Aces for hire: Max Scherzer, Gerrit Cole and the best free agent pitchers ever

[Editor’s Note: Follow the New York Yankees vs. the defending champion Washington Nationals in the opening game of the 2020 season.]

There’s a new ace in New York. Gerrit Cole, the 29-year-old flamethrower who helped the Houston Astros to the World Series, will make his debut for the Yankees Thursday against the Washington Nationals on MLB’s opening night.

It’s a moment nine months in the making. Cole inked a nine-year, $324 million contract with New York on Dec. 10, 2019. The contract is the richest ever for a pitcher in terms of overall value, and will undoubtedly put Cole under a microscope from day one.  

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It also got us to wondering: A decade from now, where will Cole’s contract ultimately land on the success scale?

Dozens of top-tier pitchers have signed big money contracts in free agency. Some have even signed multiple big-money deals. Some of those deals have paid off. Some have completely backfired. Overall, they have created almost as many headaches as they have elicited smiles.

The bar will be high in New York. Yankees fans have huge expectations for Cole, and will hope his contract ends up among the best big-ticket deals of all-time. To provide some perspective on the bar Cole is now aiming for, we’ve decided to look back at what may be the five best big-money contracts signed by a pitcher.

<a class="link rapid-noclick-resp" href="/mlb/players/8193/" data-ylk="slk:Max Scherzer">Max Scherzer</a> has lived up to his massive by winning two Cy Young awards and leading the Washington Nationals to the franchise's first-ever World Series title. (Photo by Cooper Neill/MLB Photos via Getty Images)
Max Scherzer has lived up to his massive by winning two Cy Young awards and leading the Washington Nationals to the franchise's first-ever World Series title. (Photo by Cooper Neill/MLB Photos via Getty Images)

Max Scherzer — Washington Nationals

Signed seven-year, $210 million contract on Jan. 21, 2015

Who better to start with than Cole's opening day opponent? It's been five years since Scherzer signed with Washington, and those five years have arguably been the most productive by a free agent pitcher during any era. 

Since 2015, Scherzer has gone 79-39 with a 2.74 ERA and 1,371 strikeouts in 1,050 2/3 innings. He won the NL Cy Young in 2016 and 2017, and was a historically dominant Jacob deGrom season in 2018 away from making it three straight. That's after winning the AL Cy Young with Detroit in 2013. 

Despite neck and back issues in 2019, Scherzer powered through to another top three Cy Young finish. In October, Scherzer was in true ace form, finishing with a 2.40 ERA in 30 innings. Though his back still wasn't 100 percent, Scherzer helped lead Washington to its first championship with gutsy outings in Game 1 and 7 of the World Series.

It almost doesn't matter what Scherzer does the next two seasons. This contract has been a bargain for Washington and this run has likely punched Scherzer's ticket to Cooperstown. 

Nolan Ryan — Houston Astros

Signed four-year, $4.5 million contract on Nov. 19, 1979

That contract wouldn't even land you a decent No. 4 starter here in 2020. Back in 1979 though, Ryan's deal with the Houston Astros raised the bar as he became the first player in MLB history to earn more than $1 million in a season.

At the time, a 32-year-old Ryan was already 13 years into his Hall of Fame career. It was this stretch though that almost certainly cemented his legacy. During the length of his contract, Ryan tossed 24 complete games, 10 shutouts and one no-hitter while posting a 2.91 ERA in 120 starts. In the strike-shortened 1981 season, he led MLB with a 1.69 ERA. 

Ryan remained with Houston for another five seasons, and remained one of the game's best hurlers into his 40s. Cole is on a similar path. Though we’ve yet to see if he’ll prove as durable as the Ryan Express.

