Starting with Catfish Hunter's landmark contract for the 1975 season, let's go back and find the pitchers who set the marks for highest total value contract.
Dec. 31, 1974: Catfish Hunter, five years, $3.2 million (Yankees)
Quote: "I hung up the phone, turned to my wife and said, 'We don't belong to anybody.' I was scared. I didn't have a job. I didn't realize the implications." -- Hunter
Hunter became baseball's first free agent in the modern era due to carelessness or, more likely, abject hubris on the part of A's owner Charlie Finley. In 1974, players were still bound to their teams by the reserve clause, which anchored a player to his team with little negotiating power. That was challenged in 1975, opening the door for the free-agent era to begin following the 1976 season, but Hunter's case was different.
He had a clause in his contract that required Finley to make payments into a long-term annuity, but Finley was late in making the payments. Arbitrator Peter Seitz -- who also would strike down the reserve clause -- declared Hunter's contract had been violated, making him a free agent.
Hunter had been the ace of three straight World Series champs for the A's, and he was regarded as one of the best pitchers in the game. (He had won the 1974 Cy Young Award after going 25-12 with a 2.49 ERA.) After making $100,000 in 1974, his new contract paid him about $640,000 per season. (Initial reports at the time estimated a $3.75 million total package, with later reports listing $3.5 million or $3.2 million, which seems to be the figured cited most often now.)
How it worked out: Hunter was great in 1975, leading the American League with 23 wins, posting a 2.58 ERA and finishing second in the Cy Young voting. He also pitched 328 innings and threw 30 complete games. It would be his last great season. He produced just 1.9 WAR over his final four campaigns, although he did help the Yankees to three straight AL pennants, and he was the winning pitcher in the clinching Game 6 of the 1978 World Series.
INTERLUDE: In November 1977, Pirates reliever Goose Gossage signed with the Yankees for what was initially reported as a six-year, $3.6 million contract. Later reports adjusted that figure down to $2.75 million. Accurate details from this era can be difficult to establish, and many of the contracts contained complicated deferrals or personal-service deals. Either way, at the minimum Gossage did not top Hunter's annual average value.
Nov. 19, 1979: Nolan Ryan, four years, $4.5 million (Astros)
Quote: "Nolan Ryan can be replaced by two 8-7 pitchers." -- Angels general manager Buzzie Bavasi
Ryan wasn't the best pitcher in the game in 1979, but he certainly was one of the most famous, having tied Sandy Koufax's mark of four no-hitters and setting all kinds of strikeout records along the way. In 1979, he led the AL in strikeouts for the seventh time in eight seasons, but he had finished 16-14 with a 3.60 ERA, slowing down in the second half with a strained muscle near his right elbow. Even though the Angels had made the playoffs for the first time in franchise history in 1979, Bavasi -- having cited Ryan's win-loss record and age (he would be 33 in 1980) -- figured his best seasons were behind him. Ryan would last "just" 14 more years.
How it worked out: Ryan's contract called for a guaranteed $3.5 million over three years, with a $1 million club option for the fourth year. It was big deal and landed Ryan on the cover of every baseball preview magazine that spring. After all, he became the first professional team sport athlete with a $1 million annual salary. He would go 52-36 with a 2.91 ERA those four seasons, leading the Astros to their first playoff appearance in 1980 -- a gut-wrenching National League Championship Series loss to the Phillies in which Ryan couldn't hold a 5-2 lead in the eighth inning of the final game.
Ryan would win an ERA title in 1981 as the Astros again made the playoffs, and he remained in Houston through 1987. He wasn't the best pitcher in the game -- Baseball-Reference ranks him just 17th in WAR over those first four seasons -- but the contract helped establish Ryan as a legendary figure in the game's history.
Jan. 7, 1984: Goose Gossage, five years, $6.25 million (Padres)
Quote: ''Now the starters will be able to go as hard as they can for as long as they can." -- Gossage
Hey, that sounds like a quote from 2019, not 1984! It also suggests that even in the early 1980s, starting pitchers were holding a little something back in order to pitch deeper into games. Gossage had compiled a 2.10 ERA in six seasons with the Yankees but had informed the Yankees he would "not return and play for George Steinbrenner."
