MLB Free Agency: Cliff Lee and the 20 Most Coveted Free Agent Pitchers Ever

Ronald Martinez/Getty Images

You can never have too much pitching. Pitching wins championships. Momentum is only as good as your next day's starting pitcher. General managers, broadcasters and baseball columnists tell us as much each and every year, and each and every year these beliefs are reinforced when the biggest Free Agent starter on the market is signed to a massive contract that takes him into his late 30s.

No player on the field can have more impact on a game than a dominant starting pitcher. It's no surprise then that over the past 35 years, pitchers have consistently ranked as some of the most highly paid players in the game.

This offseason, former Ranger Cliff Lee, perhaps the second best pitcher in the game, is a free agent. The Rangers want Lee back and are willing to pay. The Yankees, a team Lee helped knock out of the playoffs, also want his services and a mystery team has supposedly stepped up with a seven-year offer for $20-$25 million a year.

We all know about Lee. He's undeniably one of the best free agent pitchers in the history of baseball, but his situation is far from unique. Let's take a trip back in time, starting in 1975, to look at a time-line of the most coveted free agent pitchers ever.

Catfish Hunter, 1975

A year before the reserve clause was struck down, Catfish Hunter became baseball's highest paid player after a breach of contract by A's owner Charles Finely led an arbitrator to declare Hunter's contract with the team void.

One of the league's best pitchers, Hunter had led the AL with 25 wins and a 2.49 ERA to win the 1974 Cy Young award. He had finished third and fourth in Cy Yong voting in 1972 and 1973.

Hunter hit the open market during the offseason and the bidding ensued. Almost every team in baseball offered him a contact, and it became clear he would break the million dollar ceiling—a first for baseball. He eventually signed with the New York Yankees for five years and $3.75 million—an astronomical contract for a baseball player at the time.

Hunter would again lead the league in wins in 1975 and win another 17 games in 1976. However, he sharply declined after that and retired when his contract was up at just 33-years-old.

Goose Gossage, 1978

Jim McIsaac/Getty Images

The second pitcher on this list also signed with the New York Yankees, two years after Hunter and a year after the reserve clause was struck down, allowing Major League players to become free agents.

Goose Gossage, Hall of Fame closer, took advantage of his free agency to become one of the games highest paid players.

The prototypical relief ace, Gossage led the National League in saves in 1975, finishing sixth in Cy Young voting. The next year Pittsburgh moved Gossage into the starting rotation. Goose struggled, and the Pirates moved him back to the bullpen in 1977.

That year, Gossage pitched 133 innings in relief, saving 26 games with a 1.62 ERA and 151 strikeouts. Gossage hit the open market following the '77 season, and the New York Yankees snatched him up, paying him $2.75 million over the next six seasons.

Gossage would again hit free agency in 1983, leaving the Yankees for San Diego but remaining the games highest paid closer for several seasons thereafter.

Nolan Ryan, 1980

Pool/Getty Images

Four years after the reserve clause was struck down, future Hall of Famer Nolan Ryan became a free agent. One of the best and most celebrated pitchers in the game, Ryan had led the league in strikeouts in seven of the past eight seasons. At just 32, Ryan seemed a near lock to break Walter Johnson's decades-old strikeout record and was sure to draw crowds and win games wherever he went.

While Hunter's contract was the first to total more than a million dollars, it had only paid an annual salary of $150,000, and most of the money had gone to a signing bonus paid to Catfish in 1975. In the offseason following 1978, Dave Parker had signed the first contract paying $1 million per season, but due to language in the contract, it was not widely known how much Parker was making.

Early in 1980, Nolan Ryan agreed to a four -ear, $4.5 million contract making him the first pitcher in baseball history ever paid more than a million dollars a year. Over the next eight seasons with the Astros, Ryan would win 106 games and strike out nearly 2,000 more batters, shattering Johnson's strikeout record in the process.

Mark Langston, 1989

Stephen Dunn/Getty Images

Though salaries exploded in the 1980s throughout baseball, most teams elected to sign their stars to large extensions and few elite players hit the open market. Salaries were still low enough that most teams could afford to retain their best players, and those that couldn't traded them to more competitive teams.

This all changed in the late 80s and into the early 90s, as players realized they could make much more money as free agent and salaries again went through the roof.

