Haves and have nots: Revisiting some of baseball's biggest contracts

On the heels of an 18-win season in San Diego and making a third consecutive All-Star team, the Los Angeles Dodgers inked Brown to an astonishing seven-year, $105 million deal. It made Brown baseball’s first $100 million man and sent shock waves through the industry. Entering his age 34 season at the time, Brown’s tenure in L.A. fell short regarding on-field success, as he averaged fewer than 10 wins per season as a Dodger. But it did reestablish the standard when it came to what a blockbuster free agent contract is.

Shortly after the Reds made the deal of the century at the time to bring over the game’s signature player from the Seattle Mariners, they inked him to a long-term extension. The nine-year, $113 million deal was the most lucrative in baseball at the time and took up 27 percent of the Cincinnati payroll. While Griffey would go on to have a few highlight moments as a member of the club — including his 500 ^th home run — a series of lower-body injuries severely clipped into his legendary production. Griffey never played more than 145 games in a season in Cincinnati and reached 40 home runs only once, after doing so in six of 11 seasons as a Mariner.

Although Rodriguez was easily baseball’s most anticipated free agent at the time, the fortune he would find on the open market stunned the nation. A-Rod received professional sports’ most lucrative contract of all time from the Texas Rangers when they signed him to a 10-year, $252 million deal. The contract was $63 million more than the next closest contract in the game. Rodriguez would win the AL MVP as a Ranger in 2003 and lead the American League in home runs in each year with the club, before being dealt to the New York Yankees prior to the 2004 season.

After refusing a seven-year, $119 million extension the previous year from the Cleveland Indians that would have made him the game’s highest-paid player, Ramirez tested his fortunes on the open market in a move that indeed paid off. While he would not claim the crown of owning the game’s top deal in the wake of A-Rod’s epic one, the eight-year, $160 million pact he inked with the Boston Red Sox was nothing to sneeze at. Ramirez would go on to be a centerpiece on the rebuilding of the Red Sox, culminating with their historic 2004 world championship team.

Of course not all huge deals are made in the open market, as some of the game's biggest deals have been made to keep a player from ever departing in the first place. A year after setting a record for most lucrative arbitration season in history, with a $10 million award for the 2000 season, Jeter became the second shortstop to shake up the 2001 offseason. His 10-year, $189 million deal became the third contract to top $150 million that offseason, the first time in MLB history this occurred. Of course, Jeter remained at the heart of the Yankee organization for rest of his career and helped bring the club its 27^th World Series championship during the contract.

One of the most surprising deals in baseball history, even at the time, was the $121 million deal the Colorado Rockies leveraged to lure Hampton to town. It was the biggest contract in baseball history, for a pitcher who had only once been an All-Star in his eight-year career. Hampton never became the salvation from the thin air that plagued all-comers to the Coors Field mound. He lasted only two seasons with the club, working to a 5.75 ERA and collecting 28 losses before being traded away to the Atlanta Braves.

In the winter of 2004, Guerrero departed from the relocating and rebranding Montreal Expos for the Anaheim Angels. Considering the massive deals that had preceded his, Guerrero’s could be a huge steal due to the production he continued to give. Guerrero received a five-year, $70 million deal and won AL MVP honors the following season. He was an All-Star in four of the five years of the deal, hit .319 in his Angels career and entered the Hall of Fame with the club’s logo on his cap.

After a historic showing with the Houston Astros, where he connected for a record-tying eight home runs and hit .435, Beltran hit the market red-hot. The Mets stepped up and gave him a seven-year, $119 million deal to come to Flushing, the 10 ^th deal in history to top $100 million. Injuries besieged the later portion of the deal, but Beltran’s New York tenure was a strong one overall, as he was a five-time All-Star, a three-time Gold Glove winner and hit 41 home runs in 2006 while taking the Mets to the NLCS.

The Giants spared no expense to lift the talented southpaw from their Bay Area rivals in Oakland, signing Zito to a seven-year, $126 million deal. It was the largest pitcher’s contract in MLB history. Unfortunately, Zito never came close to matching the pedigree he carried in Oakland, posting only one winning record during his time with the club, which didn’t come until 2012.

By 2007, Soriano had already been involved in one headline deal, as he was sent to the Rangers in exchange for Alex Rodriguez from the Yankees in 2003. Finally, Soriano’s day underneath the free agency lights had come around and he cashed in on an eight-year, $136 million deal with the Chicago Cubs, including a full no-trade clause. Soriano spent seven productive years with the Cubs; however the inability to move him in later years slowed the Cubs’ flexibility in being able to rebuild toward the end of the deal.

One of the biggest misses in big-contract history came via the Blue Jays' $126 million extension with Wells. Although at the time, Wells was a 27-year-old All-Star and Gold Glove recipient, it became a cautionary tale of the pitfalls of high-priced extensions. A string of injuries zapped his power numbers, which tumbled from a .499 pre-2007 slugging percentage, to .428 afterward — and during the heart of his biggest earning years. Wells ended up out of baseball at age 34 when the deal concluded, after hitting .226 over his final three years.

