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JUPITER, FL - FEBRUARY 17: Albert Pujols # 5 of the St. Louis Cardinals warms up prior to infield practice at Roger Dean Stadium on February 17, 2011 in Jupiter, Florida. (Photo by Joel Auerbach/Getty Images)
JUPITER, FL - FEBRUARY 17: Albert Pujols # 5 of the St. Louis Cardinals warms up prior to infield practice at Roger Dean Stadium on February 17, 2011 in Jupiter, Florida. (Photo by Joel Auerbach/Getty Images)Joel Auerbach/Getty Images

MLB Predictions: Baseball's Next 10 $100 Million Contracts

Peter WardellJun 7, 2018

There are two main ways that a player reaches the $100 million clip on a contract:

The first, and most common way, is through free agency. At this point, most players are aged 29-31, hitting or pitching at the top of the league and clearly in their career years. A big team with lots of money (Boston Red Sox, New York Yankees) or a team hoping to make a huge splash (Washington Nationals, Chicago Cubs, San Francisco Giants) comes along and tries to lock up the player to a six- to eight-year deal.

The second way that has caught on recently is through contract extensions. This is the common method of the smaller and mid-market teams to keep a top player around before they file for free agency. This is a common tactic employed by many teams to lock up a player around age 25-26 through their peak years, ending when they’re around 32-33. Some examples include Albert Pujols (2004), Miguel Cabrera (2008) and Troy Tulowitzki (2011). 

Here’s a look at the next $100 million contracts to be signed. 

Albert Pujols

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JUPITER, FL - FEBRUARY 28: Albert Pujols #5 of the St. Louis Cardinals plays the field against the Florida Marlins at Roger Dean Stadium on February 28, 2011 in Jupiter, Florida.  (Photo by Marc Serota/Getty Images)
JUPITER, FL - FEBRUARY 28: Albert Pujols #5 of the St. Louis Cardinals plays the field against the Florida Marlins at Roger Dean Stadium on February 28, 2011 in Jupiter, Florida. (Photo by Marc Serota/Getty Images)

Albert Pujols will break the record for largest contract in the history of baseball next offseason. Currently, the St. Louis Cardinals slugger is starting discussions with 10 years for $300 million. He is the best player in the game, and someone will pay.

Pujols has unanimously been the top slugger in the game for the last five years. Only three times in the history of baseball has a player signed a $100M deal prior to turning 27—Pujols did at 24. It’s no doubt that both the Cardinals (and the rest of the league, for that matter) realize that Pujols is a once-in-a-generation talent. He has become the face of the St. Louis franchise and a reason for fans to come out to Busch Stadium.

Surprisingly, the Cardinals and Pujols’ camp were unable to reach an agreement this offseason. It is unclear at the moment whether the two will reconvene as the season comes to an end in an attempt to hash out a deal, or whether Pujols will test the free-agent market. For one season, $30M can buy three or four everyday ballplayers, two low-end All-Stars or one elite superstar. It is now a matter of what St. Louis wants to do.

When To Expect It: prior to the 2011 Winter Meetings 

With Whom: St. Louis (re-sign) or Chicago Cubs

Similar Contract: Alex Rodriguez’s 10 year/$275M

Prince Fielder

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PHOENIX, AZ - MARCH 10:  Prince Fielder#28 of the Milwaukee Brewers swings the bat against the Colorado Rockies during the spring training baseball game at Maryvale Baseball Park on March 10, 2011 in Phoenix, Arizona.  (Photo by Kevork Djansezian/Getty Im
PHOENIX, AZ - MARCH 10: Prince Fielder#28 of the Milwaukee Brewers swings the bat against the Colorado Rockies during the spring training baseball game at Maryvale Baseball Park on March 10, 2011 in Phoenix, Arizona. (Photo by Kevork Djansezian/Getty Im

Next to Albert Pujols, Milwaukee Brewers first baseman Prince Fielder will sign the the largest contract next season. And it could be the third-largest contract amount of all-time (behind Pujols’ looming deal and A-Rod’s $275M).