Gossage hit free agency at a time when closers -- or stoppers, as they were more commonly called then -- were a relatively new phenomenon and generally overrated in relation to their actual value, annually contending and even winning Cy Young Awards in the decade (and into the early 1990s). That helps explain why a reliever could get the biggest contract ever for a pitcher.
How it worked out: Gossage had two good seasons, helping the Padres reach the World Series in 1984, where Kirk Gibson treated him rather rudely. His relationship with the Padres soured in 1986 when he said team president Ballard Smith "doesn't know anything and doesn't care" and wanted "choirboys and not winning players." The Padres attempted to suspend him for insubordination. After declining seasons in 1986 and 1987, he was traded to the Cubs.
Dec. 7, 1984: Bruce Sutter, six years, $9.1 million (Braves)
Quote: "Their concern," a baseball official said of the owners, "was whether the Atlanta club would be able to meet the financial obligations, and what effect it might have on baseball."
The structure of Sutter's contract was a hot mess, so convoluted that Ted Turner's fellow owners voted to censure him after the deal was announced. During the six seasons, Sutter would earn $750,000 per season -- but those were only interest payments. The rest of the money would be paid out over 30 years from a deferred payment account, in annual installments of $1.3 million after the six-year contract ended. Yes, Sutter is still getting paid.
Dan Lewis of The Athletic explained:
And because all of the money he's earned to date (and will earn through 2021) is interest, that $9.1 million in principal has, to date, gone unpaid. That's right: It was deferred until 2022. Four years from now, Bruce Sutter will be a 69-year-old Hall of Fame pitcher who last pitched in 1988 who, unlike Bobby Bonilla, will be on the receiving end of a $9.1 million check from the Atlanta Braves.
In total, Sutter will earn north of $45 million for his three years being terrible as a member of the Atlanta Braves. Bobby Bonilla, eat your heart out.
Was Sutter's contract a new record? I guess that's open for debate. Estimates at the time suggested Turner would only require an initial investment of $1.7 million to fund the annuity. It's not clear whether the Braves actually did this or whether they simply write a check every year to Sutter.
How it worked out: It didn't. Sutter had a 4.55 ERA with the Braves, missing all of 1987 and then retiring after the 1988 season. Even though he retired with two years left on the contract, his money was guaranteed.
Dec. 14, 1984: Rick Sutcliffe, five years, $9.5 million (Cubs)
Quote: "There was unfinished business. I wanted to come back and get us into the World Series." -- Sutcliffe
The Cubs had acquired Sutcliffe from the Indians in June 1984, and he went 16-1 with a 2.69 ERA, helping the Cubs to the NL East title and edging out Dwight Gooden for Cy Young honors. Sutcliffe stayed with the Cubs, picking them over the Padres. The contract was paid out over 12 years, so even Sutcliffe's agent declared, "It depends how you look at it," when asked if Sutcliffe was the highest-paid pitcher.
How it worked out: Fair. Sutcliffe went 60-57 with a 3.82 ERA, leading the NL with 18 wins in 1987 and making the All-Star team in 1987 and 1989 (when the Cubs won another division title). He ranked 17th in the majors in WAR over that span.
INTERLUDE: It appears Sutcliffe's mark held for several years, as owners engaged in collusion to prevent higher salaries following the 1985, 1986 and 1987 seasons. Depending on how you might value the Sutter and Sutcliffe deals, in 1989 the following pitchers might all be considered for title of highest-paid pitcher:
Feb. 8: Dwight Gooden, three years, $6.7 million (Mets)
Feb. 15: Roger Clemens, three years, $7.5 million (Red Sox)
Feb. 17: Orel Hershiser, three years, $7.9 million (Dodgers)
April 19: Frank Viola, three years, $7.9 million (Twins)
Nov. 17: Bret Saberhagen, three years, $8.9 million (Royals)
Then came a big one ...
