Big-Money MLB Contracts That Were Worth Every Penny

When an elite MLB player is due a new contract, the inherent risk for teams is that the future salaries will outweigh his production.

But those pricey contracts can also pay enormous dividends.

Plenty of current big-money deals will probably be remembered favorably, too. As much as we might believe in a certain player, though, performance over the lifetime of a contract is a key factor here.

Additionally, the minimum salary total is $100 million. Not every successful deal is mentioned; rather, the focus is on contracts that most benefited both the player and team.

The choices are subjective but based on a blend of individual production and team success.

Contract: Eight years, $160 million

Manny Ramirez played eight seasons in Cleveland before heading to the Boston Red Sox in 2001.

All he did was become a franchise legend.

Ramirez played an integral role in the Sox breaking the legendary curse and winning the World Series in 2004. However, he truly played well throughout the entirety of his contract.

Over the life of his eight-year deal, Ramirez hit .316 with a .415 on-base percentage. He averaged 34 doubles, 36 home runs and 115 runs batted in, along with 84 walks to 111 strikeouts. He led the American League in batting average and slugging once and OBP three times, making eight All-Star appearances and winning six Silver Sluggers.

Most memorably, of course, Ramirez earned World Series MVP after hitting .412 in the triumph over the St. Louis Cardinals.

Contract: 10 years, $252 million

For you, the cloud of performance-enhancing drugs may cloud the legacy of Alex Rodriguez. But, honestly, I'm not concerned about it. He still had to actually hit the ball.

After breaking into the majors with the Seattle Mariners, he inked a 10-year, $252 million pact with the Texas Rangers in 2001.

Rodriguez paced the American League in home runs during each of his three seasons with Texas, totaling 156 while adding 100 more extra-base hits and 395 RBIs. He won three Silver Sluggers, two Gold Gloves and the 2003 AL MVP.

Texas sent A-Rod to the New York Yankees in a 2004 blockbuster trade, and he continued to excel. Through the 2010 season, he hit .296 with a .393 OBP and notched 27 doubles, 38 homers and 120 RBI per year. Rodriguez padded his trophy case with two more AL MVPs, three Silver Sluggers and six All-Star nods.

Rodriguez also won his lone championship in 2009, finishing with the Yankees' second-most RBIs (six) in the series.

Contract: Eight years, $116 million

Following a blistering three-year stretch to open his MLB career—complete with top-four finishes in NL MVP voting each season—Albert Pujols secured his mega-contract in 2004.

It might be the greatest nine-figure deal in league history.

Pujols sparked a tremendous run for the Cardinals, who reached the World Series three times and earned two rings during this contract. They also won four NL Central titles.

Meanwhile, the future Hall of Famer posted a .326/.424/.618 slash line with averages of 40 doubles, 41 homers, 118 RBIs and 94 walks to 60 strikeouts. He stockpiled three MVPs—with two more runner-up finishes—four Silver Sluggers and two Gold Gloves along the way.

Pujols then signed a well-deserved 10-year, $240 million agreement with the Los Angeles Angels. That one aged poorly, but he'd been an absolute bargain in St. Louis for 11 years.

Contract: Eight years, $152.3 million

At the end of the 2023 season, Miguel Cabrera wrapped up a rough eight-year, $248 million pact.

Consider it proper payment for the absolute steal of his prior deal.

Acquired from the Florida Marlins in a December 2007 trade, Cabrera promptly signed an eight-year extension that doubled as the largest contract in Detroit Tigers' history. Also, the smartest.

Cabrera registered an absurd .326/.406/.574 slash line across eight seasons, averaging 39 doubles, 34 homers and 114 RBI. He paced the AL in doubles, homers and slugging percentage twice and both batting average and on-base percentage four times.

Most memorably, he secured the Triple Crown—the first in 45 years—in 2012, the first of back-to-back MVP campaigns.

Detroit didn't win a ring but reached the World Series in 2012 and won four consecutive AL Central titles from 2011-14.

Contract: Eight years, $135 million

Shortly before the 2014 season, Freddie Freeman agreed to the largest contract in franchise history. What makes the extension most remarkable, though, is what happened during its term.

In the mid-2010s, the Braves found themselves in the awkward position of transitioning from a memorable era to a revamped team while remaining competitive. They sort of did, but quickly lost in the postseason. Soon enough, the front office began tearing down the roster.

Freeman stayed, however, and Atlanta built around him. Good choice.

As the Braves ascended in 2018, so did Freeman. The sweet-fielding first baseman cracked an NL-high 191 hits and won a Gold Glove that season. Then, he blasted a career-best 38 homers and won a Silver Slugger in 2019. Freeman won the NL MVP in the shortened 2020 season and scored an NL-leading 120 runs during the following year.

Freeman capped the contract with a World Series win in 2021 before continuing his career with the Los Angeles Dodgers.

Contract: Five years, $150 million

Technically speaking, Clayton Kershaw inked a seven-year contract worth $215 million in 2014. However, he exercised an opt-out option after the 2018 season to re-sign a new deal with the Dodgers.

No matter the actual money—in this case, $150 million—the southpaw lived up to the expectations.

Already a two-time NL Cy Young winner, Kershaw took home a third in 2014. He recorded a 76-23 mark and stunning 2.12 ERA during those five seasons. Also, in 2015, Kershaw became the first pitcher in more than a decade to amass 300 strikeouts in a year.

Los Angeles couldn't yet crack the World Series barrier—the elusive ring finally arrived in 2020—but Kershaw helped guide the Dodgers to five straight NL West titles.

Contract: Seven years, $210 million

Max Scherzer took a superstar turn with the Tigers in 2013, winning 21 games and an AL Cy Young. He posted an AL-high 18 victories in 2014 on his way into the free-agent market.

Simultaneously, the Washington Nationals became a contender. They reached the playoffs in 2012—the first postseason bid since leaving Montreal in 2005—notched 86 wins in 2013 and grabbed a second NL East crown in 2014. It was time to embrace a championship chase.

Enter: Scherzer.

Over the next five seasons, he posted a 79-39 record with a 2.74 ERA, received two NL Cy Youngs and propelled the Nats to three playoff berths. They won a World Series in 2019 as Scherzer registered a 3-0 mark and 2.40 ERA over 30 postseason innings.

Scherzer pitched well through the 2021 season, although Washington entered a rebuild after sending him and shortstop Trea Turner to the Dodgers in a deadline trade.

Contract: Seven years, $180 million

Oh, no big deal, Justin Verlander only signed the largest contract for a pitcher in MLB history at the time.

Now that's some risk.

Early on, Detroit probably had concerns about the deal. Verlander managed a 33-32 record with a 3.84 ERA through three seasons. But he tallied an AL-best 254 strikeouts in 2016, a campaign that sparked an incredible late-career breakout for the 2011 Cy Young winner.

After the Tigers sent JV to the Houston Astros in a 2017 trade, he went 9-1 and yielded only 13 runs in 70.2 innings across 11 appearances. Houston—while controversial in hindsight—won its first-ever World Series.

In the next two seasons, Verlander boasted a 37-15 record with a 2.55 ERA. He paced the AL in strikeouts (290) and finished second in Cy Young voting in 2018 and improved to 300 with the prestigious honor in 2019.

As if that's not enough, he overcame Tommy John surgery to win a third Cy Young in 2022 on a later contract.