First baseman power hitters have a very strong history of cashing in huge during free agency. Fielder, who will be just 27 years old at season’s end, has already become one of the game’s most feared power hitters and a steady threat for the home run crown from season to season. Bidding looks to be high, as first basemen seem to always be in demand. Fielder makes for a great cleanup bat and he is just now entering the typical peak years of his career.  

Although the Brewers would love to retain Fielder, the team’s first-round pick (seventh overall) in the 2002 amateur draft, Milwaukee cannot afford the amounts that “franchise players” have been receiving over the last couple seasons. 

When To Expect It: Prior to the 2011 Winter Meetings

With Whom: The highest bidder (Chicago Cubs? Toronto?)

Similar Contract: Mark Teixeira’s eight-year/$180M

Adrian Gonzalez

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FORT MYERS, FL - MARCH 14:  Infielder Adrian Gonzalez #28 of the Boston Red Sox bats against the New York Yankees during a Grapefruit League Spring Training Game at City of Palms Park on March 14, 2011 in Fort Myers, Florida.  (Photo by J. Meric/Getty Ima
FORT MYERS, FL - MARCH 14: Infielder Adrian Gonzalez #28 of the Boston Red Sox bats against the New York Yankees during a Grapefruit League Spring Training Game at City of Palms Park on March 14, 2011 in Fort Myers, Florida. (Photo by J. Meric/Getty Ima

Boston Red Sox first baseman Adrian Gonzalez should be the first of this list to enter the $100 million-plus contract club. The underwriting for a seven-year, $164M deal is in the works, but has not been signed. Gonzalez’s agent, John Boggs, will be visiting the team in Florida next week, and talks between the two parties could resume.

The 28-year-old Gonzalez is one of the premier first basemen in the game and entering the prime of his career. This offseason, Boston traded a package of prospects to San Diego for Gonzalez, with preliminary agreements that he would sign long-term with Boston.

At the moment, it is not clear whether the two sides are still debating contract deals or whether Boston is holding off to announce the deal in order to avoid additional luxury-tax penalties. Regardless, Gonzalez will be locked up in the very near future and will be a mainstay at first base for Boston for a very long time.

When To Expect It: Opening Day 2011

With Whom: Boston

Similar Contract: Mark Teixeira’s eight-year/$180M (prorated to one less year)

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Jose Reyes

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PORT ST. LUCIE, FL - FEBRUARY 26: Jose Reyes #7   of the New York Mets strikes out against the Atlanta Braves at Digital Domain Park on February 26, 2011 in Port St. Lucie, Florida.  (Photo by Marc Serota/Getty Images)
PORT ST. LUCIE, FL - FEBRUARY 26: Jose Reyes #7 of the New York Mets strikes out against the Atlanta Braves at Digital Domain Park on February 26, 2011 in Port St. Lucie, Florida. (Photo by Marc Serota/Getty Images)

New York Mets shortstop Jose Reyes is clearly playing for a contract this season. After back-to-back injury-plagued seasons, for Reyes to land a long-term contract, he needs to prove that he can go 155-plus games and not be an injury liability in the future. It is a good thing that he has reported that he feels 100 percent and like he has something to prove this season.

Reyes is one of baseball’s most dynamic players, contributing at the plate, in the field and most notably on the base paths. At full health, he is an MVP candidate, but Mets GM Sandy Alderson, amid all the financial issues in New York, has said he will wait until he sees results from the 27-year-old before offering a long-term deal. Along side David Wright, Reyes has become a face of the franchise and both management and Mets fans hope to see him return to form in 2011.

Reyes, who will be 28 this June, is entering the typical peak years of a player’s career. His athletic frame and ability should allow him to remain an impact player in the league for the next decade.