Dec. 1, 1989: Mark Langston, five years, $16 million (Angels)
Quote: "The five years and the no-trade provision were important. Mark and I knew this would have an impact on other players. We wanted to send a message to other players that it could be done." -- agent Arn Tellem
Langston had gone 16-14 with a 2.74 ERA for the Mariners and Expos in 1989, throwing 250 innings and ranking second in the majors in strikeouts. An athletic lefty with a big heater, his five-year contract was the first for any player since Eddie Murray signed his deal in 1985. Thanks, collusion.
How it worked out: Pretty well. After a rough first season with the Angels (10-17, 4.40), he was much better and went 65-58 with a 3.66 ERA in five years on mostly bad Angels teams (they never finished above .500 from 1990 to 1994), making the All-Star team in 1991, 1992 and 1993. He ranked eighth in WAR, 10th in innings and sixth in strikeouts in the five years.
Feb. 8, 1991: Roger Clemens, four years, $21.52 million (Red Sox)
Quote: "I'm sure it's a good thing for Roger Clemens. I'm not sure it's a good thing for the rest of baseball." -- Mets executive Al Harazin
With collusion in the rear-view mirror, national TV contracts escalating in value and attendance increasing across the sport, baseball salaries were rapidly going up. Clemens, coming off a season when he went 21-6 with a 1.93 ERA, had one year left until free agency when the Red Sox extended him, making him baseball's first $5 million player. The contract included an option year for 1996, so it ended up as a five-year deal worth just over $26 million, covering 1992 to 1996.
How it worked out: It did -- sort of. Clemens ranked fourth in WAR, fifth in ERA+ and third in strikeouts, but he went just 58-50 with a 3.43 ERA (40-39 over the final four years), numbers that were short of what he had done in 1990 and 1991 (when he won his third Cy Young Award). Other than a playoff run in 1995, it wasn't a great era for the Red Sox. And at the end of the deal, general manager Dan Duquette wondered whether Clemens was in the "twilight" of his career -- even though he had led the AL in strikeouts in 1996.
Dec. 10, 1992: Greg Maddux, five years, $28 million (Braves)
Quote: "This one hurts. He's the best one out there. I never thought I could say this. But he's a steal at $28 million. He's a steal." -- Yankees general manager Gene Michael
The 1992 NL Cy Young winner with the Cubs after going 20-11 with a 2.18 ERA, Maddux was heavily pursued by the Yankees. They offered $34 million, but Maddux took less to sign with the Braves, who were coming off back-to-back World Series appearances in what would be the first two seasons of their long dynasty.
How it worked out: Maybe the best free-agent signing ever. Michael was right. Maddux got even better, winning the next three Cy Young Awards to give him four in a row. From 1993 to 1997, Maddux went 89-33 with a 2.13 ERA, dominating in the heart of the steroid era with his pinpoint control. Over the five seasons he was a remarkable 8.3 WAR better than the No. 2 pitcher in that period (David Cone).
INTERLUDE: The Braves would keep their powerhouse rotation together. After winning the 1996 Cy Young Award, John Smoltz hit free agency and re-signed with the Braves for four years and $31 million. Early in 1997, they gave Tom Glavine a four-year, $34 million extension. It was Maddux's turn again.
Aug. 10, 1997: Greg Maddux, five years, $57.5 million (Braves)
Quote: ''This deal doesn't happen if there wasn't a shortage of pitching. Our industry is starved for pitching.'' -- agent Scott Boras
Sitting with a 15-3 record and 2.36 ERA in early August, the Braves locked up Maddux before he entered free agency. Maddux became the highest-paid player in the game, nearly doubling his average salary from his previous contract.
How it worked out: Again, superbly. Maddux went 89-44 with a 2.88 ERA from 1998 to 2002 as the Braves won five more division titles. While he wasn't as dominant as the previous five-year stretch, he still ranked fifth in WAR over the five years.