Rodriguez’s second high-profile foray into free agency featured more controversy than awe. After his intent to opt out of his current record-setting deal in pursuit of a second massive deal was announced during the final game of the World Series, Rodriguez drew the ire of many for an act deemed selfish. Eventually, Rodriguez negotiated directly with the Yankees on his own (without agent Scott Boras, who was preparing to pit the Boston Red Sox against the Yanks) and received a second record-setting deal, which totaled $275 million over 10 years.

The Yankees continued their big spending ways in an epic fashion in the winter of 2009. In an offseason where they spent over $400 million in an effort to reverse their recent struggles, Teixeira came away as the biggest winner of all. The first baseman received an eight-year, $180 million deal. The benefits came immediately, as the Yankees won the World Series the next fall, with Teixeira leading the AL in home runs (39), RBI (122) and total bases (344).

The second major coup of the Yankees' big winter of ’08 was Sabathia, who headed to the Bronx on the heels of a dominant 10-1 run with the Milwaukee Brewers. His eight-year, $161 million contract again re-established a high-water mark for pitcher deals. Sabathia would lead the AL in wins in both of his first two seasons and work to a 106-68 record during one of the best top-end pitching deals of recent history.

The Cardinals were badly in need of an impact bat to accompany Albert Pujols at the heart of their lineup in the summer of 2009 and needed just as badly to retain Holliday's services that winter. His seven-year, $120 million contract is the only pact in team history to exceed $100 million to date. Over the course of the deal, Holliday became a four-time All-Star and hit .293 with 156 home runs while helping the team to two World Series appearances (with a victory in 2011) — one with and one without Pujols.

While it wasn’t exactly a hometown discount, Mauer’s decision to stay home (literally) in Minnesota represented a strong show of loyalty by player and team alike. The eight-year, $184 million extension the two sides agreed upon in March of 2010 represented what equated to a lifetime contract. Nine years later it still stands as the richest contract ever for a catcher.

The Red Sox paid $142 million for Crawford in his speed-demon form of Tampa, but that version of him never showed up in Fenway. Injuries played a part, but underperformance did as well. Crawford spent just two of the seven years of his contract in Fenway before the Red Sox sent him as a part of a contract dump to the Los Angeles Dodgers alongside Adrian Gonzalez. He carried a .292 on-base percentage and stole only 23 bases over 161 games over two seasons.

Two years removed from winning NL MVP honors, the Reds awarded Votto handsomely with one of the largest true contract extensions in MLB history. With the two remaining years on the contract at the time, by the end of Votto’s 10-year extension he will have made $251.5 million on a contract that carries through 2024. So far in the life of the agreement, he has led the National League in on-base percentage in all but three years since.

It was not surprising what Pujols received in the winter of 2011, rather it was where it came from. The three-time NL MVP was synonymous with the St. Louis Cardinals, having just won a second World Series with the club. However, Arte Moreno’s Los Angeles Angels shockingly offered him a deal he could not refuse, in the form of a 10-year, $252 million contract to relocate to Anaheim. While Pujols has not been anywhere close to the same player in Anaheim as he was in St. Louis, it still stands as among the largest-ever free-agent deals in MLB history.

The Tigers had hopes of Fielder being the final piece to their puzzle, alongside Miguel Cabrera, when they inked him to a nine-year, $214 million deal in January of 2012. While he would be traded to the Texas Rangers two years later, his career would never see the duration of the contract. A severe neck injury forced him into retirement just four years into the pact, with $48 million still due before a 2018 escape clause.

King Felix was already sitting high on his throne in Seattle — owner of a Cy Young Award in 2010 and author of a perfect game the year before. By the spring of 2013, Hernandez also became (albeit briefly) the highest-paid pitcher in baseball history when the Mariners gave him a seven-year, $175 million deal that carries through 2020. Hernandez initially lived up to the billing, although he is just 15-27 with a 5.43 ERA since 2017.

On the heels of Hernandez’s historic extension in February, the Tigers did Verlander $7 million better the following month. Thus far the seven-year, $180 million extension that includes a $22 million vesting option in 2020 for Verlander has been a vastly better investment. While JV has had his ups and downs over the five-year run, he has recently returned to his top-tier form, picking up ALCS MVP honors after being traded to the Houston Astros in 2017 and finishing in the top five of AL Cy Young voting for three years until winning it this past season for the second time in his career.

After winning a pair of World Series, Rookie of the Year, a batting title and NL MVP in his first three seasons, the Giants felt the coast was clear to fully commit to Posey on a long-term basis. They did that via an eight-year, $167 million extension in the spring of 2013, the second-largest deal ever for a catcher. Posey continues to deliver on the promise, having won a third World Series in 2014 and making the NL All-Star team in five of the seven years under the deal so far.

While it might have not been a necessary move at the time, one of the final decisions of the bizarre tenure of Jeffrey Loria’s reign over the Marlins changed the contractual landscape of the game permanently. The notoriously frugal owner gifted Stanton a record 13-year, $325 million extension that included a full no-trade clause. The future NL MVP would eventually negotiate a trade to the New York Yankees as a part of the ongoing gutting of the Marlins organization — which was mainly necessitated by the crippling terms of Stanton’s contract that will earn him a peak of $32 million per year.

