Pay for the Past or Let Go for the Future? The Derek Jeter Debate

            Derek Jeter as a baseball player is like an 11-year old dog. He’s starting to go blind in one eye. His fur is starting to get a little patchy in spots. He doesn’t chase after toys the way he used to. However, he still holds the same standing with the family he’s always had. This sums up the dilemma for the New York Yankees as they try to sign him. (EDITOR'S NOTE: This analogy only applies to Jeter the ball player. Jeter is one of the coolest dudes to ever play sports. His performance on Saturday Night Live in 2001 sealed the deal for me. Check out a list of his past girlfriends, which reseals it) 

            For the first time in his career, Derek Jeter is a free agent. He’s coming off a season where he posted his lowest batting average, fewest home runs, and worst on-base percentage of his career. Jeter’s range at short-stop is also dwindling with each passing season (don’t let the ridiculous Gold Glove award he just won fool you. Jeter is a stiff in the field). There’s a very real possibility that Jeter will be forced to change positions, which he is hesitant to do. Amazingly enough, the Yankees have offered him a contract worth $63 million over the next three seasons. What’s even more stunning is that Jeter has refused this offer and is holding out for a four or five year deal.

            This is a very fascinating situation. I’m not sure if there’s necessarily a right answer in the short-term no matter how the Yankees play it. Sign him, and get ridiculed for devoting so much money to a player that appears to be in decline. Let him go, and get heat for not keeping one of the five greatest Yankees of all time. Knowing that there is no short-term win, let’s look at all the factors that will come into play.


Q: Do the Yankees need Jeter more than Jeter needs them?

A: You’ll be hard pressed to find another team that would offer Jeter $21 million a year. To be honest, there wouldn’t be a team that would offer him more than $10 million. Jeter has no leverage if the Yankees want to play hardball.

Q: What are the odds that Jeter will be in decline for the rest of his career?

A: Hard to say. Jeter’s numbers in home runs and stolen bases have been erratic for his entire career, so you can’t point to those numbers as indicators of whether or not he’s fading. The scary number is his batting average. His lowest average in a season before 2010 was .291, and he had 11 seasons hitting over .300. Is it realistic to expect him to train hard in the winter and come back with a vengeance in 2011? I don’t see it happening (especially with his marriage to Minka Kelly. Jeter was in the discussion of greatest bachelor of the past 15 years. He’s second to George Clooney in my book. Maybe Jeter tying the knot is the most telling sign that he’s moving out of his prime. Not that I would complain about being married to Minka Kelly. Moving forward…).

            His declining defense can’t be overstated either. Unfortunately, they don’t have a good place to move him. First Base would be the perfect candidate, but do you want to have a guy at 1^st that hits .265 with 12 home runs? And pay him $21 million? First is moot anyway because of Mark Teixeira. Outfield would make some sense, but teaching a 37-year old to play left field would more than likely be a disaster. The DH spot will already be clogged by some combination of Jorge Posada and Alex Rodriguez.

Q: Who could replace Jeter?

A:  A stiff. There are not a lot of shortstops on the free agent list. World Series hero Juan Uribe would be the most interesting option, but I’m not sure if his World Series performance would carry over to a full season in the Bronx. One option that has been floated is swapping Robinson Cano over to short, which would make Orlando Hudson an option for second. The Yankees have no viable replacement in their minor league system.

Q: Does overpaying Derek Jeter really matter to the Yankees?

A: Not really. This team is made of money. They could give Jeter $600 million for 3 years, and still have money to sign Cliff Lee and Carl Crawford.

           I fully expect Jeter to eventually sign the three-year deal for $63 million. There might be some messiness as Jeter lobbies for a 4-year deal (leading to wall-to-wall coverage by ESPN causing Tim Kurkjian’s voice hitting an octave level only heard by small dogs), but Jeter realistically can’t complain too much. It will be quite comical to watch the Yankees in 2013 when half their roster is eligible for an over-40 softball league. As a Red Sox fan, I can’t wait.