Dec. 12, 1997: Pedro Martinez, six years, $75 million (Red Sox)
Quote: "And he doesn't even have a jump shot." -- Unnamed baseball executive
That quote was a reference to rapidly escalating salaries in the NBA. One thing has always held true: Somebody is going to complain when a new standard is set. Duquette might have misfired on Clemens, but he redeemed himself in acquiring Martinez, who had just won the NL Cy Young Award in a breakout 9.0 WAR season with the Expos, and then signing him to a mega-extension. It almost didn't happen, though. At the time, Gordon Edes of the Boston Globe reported that the Red Sox had agreed to trading prospect Carl Pavano to the Marlins for closer Robb Nen; the Marlins had even alerted other teams that Nen was now off the block. Instead, Duquette pivoted and used Pavano to acquire Martinez.
How it worked out: Thank you very much. The extension covered 1999 through 2004. It was one of the best six-year runs in history, as Martinez went 98-30 with a 2.44 ERA and ridiculous 197 ERA+. He won four ERA titles and two Cy Young Awards, finishing second, third and fourth in other years. And in 2004, the Red Sox finally ended the curse.
Dec. 13, 1998: Kevin Brown, seven years, $105 million (Dodgers)
Quote: "I think this is dangerous for the competitive balance of the game. The fact that Kevin Brown will make more in the next seven years than our whole team in the next four is not good." -- Reds GM Jim Bowden
One of the most controversial contracts in baseball history, this deal enraged front offices throughout the game. "There is no appropriate comment," commissioner Bud Selig said. Just months earlier, the Dodgers had traded Mike Piazza rather than pay him. Now they made Brown the first $100 million player -- blowing past the $14 million annual salary barrier to reach $15 million in the process. Brown had been dominant the previous three seasons, including leading the Marlins and Padres to the World Series, but he was also 34 years old, albeit a pitcher who had never been on the disabled list.
How it worked out: Brown sometimes shows up on lists of worst free agents, but that was hardly the case. He went 58-32 with a 2.83 ERA in five seasons with the Dodgers, mixing in three great seasons with a couple of injury-shortened ones, before a trade to the Yankees. As for competitive balance, the Dodgers never made the playoffs in Brown's five years with the club.
Dec. 9, 2000: Mike Hampton, eight years, $121 million (Rockies)
Quote: "Announce the deal. He's an outstanding pitcher. It's a lot of money. Case closed. I don't want to hear about the Wheat Ridge [Colorado] school system." -- Sandy Alderson, MLB's executive vice president for baseball operations
This was Selig's "The sky is falling" period, and Alderson played along when Hampton cited the local school systems as a reason he signed with the Rockies. Hampton had gone 22-4 for the Astros in 1999 and 15-10 with a 3.14 ERA for the Mets in 2000, but he also had walked too many batters (200 of them) and didn't have a big K rate. It was a risky signing from the get-go ... even before factoring in Coors Field. Deferred money made the present-day value of the contract about $85 million.
How it worked out: Disastrous. Hampton actually made the All-Star team in his first season in Colorado, but he finished 14-13 and then went 7-15, 6.15 in 2002, earning a trade to the Braves (via the Marlins). Over the eight years, his total WAR was just 2.9.
Dec. 28, 2006: Barry Zito, seven years, $126 million (Giants)
Quote: "I think Barry Zito will be the face of the Giants franchise for a long time." -- Giants source
Zito had been a durable, crafty lefty with the A's, never missing a start with them, but outside of his Cy Young year in 2002 had been more of a No. 2 than an ace. Giants GM Brian Sabean believed that Zito, due to his style of pitching, would age well, comparing him to Greg Maddux. Oops.
How it worked out: Zito did not age like Greg Maddux, and the comparison was silly in the first place. He went 63-80 with a 4.62 ERA for the Giants, scratching out just 2.4 WAR over the life of the deal. He did have two big wins in the 2012 postseason, however, including beating Justin Verlander in Game 1 of the World Series.
Feb. 1, 2008: Johan Santana, six years, $137.5 million (Mets)
Quote: "He was special. It was my job to keep him that way." -- Mets manager Terry Collins
The Twins were determined to trade Santana before he hit free agency. The Red Sox wouldn't give up Jon Lester. The Yankees wouldn't part with Phil Hughes. The Mets gave up Carlos Gomez as part of their package and were allowed to first negotiate the record-setting extension for the pitcher then generally regarded as the best in the game. Santana had gone 70-32 with a 2.89 ERA and two Cy Young Awards over the previous four seasons.
