What the Hell Were You Thinking? Todd Helton Edition

*Over the next couple of weeks, Jorge Says No! will take an in depth look at some of the worst contracts in baseball. We'll evaluate why the player was signed, what went wrong, and future implications of the contract. Behind every bone head decision, there has to be a reason for it...right?*

There was a point in Todd Helton's career where it seemed as though he could do anything. Helton was a gold glove first baseman and a dynamic hitter who could hit for both power and a very high batting average. He was the face of the franchise for the Rockies, who were very eager to reward Helton for his production and commitment to the Rockies.

Why Sign Helton: Even though this extension did not kick in until 2003, the Rockies gave Helton his extension before the 2001 season. Helton, then 27, was coming off a season in which he hit a staggering .372 with 42 home runs and 147 RBI. These amazing statistics cemented Helton as one of the best hitters in baseball and left the Rockies salivating to lock up their biggest star. The Rockies gave Helton a nine year extension worth a breath taking $141 million bucks.

At only 27 years old, the Rockies thought they were locking up their franchise player for the next decade. This is a quite a feat for the Rockies, who often struggle to spend big money and lure big free agents to the thin air of Colorado.

What Went Wrong: The amazing aspect of this contract is that Helton continued to perform at an optimal level for the first two years of the contract. However, beginning in 2005, Helton began to gradually decline in part because of injuries and age. All of a sudden, Helton seemed to be sapped of his once mighty power and the ridiculously high batting average starting to come back down to earth.

I blame the Rockies for this one. The nine year extension kicked in when Helton was 29 years old, which meant that the Rockies were not likely to get Helton during his prime. Instead, the Rockies would likely watch their franchise player decline with age as they continued to pay him an absurd amount of money, which is exactly what happened.

Helton just became older and frail, which the Rockies should have expected. Instead of preparing for the inevitable, the Rockies made Helton one of the highest paid players in baseball.

Future Implications: Helton is no longer the player he once was, even though he is still quite productive. He can still hit for a high average and get on base with the best of them, even if he can no longer hit more than 20 home runs. If Helton can stay healthy, he can still be a useful player and help the Rockies win games in 2009 and beyond.

However, there is no way to get around how badly this contract has and will turn out for the Rockies. The Rockies only have roughly a $55-$70 million dollar payroll, but Helton takes up roughly 20-25% of that. It will be very difficult for the Rockies to compete if Helton is incapable of performing at a high level.

Also, if Helton was not signed to such a long and consuming contract, then the Rockies probably would have been able to make a stronger run at re-signing Matt Holliday instead of trading him to the Oakland Athletics. Holliday could have been the new face of Rockies and have made the Rockies a much stronger team in 2009 and beyond, but because of payroll constraints, the Rockies were forced to move him.

Furthermore, Helton's contract will prevent the Rockies from adding any substantial pieces that could help them compete in both the long and short term. With Helton signed through at least 2011, the Rockies will probably be forced to remain inactive in the free agent market.

It's unfortunate for the Rockies to be burdened with such a consuming contract because I really think that they could have built something special.

Lesson Learned: Sign players to long term extensions during their PRIME only. The Rockies will likely only get two great seasons from Helton out of the nine year contract, which is not totally surprising considering his age.

Also, nine year deals in general are just a bad idea. Unless the player is only 24 or 25 years old, nine years is a long time for a team to be burdened down by the demands of one player's exorbitant salary.