The 2019 Winter Meetings were host to two record-setting deals for pitchers, not to mention another in the top 10 of free-agent contracts by total value.
On Monday, Stephen Strasburg re-signed with the Nationals for $245 million, setting a record for a pitcher’s contract by both total value and average annual value.
On Tuesday night, news broke that Gerrit Cole signed, and Strasburg’s records were already history. Cole’s reported $324 million deal set a record for average annual value for any player regardless of position, at $36 million, and became the largest total value for a pitcher.
On Wednesday night, it was reported that Anthony Rendon signed a seven-year, $245 million deal with the Angels, a mirror image of his former teammate Strasburg’s deal.
Bryce Harper still tops the list of the largest contracts in Major League history, but Cole isn't far behind. Here are the 10 biggest contracts MLB free agents have ever received. (Note: These don't include contract extensions where the player didn't actually become a free agent, like the 12-year, $426.5 million extension Mike Trout signed with the Angels on March 20, 2019.)
1) Bryce Harper, Phillies: 13 years, $330 million (2019-31)
Harper's impending free agency defined his final season with the Nationals and dominated headlines all the way into the second week of Spring Training games, and a number of factors collaborated along the way to get Bryce to the top of this list. First was Stanton's record extension with the Marlins in 2014, which gave Harper and his agent Scott Boras an early goal for the most guaranteed money of any kind for an MLB player. Then, Machado inked his $300 million deal with the Padres in mid-February, giving Harper a floor for the contract he could demand from his final suitors that reportedly included the Phillies, Giants and Dodgers. Multiple reports stated that San Francisco lengthened its offer from a short-term structure to a much longer commitment in the final days leading up to Harper's signing, so Philadelphia's 13-year commitment might have put the NL East club over the top.
Harper's deal -- the biggest free-agent contract in the history of the four major North American professional sports -- includes a full no-trade clause, per multiple reports, but notably does not include any opt-outs, making it a straightforward, old-school mega-contract. Harper and the Phillies are committed to each other for more than a decade to come.
2) Gerrit Cole, Yankees: 9 years, $324 million (2020-28)
With Cole’s deal setting a record for pitchers, both of the top two free-agent deals by total value were given to No. 1 overall picks. Cole was taken first overall by the Pirates in 2011, while Harper was first overall in ‘10. Cole’s nine years are also the second most for any pitcher contract, trailing only Wayne Garland’s 10-year contract in the 1970s, in a far different era of free agency.
Cole, considered perhaps the best active pitcher, will bring strikeouts upon strikeouts to the Bronx. He had 21 10-strikeout games in 2019, while all Yankees pitchers combined for seven such games. The single-season franchise record for an individual is nine games, by David Cone in 1998.
3) Manny Machado, Padres: 10 years, $300 million (2019-28)
Though he ultimately won't bring a record deal into 2019, Machado does hold the distinction as being the first $300 million free agent in MLB history with the deal he inked with San Diego. An elite two-way player, Machado will anchor what the Padres hope will be a bright future, with shortstop phenom Fernando Tatis Jr. playing next to him, and many more elite up-and-comers on the way from MLB's top farm system.
4) Alex Rodriguez, Yankees: 10 years, $275 million (2008-17)
In the middle of Game 4 of the 2007 World Series, Rodriguez's agent, Scott Boras, announced that A-Rod would be opting out of the final three years of his contract with the Yankees. (This was the contract he had originally signed with the Rangers prior to the '01 season, which carried over to New York when he was traded in '04.) The timing created a torrent of controversy, and it seemed like Rodriguez's tenure with the Yankees was over. Rodriguez would later call the opt-out a "huge debacle" and a "mistake that was handled extremely poorly."
Seeking to repair the relationship and re-open negotiations, A-Rod approached the Yankees through a Goldman Sachs managing director, and the two sides were able to work out a new deal in mid-December. That deal was the richest free-agent contract in MLB history. Rodriguez would go on to lead the Bronx Bombers to their 27th World Series championship in 2009. "All along," A-Rod said after reaching his new deal, "I knew I wanted to be a Yankee."
5) Alex Rodriguez, Rangers: 10 years, $252 million (2001-10)
Rodriguez's first free-agent megadeal -- the one he signed with the Rangers before the 2001 season -- ranks right behind his one with the Yankees. It pried him away from the Mariners at age 25, and at the time completely shattered the record for the largest free-agent contract, more than doubling Mike Hampton's $121 million deal with the Rockies that had been completed just days before Rodriguez's agreement was reached. In fact, it also doubled the largest professional sports contract to that point, Kevin Garnett's $126 million contract with the NBA's Timberwolves signed in 1997.
A-Rod played only the first three seasons of that contract in Texas before he was traded to the Yankees, but for his part, he lived up to the deal. Rodriguez averaged 52 home runs and 132 RBIs with the Rangers -- leading the American League in homers all three years -- with a 1.011 OPS from 2001-03. He won the AL MVP Award in '03. Rodriguez kept up the pace after he was traded to New York, winning two more MVP Awards in '05 and '07 (although his postseason struggles at times caused a lot of consternation among Yankees fans).
