The phrase “timing is everything” might be cliché, but when it comes to deciding to which young superstar he should offer a multiyear contract, a general manager’s timing must be impeccable, as is his organization's evaluation and projection of a player's ability.
Signing players to long-term extensions benefits the team for two obvious reasons: It can save money in the long run and it delays a player’s free-agent eligibility. It behooves any club with good, young non-arbitration eligible players with four or fewer years of service to try to sign its best players long-term. The further a player is from free agency, the lower the deal and the greater the discount.
In other words, the closer the player gets to free agency, the more difficult it is for the team to make a deal. The open market usually compels the player to simply play out the contract and see what dollars will be available to him in free agency. Yankees second baseman Robinson Cano is a year away from free agency and will command more dollars than any extension might bring him, so it makes sense for him to wait.
By the same token, an agent such as Scott Boras operates on a philosophy that revolves around taking as many of his clients as possible to free agency to maximize their return. Thus, young stars such as Eric Hosmer, Mike Moustakas and Elvis Andrus are contract extension candidates, but quite frankly a waste of their general managers’ time based on Boras' track record of representing players.
In the end, if the team can’t negotiate what they perceive is a savings from the arbitration system or can’t secure a free agent year, then they usually walk away. And for most players, free agency almost always is a win.
On the other hand, there are many other young budding stars with whom general managers would be smart to wait another year before offering a contract extension. Waiting another season allows GMs to see if players such as outfielder Bryce Harper or first baseman Anthony Rizzo make adjustments to the league’s adjustments to them, or that a career year isn’t simply a mirage, such as third baseman Chase Headley or right-hander Kris Medlen. It’s just more evidence a player will live up to his potential and lessen the risk of a multiyear deal backfiring.
There are three pitchers eligible for free agency after the 2014 season -- Justin Verlander, Felix Hernandez, and Clayton Kershaw -- who will receive most of the attention regarding contract extensions. However, here are six other players whom I think teams should try to lock up in multiyear deals before Opening Day. It is the optimum timing for their clubs to save money from the arbitration process and buy out some free-agent years.
Mike Trout | LF | Age: 21
Trout was the best and most complete rookie to make his major league debut since Barry Bonds. Despite only one year of data on him at the big league level, I’ve seen enough that I’d sign him to a 10-year deal now. Trout has all the tools and can impact the game with his bat, power, speed, glove and personality. He profiles as a leadoff hitter or as a No. 3 hitter. He hits breaking balls, changeups, fastballs at all eye levels, on the black on both sides of the plate, but can lay off any type of pitch outside the zone. He has years of accolades ahead of him so the price will only go up. Now is the most cost-effective time to tie him up for a decade, which will allow him to go into free agency at the age of 31.