The offseason following 1989 was a crazy one for baseball. In November of that year, the Kansas City Royals extended ace Bert Saberhagen, signing him to a three-year, $7.9 million contract and making him baseball's highest paid player. Five days later, Kirby Puckett signed a three-year, $9 million contract, making him the highest paid player in the league and six days after that, Rickey Henderson signed a four-year, $12 million deal, matching Puckett's annual salary.

Then came Mark Langston. Langston burst onto the scene in the mid-80s, leading the league in strikeouts in three of his first four seasons. In 1988 and 1989, Langston struck out 235 batters in each season, winning a total 31 games.

At 28-years-old, Langston was a highly coveted starting pitcher in one of the most extreme free agent markets in the games history. The California Angels, who had been unable to lure Nolan Ryan back to Anaheim the previous year, offered Langston a record five year, $16 million contract.

Langston won 88 games over eight seasons for the Angels and made the All-Star team three times in his first five years in California.

Mark Davis, 1989

Scott Halleran/Getty Images

While Langston's contract shattered the Major League record, he wasn't the highest player in the league for long.

In December of 1989, the Kansas City Royals signed Mark Davis to a four-year contract worth $3.25 million a season, then a record high salary.

But Davis was not an ace starter like Mark Langston. Instead, he was a closer and one of the best closers in the league at that time.

The previous season, Davis had led the National League with 44 saves and won the Cy Young award, the last reliever to do so until 2003 (Eric Gagne).

The Davis contract was a disaster. Over the four years covered in the deal, Davis combined to save just 11 games with an ERA over 4.2 in all four seasons and an ERA over 5.00 for the life of the contract.

David Cone, 1992

Jim McIsaac/Getty Images

As good as the offseason following 1989 was for free agents, the offseason following the 1992 season witnessed several ace pitchers hitting the market at the same time and all of them getting paid.

The first of these ace pitchers to sign was David Cone, the former Met and Blue Jay. One of the most dominant pitchers in the game at the time, Cone had led the Majors in strikeouts in 1992. He also led the NL in strikeouts in 1992 and 1991.

Cone debuted as a Kansas City Royal in 1986, but was quickly traded to the Mets, where he spent the next five years. With Cone on the market, the Royals offered him a three-year, $18 million contract, bringing the righty back home to join Bert Saberhagen in one of the leagues best rotations.

Over $100 million was committed by Major League teams on the day Cone signed, the first time teams had spent that much money in a 24-hour period. Cone would go on to win the 1994 Cy Young award before a trade sent him to the Yankees in 1995.

Greg Maddux, 1992

Brian Bahr/Getty Images

Probably the biggest free agent signing on this list, Greg Maddux was arguably the best pitcher in baseball when he left the Chicago Cubs in 1992 to sign with the Atlanta Braves.

Maddux was coming off his first Cy Young award and a season in which he won 20 games with a 2.18 ERA. He was also just 26-years-old, and outside of Barry Bonds, the most coveted free agent on the market.

The Atlanta Braves signed Maddux to a five-year, $28 million contract, making him one of baseball's highest paid pitcher. Incredibly, Maddux had an offer of five years, $37 million on the table from the New York Yankees, but instead, signed with Atlanta, a far more competitive team at the time.

The move worked out for the Braves. Maddux won the next three Cy Young awards, with an ERA under 2.00 from 1993 to 1995.

Jimmy Key, 1992

Otto Greule Jr/Getty Images

Jimmy Key was yet another beneficiary of the spending binge in late 1992.

Entering the winter of 1992, the New York Yankees had targeted three free agents, arguably the three best on the market. Greg Maddux, Barry Bonds and David Cone were all major targets of the Yankees front office, and they had plenty of money to spend.

But when all three free agents turned them down, the Yankees turned to Key as a fallback option. At 31, Key had spent nine years with the Toronto Blue Jays, and despite a couple of down seasons in the late 80s, had been one of the leagues best pitchers over his career in Toronto.

The Yankees offered him a four-year, $17 million deal, and Key accepted. He would finish fourth and second in Cy Young voting over the next two seasons. Key quickly declined after that but still managed to lead the Yankees to the 1996 World Series.

Roger Clemens, 1996

Dave Sandford/Getty Images

Following the 1996 season, the Boston Red Sox decided to part ways with their ace, 33-year-old Roger Clemens. According to the Red Sox, Clemens was in the "twilight of his career." Clearly, not all teams thought so.