When To Expect It: Prior to the 2011 Winter Meetings

With whom: New York Mets

Similar Contract: Carl Crawford’s seven-year/$142MM

Zack Greinke

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PHOENIX, AZ - MARCH 10:  Pitchers Zack Greinke #13 and Shaun Marcum #18  of the Milwaukee Brewers look at fans during the spring teaining baseball agme against Colorado Rockies at Maryvale Baseball Park on March 10, 2011 in Phoenix, Arizona.  (Photo by Ke
PHOENIX, AZ - MARCH 10: Pitchers Zack Greinke #13 and Shaun Marcum #18 of the Milwaukee Brewers look at fans during the spring teaining baseball agme against Colorado Rockies at Maryvale Baseball Park on March 10, 2011 in Phoenix, Arizona. (Photo by Ke

For seven straight seasons, Zack Greinke led a sub-.500 team that was in “rebuilding mode” and showed no signs of sniffing the postseason. In five of those seasons, the Royals lost 90-plus games. For the 27-year-old Greinke, who is already viewed as one of the top pitchers in the game, it is not about money, but about having the opportunity to pitch for a playoff contender.

Greinke has two years left on his contract, now with the Milwaukee Brewers, and is slated to be a free agent following the 2012 campaign. Before allowing a trade to Milwaukee over the offseason, Washington offered Kansas City a deal including a $100M extension for Greinke. With Washington’s competitive clock unexpected until 2012-2013, Greinke declined. Come two years from now, Greinke should receive similar offers, as he will be just 29 and in the prime years of his career.

The thing about Greinke is that based on his psychological history, he seems unsuited to play somewhere like the Big Apple or Boston, the two largest media markets in baseball with the two largest checkbooks. Greinke is talented enough, however, and young enough that he should earn some large, long-term offers from playoff-contending, mid-market teams.

When To Expect It: 2012 Winter Meetings

With Whom: Mid-market, contending team (i.e. Washington, St. Louis, Atlanta)

Similar Contract: Cliff Lee’s five-year/$120M (but less money)

Andre Ethier

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PHOENIX, AZ - FEBRUARY 27:  Andre Ethier #16 of the Los Angeles Dodgers at bat during spring training at Camelback Ranch on February 27, 2011 in Phoenix, Arizona.  (Photo by Harry How/Getty Images)
PHOENIX, AZ - FEBRUARY 27: Andre Ethier #16 of the Los Angeles Dodgers at bat during spring training at Camelback Ranch on February 27, 2011 in Phoenix, Arizona. (Photo by Harry How/Getty Images)

During this past offseason we saw a solid, power-hitting corner outfielder (Jayson Werth) turn three years of elite production into a seven-year, $126M deal with a team on the rise that was looking for a big bat (Washington Nationals).

Over the last two (possibly even three) seasons, Los Angeles Dodgers outfielder Andre Ethier has been elite and, at times, MVP-caliber. In fact, Werth’s and Ethier’s numbers line up pretty similarly. Under team control for two more seasons, Ethier could be in line for a huge payout during free agency after the 2012 season, when he will be 29 years old.

Ethier has easily been the Dodgers’ best and most consistent offensive source of the past couple seasons, but the owners’ financial issues and the Dodgers’ unwillingness to sign any of their young stars to long-term deals means Ethier could be gone in just two seasons.

Ethier is arbitration-eligible for the last time after the 2011 season and could see a nice salary boost from $9.25M he makes this year. The Dodgers could strike a multi-year deal with Ethier prior to arbitration hearings next winter or they could choose to go with a one-year deal, allowing him to walk at the end of the season.

Should he walk, Ethier will definitely earn interest around the league from both big markets trying to land a consistent middle-of-the-lineup hitter and the prospect-laden teams looking for a big bat to build around for the future. Ethier could easily fit in either plan.

