runs scored, totaled a career high in home runs and batting average and earned a third consecutive Gold Glove. He even (slightly) broke out of his infamous post-season slump in the 1992 NLCS as he grabbed six hits and a home run in Pittsburgh’s heartbreak loss to the Braves.

San Francisco was no doubt going to chase Bonds hard that off-season: the homecoming, along with his father, was probably too good to pass up.

But when Bonds earned his second MVP in three years following the 1992 season, Bonds was able to demand whatever he wanted from the Giants. And he did.

No. 1: Randy Moss, 2007

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EAST RUTHERFORD, NJ - DECEMBER 29:  Randy Moss  #81 of the New England Patriots celebrates his 22nd touchdown of the season tying the all-time season high for touchdowns in a season with teammate Russ Hochstein #71 against the New York Giants on December
EAST RUTHERFORD, NJ - DECEMBER 29: Randy Moss #81 of the New England Patriots celebrates his 22nd touchdown of the season tying the all-time season high for touchdowns in a season with teammate Russ Hochstein #71 against the New York Giants on December

Not only was Moss’ 2007 an incredible “contract year,” it was one of the finest individual seasons any wide receiver ever had.

After his lackluster career in Oakland, the Patriots traded for Moss prior to the 2007 season. And although he had two years left on his contract, Moss agreed to tear it up and sign a one-year deal with New England.

The Pats also covered their tracks: in case Moss was a problem, they weren’t wedded to him for long. Knowing that everyone would view him as a washout if he played as poorly in New England as he had with the Raiders, Moss rededicated himself in 2007. And the results were spectacular.

He caught 98 passed for 1,493 yards and set a new league record with 23 touchdown catches. By providing Tom Brady with a legitimate deep threat, the Patriots cruised to their famous 16-0 regular season.

Moss became a free agent after the All-Pro season but ultimately elected to return to the Patriots and has been one of the premier receivers since.  

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