Clemens was among the biggest names in baseball in the mid-90s, and while he'd had a couple of tough seasons, he led the league in strikeouts in 1996. On the open market, several teams bid on Clemens, but he settled for a three-year, $24.75 million deal with Toronto, making him baseball's highest paid pitcher.

He would win the next two Cy Young awards, another Cy Young award in New York and yet another in Huston, pitching effectively and at times dominating until he retired following the 2007 season.

Randy Johnson, 1998

Stephen Dunn/Getty Images

By the time Randy Johnson hit free agency in 1998, he was widely considered one of the best players in baseball, and despite being 34-years-old, was one of the most covetted players on the market.

The previous year, Johnson had 10-1 with a 1.28 ERA down the stretch for the Huston Astros, receiving Cy Young consideration for the fifth time in the past six seasons.

Shortly after Mo Vaughn became baseball's highest paid player, Johnson became baseball's highest paid pitcher in late 1998, signing a four-year deal worth over $52 million.

His title would not last long.

Kevin Brown, 1998

Al Bello/Getty Images

Shortly after Johnson signed his contact in Arizona, Kevin Brown shocked the baseball world by shattering all previous contract records.

Brown came up with Texas in the late 80s but bounced around a bit, playing for Baltimore, Florida and San Deigo between 1995 and 1998. This was not for a lack of talent.

In 1996, Brown led the league in ERA—an astounding 1.69. The following year, he led the Marlins to their first World Series tittle. A fire-sale landed him in San Diego, where he again dominated, with a 2.38 ERA, 18 wins and another trip to the World Series.

That offseason, Brown signed with the Los Angeles Dodgers for a record seven years, $105 million, becoming the first $100 million player in baseball history, and at $15 million a year, by far the highest paid in the league.

Mike Mussina, 2000

Jim Rogash/Getty Images

Amazingly consistent, Mike Mussina was one of the games best pitchers throughout the 1990s and was rewarded with a massive contract following the 2000 season.

Having finished in the Top Six in Cy Young voting in eight of the previous 10 seasons, Mussina was a highly coveted free agent, and at 31, much younger than Randy Johnson and Kevin Brown had been a year before.

The New York Yankees went hard after Mussina, and eventually signed him to a contract worth $88.5 million over the next six seasons.

Mike Hampton, 2000

Brian Bahr/Getty Images

Long the standard to which bad contracts are compared, Mike Hampton's massive eight-year deal with the Rockies following the 2000 season made him the highest paid player in baseball and the worst contract bust in baseball history.

Hampton entered the new millenium as one of the leagues best pitchers. In 1999, he won 22 games with the Astros, and after a solid season with the Mets in 2000, he was one of the most coveted players on the market.

Known to limit home runs, Hampton seemed like as good a fit as anyone for the harsh environment of Coors field. Coors in 2000 was about as offensive-friendly as any ballpark has ever been, and the Rockies envisioned Hampton as an ace that could get them a considerable edge in their home park. He was also just 27-years-old.

Coors probably played a role in the size of Hampton's deal, but the eight year, $120 million contract shocked people at the time and proved a major blunder over the next several seasons. Hampton compiled a 5.75 ERA for the Rockies over two seasons, was traded to the Braves and has dealt with injuries and ineffectiveness ever since.

Chan Ho Park, 2002

Ronald Martinez/Getty Images

Now nothing more than a middle reliever, Chan Ho Park was once one of the better pitchers in baseball, one of the first examples of professional players from Asia being imported to the United States and succeeding.

Park started his career with the Los Angeles Dodgers, were he pitched from 1995 to 2001. While not an ace of the Johnson, Clemens, Brown caliber, Park consistently pitched near 200 innings a year, won 13-16 games and posted ERA's in the mid-3s.

The Texas Rangers, who had shocked the world by offering Alex Rodriguez 10 years and $252 million the offseason before, desperately needed pitching help in their new stadium and offered Park a contract of five years, $65 million. In three seasons with Texas, Park never posted an ERA under 5.00.

Pedro Martinez, 2004

Michael Heiman/Getty Images

The best pitcher in baseball through the late 90s and early part of this last decade, Pedro hit free agency for the first time in 2004, shortly after leading the Red Sox to their first World Series title in 86 years.

