There might not be a better time to buy on Justin Upton. Mandatory Credit: Mark J. Rebilas-US PRESSWIRE

Justin Upton, Carlos Quentin, And The Upstart Pittsburgh Pirates

It’s been a very long time since the Pittsburgh Pirates were in serious playoff contention, but now that the long-suffering franchise finds itself leading the National League central at the All-Star break it may be time to bolster the roster. To honestly compete with the Reds and Cardinals for the remainder of the season, the Pirates probably need to make multiple upgrades, but the offense has to be considered the area most in need of assistance. Only five teams in all of Major League baseball have scored fewer runs than the Pirates, so it makes sense that we’re hearing rumors that the team is interested in names such as Justin Upton and Carlos Quentin.

With so much homegrown talent still on the way, does it make sense for the Pirates to gamble on a playoff spot now?  Within the last half-decade we don’t have to look past Pittsburgh’s own division to remember the Brewers gutting their farm system to put an end to their years of suffering. While the Brewers made the playoffs as a result of their acquisition of CC Sabathia, the Milwaukee franchise was left with few ways to help itself and now faces another potential rebuilding phase. It may be risky for the Pirates to potentially halt their era of homegrown dominance before it even has a chance to begin.

If the Pirates do decide they want to gamble on their 2012 squad, it would make sense to do so on a player who could also help future teams rather than a half-season rental. The two names primarily mentioned as potential Pirate gains are Justin Upton and Carlos Quentin. While Quentin can hit, he’s five years older than Upton and has a lower ceiling. Quentin is what he is; Upton still has the talent, and even a couple of seasons on his resume at the tender age of 24, to suggest he could still be one of the best players in the game. Upton is also not likely to ever carry as small a price tag as he will right now. He’s in the middle of the worst season of his young career and his team is openly discussing that they will listen to offers for him.

Regardless of which outfielder the Pirates decide to target, they will need to put together a pretty appetizing prospect package. The Pirates have an abundance of pitching prospects littering their system and fewer capable young hitters, so maybe dealing for someone like Upton, who is signed at an affordable price through 2015, would actually make sense. Obviously netting Upton would cost Pittsburgh more than getting Quentin, but how much more? Both the Diamondbacks and Padres are said to be seeking top-notch prospects rather than a collection of mid-tier options, so names like Jameson Taillon and Gerrit Cole are likely to come up even if the Pirates aren’t willing to part with them.

I don’t actually think the Pirates will be willing to complete the package necessary to acquire Upton, and they probably won’t be able to satisfy the Padres to pick up Quentin either. While this might be disappointing for some Pittsburgh fans, it would be the right move. The Pirates have names on the horizon who will be able to help the horizon at a fraction of the cost, thus freeing up budget room to add free agents where it’s necessary. The very best choice for the Pirates, who by all advanced metrics have been outplayed by the Reds and Cardinals despite raw record, is to stand pat and let things mature naturally. Being a stick in the mud is not easy or fun, but someone has to do it!

If Brian’s writing strikes your fancy, read his work at StanGraphs and follow him on Twitter at @vaughanbasepct.

Tags: Arizona Diamondbacks Carlos Quentin Gerrit Cole Jameson Taillon Justin Upton MLB Trade Deadline MLB Trade Rumors Pittsburgh Pirates San Diego Padres

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