This annotated week in baseball history: Nov. 28-Dec. 4, 1998

On November 30, 1998, Randy Johnson signed with the Arizona Diamondbacks, one of the greatest pitcher contracts of all time. Richard looks at this and other deals.

I have always had a fondness for writing about bad contracts. In this year’s Hardball Times Annual—which is highly recommended, and can be purchased here—I revisit the concept of the “All-Bust” starting rotation. That is, those pitchers with the worst contracts in baseball history, an idea I have examined several times.

Of course, this is somewhat unfair, because while a lot of pitcher contracts have turned ugly over the years, there have also been a number of good deals. In the interest of presenting a fair perspective on these issues, this week’s column will look at some of the best pitching contracts of the past decade or so.

Before listing some of these contracts, it is worth pointing out that—much like getting rich here in the real world—there are two ways to a good pitching contract: lottery tickets and strong investments. (There is also signing a young pitcher to a contract before he reaches free agency; that’s rather a different thing.)

Lottery tickets are exactly what they sound like, the rare and lucky occasions when a team signs a pitcher with low—or no—expectations and ends up with a performance beyond their highest hopes.

One of the great pitching lottery tickets was purchased by the Chicago White Sox in the form Esteban Loaiza before the 2003 season. Coming off two seasons in Toronto in which he posted a collective 20-21 record with a hideous 5.33 ERA, Loaiza signed with Chicago for just $500,000. The right-hander responded with the best season of his career, winning 21 games with a 2.90 ERA, a performance good enough to earn him both a start in the All-Star Game and second place in the Cy Young voting.

Bargain or Bust? For Derek Lowe, it depends on the contract. (Icon/SMI)

Two years later, the New York Yankees—having signed notable busts Carl Pavano and Jaret Wright for nearly $75 million in collective dollars in the off-season—hit the pitching lottery with Aaron Small. A career minor leaguer with fewer than 220 career innings, Small signed a minor league contract with the Yankees for an amount described as being in “the five-figure range” before the 2005 season. By the end of that year, Small had won 10 games without a single loss and helped drive the team to October.

These lottery tickets are nice—as a Yankee fan I still have many fond memories of Small—but are rarely effective past the one-year wonder stage. Indeed, neither Loaiza nor Small would finish the next season with the team where he had his greatest success.

Strong pitching investments on the other hand, are those contracts awarded for big dollars with big expectations. As my Annual column proves, these contracts end up as mistakes with alarming frequency. But there are some notable successes.

The first name on this list is Randy Johnson, who signed his four-year deal worth $52.4 million with the Diamondbacks on this day in 1998. The contract made Johnson one of the highest paid players in baseball—during the four years of the deal he ranked between second and fifth in salary—but Johnson was worth every cent.

In fact, that understates how great Johnson was those four years. The simplest way of explaining his greatness is pointing out that he won the Cy Young Award all four years, totaling 104 of the 128 first place votes in that period, including 62 of 64 in 2000-2001.

On the whole, Johnson went 81-27—an average of more than 20 wins a year—with a 2.48 ERA (188 ERA+) over 1,030 innings. It is a stretch of pitching that compares favorably to any four-year run in baseball history.

Exactly a year later, Mike Mussina would sign a contract with the New York Yankees which, while not matching Johnson for outstanding quality, would deliver in its own right. Signing in the Bronx for six-years and $88.5 million—the same off-season when Mike Hampton and Denny Neagle would sign their laughable contracts with the Rockies—Mussina would give the Yankees 92 wins over the contract’s life.

That was owing to more then just the strong Yankee teams behind him; Mussina delivered a 3.80 ERA (117 ERA+) in 1200 innings. Only Johnson, Curt Schilling, Roy Oswalt and Barry Zito had a higher WAR than Mussina with as many innings in that span.

Moreover, while the Yankees failed to win a title during Mussina’s time with the team, it was largely because of failings elsewhere than the “Moose.” In the 2001 playoffs Mussina threw 24 innings with a 2.63 ERA, including seven critical shutout innings with the Yankees facing elimination in Game Three of the ALDS. In 2003, he was even more clutch, providing three innings of shutout relief in Game Seven of the ALCS, allowing the Yankees’ famed comeback to take place.

Derek Lowe may not leap to mind in the department of solid pitching investments, especially for Braves fans who have watched the veteran righty post a worse-than-average ERA his first two seasons in Atlanta. But for the Dodgers, Lowe was a wise choice. Signing for four years and $36 million, the sinkerballer won 52 games. Even more impressively, he did so while averaging nearly 215 innings per year and posting a collective 3.59 ERA (120 ERA+) in Los Angeles.

The “R” in WAR
How a person can be a hero by being a zero.

At various times during his Dodger tenure, Lowe was out-earned by busts like Jeff Weaver, Jason Schmidt and Andruw Jones. But he simply continued to put up quality numbers, justifying his salary and winning games.

If there is one thing to be made clear from comparing the list of pitching successes to those of failures, it is that a long-term contract for a pitcher is rarely a good idea. That does not stop teams, of course, who have in the past few seasons shelled out big money for successes like CC Sabathia and Roy Halladay, as well as failures like the Atlanta version of Derek Lowe and John Lackey. Nonetheless, because it is the successes of pitchers like Johnson which stand out in memory, it seems like these long-term contracts will continue to appear.

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I think you are being a little hard on John Lackey after all if he wins the Cy Young next year the contract won’t be a bust.


How about the Pedro Martinez contract with the Red Sox, Greg Maddux’s first Braves contract, or several of Roger Clemens’ contracts?

Richard Barbieri
Richard Barbieri

Like I said, I was just going for contracts signed in the last decade or so. All of those you list are excellent choices going a little farther in the past.