Roy Halladay: The Albatross to Come

Very little talk has come up about the wisdom of not only trading 4-5 top prospects for Roy Halladay, but also giving him a rumored four year, 100 million dollar contract.

What is the track record for giving a pitcher a long-term, high-dollar contract? I looked at all pitcher contracts from 1992 to 2009 that were for at least 4 years, and resulted in a contract that placed the pitcher in the top 25 in all of baseball.
All the contracts will be judged as -
Worth every cent
Decent deal for all
Not worth the money
Highway robbery

1992: Roger Clemens - 4 years, 21.25 million.
57-39 in the four years of the contract. His '92 salary was the fourth highest in baseball, so he certainly didn't perform up to the contract, though not a complete loss.
Verdict: Not worth the money

1997: Greg Maddux - 5 years, 57.5 million (highest paid in baseball history)
Definitely worked out well for the Braves - 89-45 in five seasons.
Verdict: Worth every cent

1997: Pedro Martinez - 7 years, 92 million.
Another good deal, but remember, Pedro was 26 when he signed the contract!
Verdict: Worth every cent

1998: Kevin Brown, 7 years, 15 million a year (highest in baseball at the time)
Made just 96 starts over the last five seasons of the deal. Won only 68 games in the seven years, or $1.54 million a win!
Verdict: Highway robbery

1999: Randy Johnson - 4 years, 53 million.
As good as it gets. Four years, four Cy Young Awards.
Verdict: Worth every cent

2000: Mike Mussina - 6 years, 88.5 million.
Went 78-53 over the course of the deal. Not bad.
Verdict: Decent deal for all

2001: Chan Ho Park - 5 years, 65 million.
Went 22-24 with Texas, with his LOWEST ERA being 5.46. Yes, that is $2.95 million per win.
Verdict: Highway robbery

2001: Darren Dreifort - 5 years, 55 million.
9-15 before entering the witness protection program. A whopping $6.1 million per win. Give Scott Boras credit for this one - remember Dreifort wasn't even eligible for free agency yet.
Verdict: Highway robbery

2001: Mike Hampton: 8 years, 15.1 million a year (121 million total).
Has gone 53-48 in the first seven years, or 2.28 million per win!
Verdict: Highway robbery

2004: Bartolo Colon - 4 years, 51 million
46-34 with the Angels, but only 7 wins in the last two seasons. A relative bargain at $1.1 million per win. The Angels paid $26 million over the last two seasons for a pitcher that won 15 less games than Steve Trachsel!
Verdict: Not worth the money

2007:  Barry Zito - 7 years, 126 million

Obviously, it is early on with this one, but I think we can all agree where this is going.  An ERA+ of 98, 85, and 92 in his first three years of the deal isn't encouraging.  To put it another way, Zito's contract made him the third highest paid pitcher in all of baseball, but his ERA placed him 78th!

Verdict:  Highway Robbery

The count:
Worth every cent - 3
Decent deal for all - 1
Not worth the money - 2
Highway robbery - 5

So there have been 11 high-dollar, long-term deals for pitchers in the least seventeen years. 46% of those deals were horrible for the clubs involved.  

  Long-term contracts for pitchers - just say no.