Why The Pirates Should Be In Win-Now Mode (Kind Of)

Michael McKenry of the Pittsburgh Pirates high fives teammates before walking into the dugout before the game against the New York Mets on June 13, 2011 at PNC Park in Pittsburgh, Pennsylvania. McKenry was added to the Pirates roster last night. (Photo by Jared Wickerham/Getty Images)

The Pittsburgh Pirates are not going to win the World Series this year. I hate to spoil things, but I have a pretty good feeling about this one. Also, Bruce Willis is dead the whole time.

But The Pittsburgh Pirates should consider making minor trades and tweaks as if they were going to the World Series. They should actively pursue in-season upgrades to patch lineup holes, parting with decent-but-not-great prospects to do it.

Those two things aren’t mutually exclusive. I used to think they were. A team that doesn’t have a good chance to contend shouldn’t be making trades for the short term -- they should be socking away prospects great and small, sifting through the rubble, trying to figure out what’s pyrite and what’s gold. The Pirates are just five games back in the NL Central entering Tuesday, but there probably aren’t a whole lot of people in the organization who think the team is in win-now mode.

But if the cliché is that flags fly forever, there should be some sort of corollary for a team that hasn’t been over .500 in 18 seasons. It’s a special circumstance. The Pirates won’t get a flag for finishing over .500, but they’d avoid another patch on the quilt of shame. That’s kind of like a flag. And it’s a great reason for the Pirates to upgrade mid-season as if they were gunning for a division title.

This isn’t to suggest that the Pirates should trade a Carlos Santana for a Casey Blake just to finish .500. But they shouldn’t be scared to make a move, to upgrade at first or short if the right deal presents itself, even if that deal isn’t one that’s necessarily going to help the team in 2012. I don’t want to pretend like I know what it’s like to follow a team that hasn’t finished over .500 for a couple of decades -- though I have a pretty good idea -- I’d wager that a winning season for Pirates fans would feel pretty sweet. There’d be a sense of accomplishment and anticipation that would push the franchise forward more than the difference between the #11 pick and the #14 pick.

There’s a core in place with Andrew McCutchen and Pedro Alvarez, and there are reinforcements coming with Jameson Tallion, Gerrit Cole, and Tony Sanchez. The Pirates have accumulated enough talent to where they will have a tough time falling into a bunch of top-five picks again. If there's to be a winning Pirates team in the near future, these are the players who will be a part of it. And a little help in the short-term to help them in the present? It's not a bad idea.

So in conclusion, if another team offers the Pirates legitimate prospects for Kevin Correia or Paul Maholm, they should take the deal because not doing so would be completely negligent, short-sighted, and silly.

Wait, that's not the right conclusion.  Heck, I don't know. I'm just glad I'm not Neal Huntington. Franchises at a crossroads are so weird.

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