How it worked out: Santana had three good seasons with the Mets, which covered the first two years of the extension, but missed all of 2011 after shoulder surgery. He returned in 2012 and threw the first -- and only -- no-hitter in Mets history on June 1, hurling 134 pitches in the process. He would make just 10 more starts in the majors.
Dec. 10, 2008: CC Sabathia, seven years, $161 million (Yankees)
Quote: "That's them, that's the Yankees, that's how we look at it. They operate in a world by themselves, and we understand that." -- Rockies GM Dan O'Dowd
After missing the playoffs in 2008 for the first time since 1993, the Yankees pulled out the checkbook, signing Sabathia, Mark Teixeira and A.J. Burnett as free agents, with Sabathia blowing away Santana's record for a pitcher. The contract included an opt-out clause after three years, which Sabathia exercised, and he then signed a five-year deal for $122 million.
How it worked out: The Yankees won the World Series in 2009, with Sabathia having a 6.2-WAR season and a big postseason. He earned 17.4 WAR over those first three years but wasn't the same ace-level starter under the five-year extension (and subsequent deals), and the Yankees haven't returned to the World Series since that 2009 campaign.
INTERLUDE: Sabathia's deal held for several years. Felix Hernandez signed a seven-year, $175 million extension with the Mariners in February 2013 (good for a few years, but the final four didn't go well), and Justin Verlander broke that the following month with a seven-year, $180 extension with the Tigers. Then came the first $200 million pitcher contract.
Jan. 17, 2014: Clayton Kershaw, seven years, $215 million (Dodgers)
Quote: "Big winner today ... me. I am blessed to catch best in the game for foreseeable future." -- Dodgers catcher A.J. Ellis
Just 25 at the time of the signing, Kershaw inked baseball's sixth $200 million deal, and his annual average salary of $30.7 million made him the highest-paid player. Kershaw had just gone 16-9 with a 1.83 ERA to win his second Cy Young Award in three seasons. He was the no-doubt best pitcher in the game and got the biggest contract; in fact, he reportedly had turned down a longer-term, $300 million offer from the Dodgers to take a shorter deal.
How it worked out: When your "bad" year is 16-5 with a 3.03 ERA, no regrets. Kershaw won Cy Young and MVP honors in his first year of the deal, and while he hasn't pitched 200 innings since 2015, he has gone 92-28 with a 2.27 ERA since the signing. He is third in pitcher WAR since 2014, trailing only Max Scherzer and Jacob deGrom. (He opted out of the original deal after 2018, and now he is entering the second year of a three-year, $93 million extension).
Dec. 4, 2015: David Price, seven years, $217 million (Red Sox)
Quote: "I was just saving all my postseason wins for the Red Sox. I know big things will happen to me in October. That just hasn't been the case thus far. That will change, and I've worked too hard. I know I can do it." -- Price
A workhorse with the Rays, Tigers and Blue Jays before reaching free agency, Price had finished second in the 2015 Cy Young voting but also was notorious for his struggles in the postseason.
How it worked out: How much is a ring worth? Price finally put those postseason demons behind him in 2018, helping the Red Sox win the World Series. In the regular season, however, he hasn't been the ace he was before coming to the Red Sox, with a 3.84 ERA and ranking just 34th in WAR since 2016. And now he has durability concerns moving into the final three years of the contract.
Dec. 9, 2019: Stephen Strasburg, seven years, $245 million (Nationals)
And one day later ...
Dec. 10, 2019: Gerrit Cole, nine years, $324 million (Yankees)
That's right, Strasburg's reign as baseball's highest-paid ace lasted all of one day and now the biggest pitching contracts in baseball belong to the two pitchers who cashed in this week in San Diego.
How will it work out?That is the $569 million question, but the Nationals and Yankees were willing to pay over half a billion dollars combined to find out the answer.
Kurkjian: Cole to Yankees makes them the best team in baseball
Tim Kurkjian says the Yankees' acquisition of Gerrit Cole makes them not only the best team in the American League but also the best team in baseball.