When To Expect It: 2012 Winter Meetings

With Whom: Anyone

Similar Contract: Jayson Werth’s seven-year/$126MM

Ubaldo Jimenez

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ST. LOUIS - OCTOBER 2: Starter Ubaldo Jimenez #38 of the Colorado Rockies pitches against the St. Louis Cardinals at Busch Stadium on October 2, 2010 in St. Louis, Missouri.  The Cardinals beat the Rockies 1-0 in 11 innings.  (Photo by Dilip Vishwanat/Get
ST. LOUIS - OCTOBER 2: Starter Ubaldo Jimenez #38 of the Colorado Rockies pitches against the St. Louis Cardinals at Busch Stadium on October 2, 2010 in St. Louis, Missouri. The Cardinals beat the Rockies 1-0 in 11 innings. (Photo by Dilip Vishwanat/Get

As mentioned in the introduction, large, six- to seven-year contract extensions have become popular among teams, most recently handed out by the Colorado Rockies, who locked up seven-year extensions with both Troy Tulowitzki and Carlos Gonzalez this winter. Despite all of the guaranteed money going to the Rockies’ new young offensive studs, general manager Dan O’Dowd has said the 2010 breakout ace, Ubaldo Jimenez, will be discussed for a long-term contract extension as well in the near future.

Last season, Jimenez put together one of the best statistical first halves of all-time, posting a 2.20 ERA and 1.05 WHIP while going 15-1. He is recognized as one of the National League’s best pitchers and a face of the Colorado franchise along side CarGo and Tulo.

While Jimenez is under team control through the end of 2014 contractually, he could be in talks within the next season or two for a sizable five- to six-year extension. For the past three seasons, he has been in the top 10 for games started and looks to be an elite, durable starter for quite some time.

When To Expect It: 2012 offseason (before 2012 season)

With Whom: Colorado

Similar Contract: Barry Zito’s seven-year/$126M

Joey Votto

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SCOTTSDALE, AZ - MARCH 14:  Joey Votto #19 of the Cincinnati Reds against the Colorodo Rockies during the spring training baseball game at Salt River Fields at Talking Stick on March 14, 2011 in Scottsdale, Arizona.  (Photo by Kevork Djansezian/Getty Imag
SCOTTSDALE, AZ - MARCH 14: Joey Votto #19 of the Cincinnati Reds against the Colorodo Rockies during the spring training baseball game at Salt River Fields at Talking Stick on March 14, 2011 in Scottsdale, Arizona. (Photo by Kevork Djansezian/Getty Imag

Last year’s National League MVP, Joey Votto, recently signed a three-year, $38M deal with the Cincinnati Reds that will take him through the 2013 MLB season. For the Reds, it keeps the team from having to go through arbitration with their lefty slugger, while from Votto’s standpoint, it does not affect his first season of free-agent eligibility.

However, the fact of the matter is, with the way Votto crushed the ball in 2010 with a .324 batting average with 37 home runs, he could be looking at a sizable long-term extension in the near future. At the moment, the Reds are still holding out for 23-year-old outfielder Jay Bruce to pan out and become the centerpiece for the team, but if Votto posts another great campaign in 2011, the Reds will be forced to act before Votto can sniff free agency.

Votto’s three-year contract is back-heavy (’11: $5.5M, ’12: $9.5M, ’13: $17M), meaning it sets up very well for a four- to six-season extension. Just 27 years old, Votto looks to be a durable player and should continue to develop over the upcoming seasons. 

When To Expect It: 2013 offseason (before 2013 season)

With Whom: Cincinnati

Similar Contract: Ryan Howard’s five-year/$125M

Josh Hamilton

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SURPRISE, AZ - MARCH 02:  Josh Hamilton #32 of the Texas Rangers runs to first base during the spring training game against the Los Angeles Angels of Anaheim at Surprise Stadium on March 2, 2011 in Surprise, Arizona.  (Photo by Christian Petersen/Getty Im
SURPRISE, AZ - MARCH 02: Josh Hamilton #32 of the Texas Rangers runs to first base during the spring training game against the Los Angeles Angels of Anaheim at Surprise Stadium on March 2, 2011 in Surprise, Arizona. (Photo by Christian Petersen/Getty Im

This February, 2010 American League MVP Josh Hamilton signed a two-year, $24M contract, avoiding his final two seasons of arbitration and taking him up to his first year of free agency eligibility at the end of the 2012 season. It is unclear whether Hamilton will be stuck with quite a few short-term deals throughout his career or whether he will be offered a long-term extension in the near future.