Kershaw entered the 2014 season not only with his second NL Cy Young win in the past three years but also with a handsome new contract in tow for his troubles. The seven-year, $215 million deal bested Justin Verlander’s previous pitching-high contract by $25 million and made Kershaw the first player to ever earn $30 million in one season. Overall, Kershaw currently has three highest-earning seasons in MLB history, averaging $35.1 million from 2016 through 2018. The Dodgers tacked on another three years and $93 million before last season.

Cano stunned the industry when he turned down a $175 million deal to stay with the Yankees. However, it turned out to be a show of good foresight, as the Mariners took a 10-year, $240 million offer to the table to make Cano the centerpiece of the club’s rebuilding efforts. While Cano has made three All-Star Games as a Mariner, the club has failed to make the playoffs yet with him. An 80-game PED suspension in 2018 provided a sizable stain on his reputation as well.

After receiving an eight-year, $152 million extension in 2008 (which was the fourth-largest in MLB history at the time) shortly after arriving in Detroit, Cabrera again cashed in headed into the 2014 season. On the heels of two consecutive MVP wins coupled with completing the first Triple Crown in 45 years, the Tigers inked a likely lifetime pact with Cabrera in the form of an eight-year, $248 million extension. Cabrera responded by winning a fourth batting title in 2015, although back troubles have limited him since.

A strong case can be made for Scherzer being the greatest free agent pitching addition of all-time. Since joining the Nationals in January of 2015, Scherzer has twice won NL Cy Young Award honors, twice led the circuit in wins and led the league in strikeouts and WHIP three years running and helped guide his team to a World Series crown. The financially savvy hurler will see the final payout of the seven-year, $210 million deal in 2035, as his $50 million signing bonus will payout an additional 14 years on the back end of the contract, the longest deferral in MLB history.

The career of Trout has been defined by rewriting expectations on the fly, so it should come as no surprise that he did so at the bank as well. Trout made history when he signed a six-year, $144.5 million deal in March of 2014, which blew away the previous record for a pre-arbitration extension. By 2018, the deal escalated to Trout making $34 million per year, the most in history by a positional player in a single season. Before the 2019 season, Trout inked a $430 million deal over 12 years — the richest ever in sports — and then went on to win the AL MVP for the third time in his career.

The bar was raised again for a pitching deal, when Price signed with the Red Sox for $217 million over seven years, just $2 million more than Clayton Kershaw’s previous record amount. The $31 million annual value tied with Cabrera for the most in MLB history. After a rocky first two years in Boston marred with injuries and playoff failures, Price broke through in 2018, pitching in both of the decisive ALCS and World Series games for the Red Sox.

Greinke has established himself as the most fearless negotiator in the game. After going 19-3 and leading the NL with a 1.66 ERA in 2015, Greinke opted out of the remaining $77 million on his deal with the Dodgers in favor of a record-setting, six-year, $206 million deal with the Arizona Diamondbacks. At the time, the new contract made him the highest-paid player in baseball on annual basis, earning no less than $34 million per year during the deal through his age 37 season. Greinke has made the All-Star team in each of the previous three seasons. He went 8-1 after being traded to Houston last season.

Throughout the summer of 2016, the pending free agency of Stephen Strasburg was a much talked about forthcoming event — until it wasn’t. The talented righty suddenly signed a seven-year, $175 million dollar extension with the Nationals, seemingly going against the established logic of the industry and especially against the norm of Scott Boras' clients. However, the contract included a pair of never-before-seen escape clause options after both the 2019 and 2020 seasons, allowing Strasburg the unusual ability to navigate his own future, which he did. Now a free agent, it remains to be seen what kind of contract a team is willing to give him after being named the MVP of the World Series.

In December of 2015, Heyward signed a $184 million contract that stretched over eight years, the largest by an outfielder on the open market in MLB history. While there certainly had been contracts of this magnitude before, the unique part of Heyward’s decision was the amount of repeat control he held within its structure. He received two player opt-out clauses over the life of the deal: one after the third year in 2018 and another two years later. This type of extended conditional freedom could set the bar for how many future long-term deals are constructed.

With rumors of his potential contract reaching as high as $400 million and every major market team in the game being associated with him, the possibilities seemed endless for Harper ahead of the 2019 season. Ultimately, it was his former divisional rivals, the Philadelphia Phillies, who emerged victorious in acquiring him, via a 13-year, $330 million contract that is currently the largest free agent contract in MLB history and second-largest overall. The iron-clad deal also gave Harper full no-trade rights and no opt-outs, meaning that Harper is in for the long haul with the Phils.

Alongside Harper, Machado’s foray into free agency was half of the most hyped open market trip of all-time. Unlike Harper, Machado’s market was truly completely open for business, as there was little to no chance of him returning to the Los Angeles Dodgers. After the Chicago White Sox made a serious push to land the services of the five-tool infielder, it was the small market San Diego Padres who swooped in and added Manny as their franchise player, giving him a stunning 10-year, $300 million dollar deal.