First and foremost: I just realized Howard's contract hasn't even kicked in yet, so it's pretty much irrelevant here anyway. He's still on the 3 year deal they gave him in 2009. What would have happened if they decided not to extend him (in other words, he'd be an impending free agent) and then signed the much-better Prince Fielder this offseason instead? Would they not be in a better position to win?
But in any case, assuming this year was part of that massive extension... yeah, flags fly forever, I get that. But that doesn't suddenly justify handing out $100M+ to the most overrated first baseman in baseball when he isn't nearly worth it. And it does matter for the future of the team; I'm sure they'll enjoy him eating up $20 to $25M annually through 2016 or 2017. Considering where he is now, it might be really ugly.
It just seems wrong to say "it doesn't really matter" how much a team severely overpaid a player because he helped them win a World Series. It seems like such a scapegoat to the fact it's a bad contract. I think it's also unfair to ignore the potentials if they decided to, say, go with a much cheaper first baseman who was nearly as valuable as Howard (not hard to do, actually) and spend that extra money on other areas to improve the team even more, or, as I mentioned above, signed the superior Prince Fielder instead this offseason. Maybe they would win 3 World Series instead of just 1. Not to mention, we're talking as if the Phillies have already won it. They may be the favorites, and I picked them, but they do have to play the games.
And while winning the World Series may be #1 under a team's goals, creating surplus value and setting your team up for the future should be right under it. They kind of lead into each other too; if you accomplish the latter, you should receive many chances at accomplishing the former. If the Phillies don't end up winning anything in the next few years and continue to dump prospects at will, they will have accomplished none of those.
Edited by nmigliore, 02 October 2011 - 10:27 AM.