6-T) Anthony Rendon, Angels: 7 years, $245 million (2020-26)
Rendon was considered the best position player on the free-agent market this offseason, and he got paid like it. He became just the sixth player to be an All-Star for a team that won the World Series, then leave in free agency that offseason (can link here -- https://www.mlb.com/news/players-who-left-after-world-series-win)). Rendon is one of two position players with six-plus WAR in each of the last three seasons, per FanGraphs. The other? His new teammate Mike Trout.
Rendon’s $35 million average annual value is the highest ever for a third baseman and tied for third highest regardless of position, with Strasburg. The only AAV higher? Cole’s $36 million and new teammate Trout’s $35.5 million.
6-T) Stephen Strasburg, Nationals: 7 years, $245 million (2020-26)
When Strasburg opted out of his existing contract after winning the 2019 World Series, he still had $100 million due to him over four years. It turned out to be a highly lucrative decision. While Strasburg appeared to be far from certain to opt out when the season began, he proceeded to produce arguably his finest year, leading the NL in innings (209) and wins (18), posting a 3.32 ERA and 251 strikeouts while finishing fifth in the Cy Young Award race. He then put together one of the more spectacular postseason runs in history, culminating in a World Series MVP Award.
Even once Strasburg was on the open market, the Nats remained the consensus favorites for the services of the pitcher they picked No. 1 overall in 2009. Not only did Washington retain Strasburg, but it rewarded him with a contract that at least temporarily set records for total dollars and average annual value ($35 million) for a pitcher, besting David Price and Zack Greinke, respectively.
8-T) Albert Pujols, Angels: 10 years, $240 million (2012-21)
Pujols was coming off a historically great 11-year run with the Cardinals when he hit free agency following the 2011 season. He was a three-time National League MVP Award winner ('05 and '08-09), a two-time World Series champ ('06 and '11), the '01 NL Rookie of the Year Award winner, a nine-time All-Star ('01, 2003-10), a back-to-back home run champion ('09-10) and a batting champion ('03). His accomplishments earned him a mega-deal with the Angels entering his age-32 season.
Injuries have sapped Pujols of his elite production since he arrived in Anaheim, and the amount of money the Angels have to pay him through his decline have caused many to criticize the contract. But Pujols also has over 1,000 hits with the Angels -- making him one of just nine players in MLB history with 1,000 hits in both leagues -- and close to 200 homers, including a 40-homer season and a pair of 30-homer seasons. He's reached several career milestones in Anaheim: 500 and 600 home runs, as well as 3,000 hits. Pujols' best years came with the Cardinals, but he's further cemented his Hall of Fame legacy with the Angels.
8-T) Robinson Canó, Mariners: 10 years, $240 million (2014-23)
Cano signed his contract with Seattle at age 31 after spending the first nine years of his career with the Yankees. In New York, he was a five-time AL All-Star, a five-time AL Silver Slugger Award winner and two-time Gold Glove Award winner at second base, as well as winning the World Series in 2009. He continued to excel with the Mariners, earning All-Star nods in three of his first four seasons in Seattle. Cano, now a member of the Mets, is sitting on 2,570 career hits entering his age-37 season in 2020, which gives him a shot at 3,000. He's on a potential Hall of Fame track, although his suspension for violating MLB's performance-enhancing drug policy in 2018 might cast a shadow over his case.
"I want to earn every penny that I get here," Cano said at the beginning of 2018. "I don't want to be like those guys that, two or three years into their contract, they do really good and then they don't care. I do care. … That's how I want to be remembered, as a guy that was productive in this game, not a guy that just feels comfortable because he gets the money."
10) David Price, Red Sox: 7 years, $217 million (2016-22)
Before Strasburg, the largest free-agent contract ever awarded to a pitcher belonged to Price, who joined a small group of $200 million pitchers -- Zack Greinke, Max Scherzer and Clayton Kershaw are the others -- when he went to Boston in the offseason of 2015. The left-hander was 29 when he signed the deal after spending his first eight Major League seasons with the Rays (with whom he won the AL Cy Young Award in '12), Tigers and Blue Jays.
For a while, Price wasn't always the most popular player with Red Sox fans -- especially due to postseason struggles and a verbal altercation with NESN broadcaster and Hall of Fame pitcher Dennis Eckersley in 2017 -- but he reversed all those narratives in the 2018 World Series. Price was brilliant in winning both Game 2 and the clinching Game 5 over the Dodgers, leading the Red Sox to their fourth championship in 15 seasons.
Total value isn't the only way to look at player contracts, as the length of the deal also matters. Here's a list of the biggest MLB free-agent contracts by the amount they were worth per year.
Top 10 free-agent contracts by average annual value
1) Gerrit Cole, Yankees: $36 million (2020-28)
2-T) Stephen Strasburg, Nationals: $35 million (2020-26)
2-T) Anthony Rendon, Angels: $35 million (2020-26)
4) Zack Greinke, D-backs: $34,416,666 (2016-21)
5) David Price, Red Sox: $31 million (2016-22)
6-T) Manny Machado, Padres: $30 million (2019-28)
6-T) Max Scherzer, Nationals: $30 million (2015-21)
8) Roger Clemens, Yankees: $28,000,002 (2007)
9-T) Alex Rodriguez, Yankees: $27.5 million (2008-17)
9-T) Yoenis Céspedes, Mets: $27.5 million (2017-20)
David Adler is a reporter for MLB.com based in New York. Follow him on Twitter at @_dadler.