Dealing for Justin Upton

As John pointed out yesterday, the Pirates are in hot pursuit of many of the best trade targets including but not limited to Justin Upton.  The most recent news seemed to suggest that things on that front may have cooled a bit with the team unwilling to offer one of Gerrit Cole or Jameson Taillon.  Obviously we only have news reports from various MLB sources to go off of and nothing straight from Neal Huntington’s mouth so I’m not going to try and assume what he was/is thinking.  Things may have cooled or maybe they are just heating up.  There are still two weeks until the deadline so tons can happen.

But if he does/did think he is/was going to get an elite talent like Upton at age 24 with three more years of an affordable contract without bowling the Diamondbacks over, then I think he is mistaken.  Sure, the Diamondbacks have picked the absolute worst time to try and deal Upton, but I think GM Kevin Towers is smart enough to know that he can still request a mint even in a down year.  There isn’t a combination of Pirates prospects that equals a mint without including one of the blue chip arms.

Those being Cole and Taillon, of course.  Luis Heredia is probably seen as a blue chip arm for some orgs, but at 17 years old he is light years away in baseball time and not what an on-the-cusp contender like Arizona is going to want back as a highlight for their star rightfielder.  I think a deal has to start with Starling Marte and one of the potential aces and then go from there.  If that is the foundation, the “go from there” shouldn’t be too hefty, maybe a flier grade C prospect or two, but I can’t see Towers accepting Marte and a grab bag.

Obviously the Pirates are wise to offer that Marte-led package first and take Arizona’s temperature, but they shouldn’t be unwilling to include one of the arms if (when) Towers pushes back.  The Pirates organization, top to bottom, is in the best shape it’s been in for decades.  Even with Mark Appel passing, the system is still brimming with plenty of potential.  But it is just that, potential.

I’m not sure that Huntington & Co.’s dreams of this season envisioned a one-game deficit in mid-July.  Sure, they were a game out last July 16^th at 48-44, but it just felt flimsy, especially by comparison to this year.  The pitching was way over its head and the offense was little more than Andrew McCutchen.  Flash forward a year and they are 49-39 and their chief competitor just lost their best player, perhaps the best pure hitter in the entire National League, Joey Votto to knee surgery for a month-plus.

Their rotation is revamped with bat-missing arms paired with even better control than we saw last year.  And while the offense remains Cutch-led, the supporting cast is offering a lot more of late.  In short, they are legitimate contenders.  I think even the most optimistic of fans knew that they weren’t very sturdy last year and the front office certainly did which is why they made just modest deadline moves.  Plus the competition was fierce and plentiful.

I wouldn’t discount the competition this year, but this iteration of the Pirates is definitely on the level of Cincy, St. Louis and Milwaukee (who I would remove from consideration if they moved Zack Greinke).  OK, enough exposition.  In short, 2012 is different and this team is a real contender.  Back to Upton.  The reasons a deal for him makes sense are plentiful.

TIME

As I mentioned, Upton is 24 years old and signed through 2015.  This isn’t a rental you’re buying for 2-2.5 months.  He is insanely talented with a very real chance to be one of the true elite, this year’s struggles be damned.  I realize it is easy to be heavily influenced by the most recent events, but let’s not discount all of the previous ones at the same time.

Upton was one of three players to post a 119 OPS+ or better in 2,400+ PA through age 23.  The other two?  Alex Rodriguez and Ken Griffey Jr.  Include his performance this year and he’s just 1 of 8 to post a 116 OPS+ or better in 2,700+ PA through age 24.  Joining Upton and the two former Mariners are Miguel Cabrera, Albert Pujols, Cal Ripken Jr., Rickey Henderson and Eddie Murray.  In fairness, he is very much last in the group with his 116 (Henderson, 129), but that is still very impressive company.

With more and more players being locked into deal’s like both Upton and McCutchen are, there are fewer studs hitting the free agent market which only adds to Upton’s value especially with his affordable deal that would pay him $9.8, $14.3 and $14.5 million over the next three years.  He’ll only be 28 at the time of free agency, too, so it wouldn’t be unreasonable to entertain an extension if things went will from now until then.

RISK

Prospects are fun because everyone loves dreaming on their ceilings, but they so rarely meet their ceilings that it is almost an exercise in futility on par with dreaming on what you would spend your Powerball winnings on if your numbers came through for the jackpot.  Upton isn’t fully actualized, but he has over 650 games of getting it done in the big leagues, most of them at a star level.

Look at what the Tigers did when they acquired Miguel Cabrera in the winter of 2007 when he was going into his age 25 season.  They started with a pair of elite blue chip prospects in Cameron Maybin and Andrew Miller and then went from there.  That deal looks better by the day because neither panned out, but even if they had, it is still a deal GM Dave Dombrowski  would do over because you always play the odds of betting prospects for mid-20s actualized stars who have legitimate “once-in-a-lifetime” upside.

Sure, there is some risk on the Pirates end if they were to execute a deal for Upton.  What if he doesn’t take the steps forward that many (all?) believe he will or at least return to previously established levels while Marte becomes Austin Jackson and Cole/Taillon become a strong #2 bordering on ace-level like Matt Cain?  But that’s another what-if game that is futile and would leave you paralyzed into never making a move.  The risk in a deal like that lies predominantly with Arizona.  That is a certainty because prospects aren’t.

UPGRADE

When the Chicago White Sox stole Kevin Youkilis from the Boston last month, it was as close to a can’t miss as you can get with a trade.  Their third base production was positively god awful on every level.  Even a neutered Youkilis was going to be an upgrade over Brent Morel and an out-of-position Orlando Hudson.  In fact, even with his hot start there, they still have the worst OPS in baseball at 3B by a wide margin (.523 w/Oakland at .540).  Pittsburgh’s rightfield situation isn’t quite that dire, but it’s an obvious hole primed for a premium upgrade.

The .733 OPS from Pittsburgh RFs is 23^rd in the league.  Even a static Upton would be an incremental upgrade (.735), but obviously the expectation is that he can exceed that level with relative ease.  His .347 OBP would be a major upgrade over the ugly .299 currently patrolling right for the Pirates.  And while this move would signify that the team is absolutely serious about doing all they can to win 2012, it cannot be stressed enough that a big appeal for an Upton deal is the amount of time it has to pay full dividends (3+ years).

CONCLUSION

Given the dearth of prime hitters available on the trade market (especially after Edwin Encarnacion was signed to an extension last week), Upton is the clearest path to a major offensive upgrade with the added benefit of not being a rental like Carlos Quentin.  The price will be steep for such a prize, but steep doesn’t mean it’s wrong.   A future rotation centered around McDonald, Cole, Taillon and Heredia, but betting on three pitching prospects to reach their potential is worse than betting 00 on a roulette wheel (ask Baltimore and Kansas City).  So give Arizona that spin on the roulette wheel and grab the proven stock that is already paying a dividend with the chance for so much more.