While Pedro was still among the best pitchers in all of baseball, and one of the biggest names in the sport, he was also getting up there in age. 2004 had been a down year by his standards; the Red Sox did not want to offer him a four-year contract.

The New York Mets and new GM Omar Minaya offered Pedro a four-year, $53 million contract, and Pedro headed to Queens.

While the deal looked like a genius move in 2005—Pedro won 15 games with a 2.82 ERA and led the league in WHIP—he struggled over the next few seasons with injuries.

Roger Clemens, 2004-2007

Scott A. Miller/Getty Images

Perhaps no pitcher was as dominant for as long as Roger Clemens, and so it's probably fitting that Clemens is the only pitcher to appear on this list twice.

After his two Cy Young seasons in Toronto, Clemens spent 1999 through 2003 with the New York Yankees, winning two World Series, and appearing in four and also winning another Cy Young award.

After the 2003 World Series, Clemens announced his retirement. But before the 2004 season began, with friend and teammate Andy Pettitte in Houston with the Astros, Clemens came out of retirement to sign with his hometown team.

This was just the start of the insanity. Following a 2004 season in which Clemens won his seventh Cy Young award, he again wavered before resigning with Houston as baseball's highest paid player. An even better year in 2005 looked like his final season, but a month into the 2006 season, Clemens again returned to the Astros as baseball's highest paid player.

2006 again looked like Clemens' final season, but a month into 2007, he returned, this time as a New York Yankee, signing an incredible $28 million deal. The Boston Red Sox had offered Clemens about $18 million ,pro rated, and the Astros had also been in that vicinity.

Daisuke Matsuzaka, 2007

Jim Rogash/Getty Images

When Daisuke Matsuzaka was posted in the fall of 2007, the top teams in baseball lined up to pay inordinate sums just for the right to negotiate with the Japanese ace who had dominated competition in the WBC.

The Yankees, Red Sox and Mets all offered tens of millions of dollars to Daisuke's Japanese team for the right to negotiate a deal with Matsuzaka, and the Red Sox won with an incredible $50 million bid.

The Red Sox signed Dice-K to a six-year, $52 million contract on December 14th. While Matsuzaka had some initial success, he has been mostly a disappointment, struggling with injuries and ineffectiveness the past two seasons.

Barry Zito, 2007

Justin Sullivan/Getty Images

As big as Matsuzaka's deal was, it was nothing compared to the mammoth contract Barry Zito signed that offseason.

After bursting onto the scene in 2000 with the Oakland A's and winning the 2002 Cy Young award at just 24-years-old, Zito's free agency had been long discussed and long anticipated. But Zito had struggled mightily in 2004, and his 2005 and 2006 season had not been up to par with his dominance earlier that decade.

Zito was still 28 when he hit the market, and given his incredible early success in Oakland and consistently good performance over the past couple of years, he was highly coveted around the league.

The San Francisco Giants lured Zito across the bay with an offer of seven years, $128 million. Over the past four years in San Francisco, Zito has an ERA of 4.45.

CC Sabathia, 2009

Jim McIsaac/Getty Images

CC Sabathia had long been one of the best pitchers in baseball, but he really put things together in the two years leading up to his free agency.

In 2007, Sabathia led the American League in innings pitched and strikeout-to-walk ratio in 2007, winning the AL Cy Young award. In 2008, he struggled out of the gate, but 11-2 with a 1.65 ERA and seven complete game in the second half with Milwaukee.

The Yankees, who had passed on a trade for Johan Santana the previous year, offered Sabathia a seven-year, $161 million deal, and the Brewers ace bolted for New York.

Sabathia was instrumental in the Yankees 2009 Championship and led the AL in wins in both 2009 and 2010.

Cliff Lee, 2010

Ronald Martinez/Getty Images

That brings us to Cliff Lee.

If history tells us anything, it's that we know nothing. And as good as Cliff Lee has been, he could be an extremely expensive flop.

Still, Lee is not a good player caught in a great market. He's a great player who would be paid like one of the best pitchers in baseball in any market.

I expect Lee to sign with the Yankees, or possibly the Rangers, for six years and between $120 and $150 million, putting his deal right up there with Sabathia's.

Long term, the deal might not look so great, but in the short term I expect Lee to contribute greatly to whatever team signs him and ultimately go down as a free agency success.