At the end of the 2012 season, Hamilton will be 31 years old, a time considered the tail end of a player's prime. Hamilton has five-tool ability but with his major league career failing to start until age 26 due to a history everyone is aware of by now, many teams—the Rangers included—pause at a long-term deal. If he continues to produce at an MVP-caliber level in 2010 however, the Rangers will certainly lock him up.

Hamilton’s two-year deal breaks down to $7.25M in 2011 and $13.75M in 2012, values that could go up even more with two more elite campaigns. While some teams balk at Hamilton’s age, Jayson Werth was 31 this offseason when he signed his lucrative contract with the Nationals. The added mystery to Hamilton would likely bring about a shorter deal however.

When To Expect It: 2012 season

With Whom: Texas

Similar Contract: Carlos Lee’s six-year/$100M (with a little more money)

Francisco Liriano

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FORT MYERS, FL - FEBRUARY 23:  Pitcher Francisco Liriano #47 of the Minnesota Twins throws during a spring training workout session at Hammond Stadium on February 23, 2011 in Fort Myers, Florida.  (Photo by J. Meric/Getty Images)
FORT MYERS, FL - FEBRUARY 23: Pitcher Francisco Liriano #47 of the Minnesota Twins throws during a spring training workout session at Hammond Stadium on February 23, 2011 in Fort Myers, Florida. (Photo by J. Meric/Getty Images)

In the past decade, long-term pitching contracts haven't had the best track record. Johan Santana (2008), Barry Zito (2007) and Mike Hampton (2001) were all at the top of their position when they signed their lucrative deals and failed to perform.

While many teams are beginning to shy away from the long-term deal for starters, there are still some that will take the risk. The next young pitcher that will be in talks for a long-term, nine-figure deal is Minnesota Twins ace Francisco Liriano.

After a dominant 2010 campaign, the Twins and Liriano settled on a $4.3M pre-arbitration contract. Another injury-free, stellar campaign would mean a significant boost for the 2012 season, his last one under Twins team control.

In going season-to-season on the contract, it appears one of two things may be happening in Minnesota: 1) the Twins are not willing to invest in a pitcher who underwent Tommy John surgery just two seasons ago, or 2) Liriano is looking for big bucks in a contract extension that Minnesota can’t afford in a mid-level media market.

Without a doubt, the 27-year-old Liriano has one of the highest ceilings in all of baseball. He has the makings of a dominant, Cy Young-contending ace and would be a tremendous get for any team.

One team that has been in trade talks with the Twins this March has been the New York Yankees. After Cashman dangled a six-year, $140M deal last winter to 32-year-old Cliff Lee, it is certainly a possibility that Liriano could be offered a similar package or extension if the Yankees trade for him.

When To Expect It: 2013 offseason (after the 2012 Winter Meetings)

With Whom: New York Yankees/Boston (major market)

Similar Contract: Cliff Lee’s five-year/$120M

Notes

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NEW YORK - JULY 2: (L-R) Alex Rodriguez #13, Derek Jeter #2, Francisco Cervelli #29, pitching coach Dave Eiland #58, CC Sabathia #55 and Robinson Cano #24 of the New York Yankees meet on the mound during action against the Seattle Mariners at Yankee Stadi
NEW YORK - JULY 2: (L-R) Alex Rodriguez #13, Derek Jeter #2, Francisco Cervelli #29, pitching coach Dave Eiland #58, CC Sabathia #55 and Robinson Cano #24 of the New York Yankees meet on the mound during action against the Seattle Mariners at Yankee Stadi

Robinson Cano’s contract ends at the end of the 2011; however the Yankees have club options on him for the 2012 and 2013 seasons. Both salaries would be bargains for his value so we will likely not see nine-digit figure contract talks for a few more years.

CC Sabathia has the option to opt out of his contract after the 2011 season. He is slated to make $97M over his final four seasons under contract with the Yankees and could very well opt out to up his sum above $100M.

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