Greg Maddux won the NL Cy Young award during his first three seasons with the <a class="link rapid-noclick-resp" href="/mlb/teams/atlanta/" data-ylk="slk:Atlanta Braves">Atlanta Braves</a>. (Andy Lyons/Getty Images)
Greg Maddux won the NL Cy Young award during his first three seasons with the Atlanta Braves. (Andy Lyons/Getty Images)

Greg Maddux — Atlanta Braves

Signed five-year, $28 million contract on Dec. 9, 1992

If Scherzer isn't the greatest free agent signing in MLB history, then it's probably Greg Maddux. After winning his first Cy Young with the Chicago Cubs in 1992, "Mad Dog" won three more in '93, '94 and '95. In the ‘95 postseason, Maddux posted a 1.70 ERA in 37 innings, helping lead Atlanta to its lone World Series title during its historic run of 14 straight division championships. 

Over the span of his contract, Maddux went 89-33 with a 2.13 ERA and 0.96 WHIP. His 39.0 WAR during that five-year stretch is actually better than Scherzer's 34.5 WAR with Washington, so maybe that debate is settled right there.

Any way you slice it, this relationship was profitable for both sides. Overall, Maddux won 194 games during 11 seasons with Atlanta. In 29 postseason appearances, he posted an excellent 2.81 ERA. 

Signing Randy Johnson immediately turned the Arizona Diamondbacks into World Series contenders. (Photo by Stephen Dunn/Getty Images)
Signing Randy Johnson immediately turned the Arizona Diamondbacks into World Series contenders. (Photo by Stephen Dunn/Getty Images)

Randy Johnson — Arizona Diamondbacks

Signed five-year, $68.4 million contract on Dec. 10, 1998

After 10 brilliant seasons in Seattle — and a brief but excellent stint in Houston — the "Big Unit" reached another level of dominance in Arizona. Over the first four seasons of his contract, Johnson won four straight NL Cy Young awards, averaged 354 strikeouts, and posted a collective 2.48 ERA and 1.04 WHIP. 

In 2001, Johnson found yet another gear during the postseason, winning five decisions — including two shutouts — while finishing with a 1.52 ERA. Johnson came out of the bullpen in Game 7 of the World Series against the New York Yankees, earning the win with a scoreless inning and a third. 

In 2002, Johnson won 24 games. In 2003, which was the final year of his contract, the then 39-year-old left-hander was limited to just 18 starts after undergoing knee surgery. It was a tough way to end the contract, but Johnson did stick around and bounce back in his age-40 season for Arizona, posting a 2.60 with 290 strikeouts in 245.1 innings. In other words, when healthy, Johnson was a workhorse and bargain for the D-backs.

Kevin Brown signed one of the best free agent contracts for a pitcher and also one of the worst. (Getty Images)
Kevin Brown signed one of the best free agent contracts for a pitcher and also one of the worst. (Getty Images)

Kevin Brown — Florida Marlins

Signed three-year, $12.6 million contract on Dec. 22, 1995

You wouldn't believe it now, but the Marlins have had success in free agency. Most notably, the team struck gold by signing Kevin Brown prior to the 1996 season. 

Brown, then 30, was in the prime of his prime during this contract. In year one, he led the NL in ERA (1.89) and WHIP (0.94), while finishing second only to John Smoltz in the Cy Young voting. In year two, he pitched a no-hitter in San Francisco, made the All-Star team and helped lead the Marlins to their first World Series title. 

Before year three, Brown was actually traded to San Diego. That was on brand for the Marlins even in 1998. But he finished the bargain deal strong, posting a 2.38 ERA in 257 innings. That season, Brown finished third in the Cy Young voting. All in all, it is undeniably among the best free agent deals for a pitcher. 

It must also be noted that Brown signed a deal that history remembers less favorably immediately after this one expired. Brown joined the Los Angeles Dodgers on a seven-year, $105 million deal prior to the 1999 season. That made him the first $100 million player in baseball. Three years into that deal, Brown tore a muscle in his right elbow and was never the same. Over his final five seasons, Brown only topped 22 starts once.

Brown’s second deal illustrates how quickly a long-term, big-money commitment can go south. Cole’s deal being nine years also makes it far less likely he’ll be able to sustain dominance for the length of the contract. However, if he can have five years like Scherzer, Maddux or even Johnson, the Yankees should be happy.

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