It was yet another losing season for the Pirates, but at least they displayed some reasons to believe things would start getting better soon. Sure, it was just one star and sure he stood alone in a lineup of virtual nothingness, but he was on the cusp of his prime and there were prospects on the way, including a no. 1 overall pick on the mound. So things were looking up on the Pirate Ship despite a brutal finish to an otherwise promising year. This streak of losing seasons had to come to an end sometime in the not-too-distant future.

Anyone who has been following baseball closely knows the story. But do you know the year?

The year was 1998. Sounds more recent than that, right? The player was Jason Kendall—an up-the-middle star—and don't lose sight of that in the myopia of his sad career denouement—in his 20s. The no. 1 pick, by the way, was Kris Benson.

The analogy is obvious to state, but it shouldn't be taken as a predictor of future peril. Just because the Pirates went nowhere after that ’98 squad doesn't mean a thing for Andrew McCutchen's team heading into 2013 and the streak beyond its current 20 years of losing-ness.

What it does illustrate is the potential for and one example of a team wasting its star's prime, which the Pirates are in danger of doing with McCutchen. The now 26-year-old outfielder stood alone in the batting order among a squad of disappointments, unproven talents and Quadruple-A types, compiling 4.9 wins above replacement player while none of his teammates poked their heads above 2.

In fact, McCutchen is the only player since BP’s WARP data originates in 1950 to be his team's only hitter over 2 WARP in three consecutive years. Or any three years, for that matter.

There are three ways for the Pirates to go about remedying this situation amid the backdrop of some pitching prospects on the way (though none slated to arrive imminently) and few elite bats in the system.

1. They could trade him.
Switching tenses for a minute, they could have traded him, and this is precisely what previous Pirates management teams would have done. It would be a very Pirates move to adjust the winning timeframe into the future. The club once traded the most productive offensive outfield in the National League—Jason Bay, Nate McLouth, and Xavier Nady—in 10 months, including two of them in a week.

The time to trade McCutchen, if the team was going to do it, was after the 2011 season, when the free agent outfield class was Carlos Beltran and a bunch of debris.

There would have been a mutiny among what remains of the fan base, though, and they didn't trade him. In fact, they extended him during spring training of the following season, locking him up in March 2012 to a six-year deal that covered his last pre-arbitration year, all of his arbitration time, and two years of free agency.

Still, the Pirates could trade him and try to acquire the hitters to partner with Gerrit Cole, Jameson Taillon, and Luis Heredia or the pitchers to build what could be one of the game's best rotations when they all mature. (Their best position prospect, Gregory Polanco, plays the same position, as did Starling Marte.)

The Pirates pursued this trade-later approach with Kendall after his rich extension, selling off his three most expensive years to the Athletics but getting little in return because it was no longer a favorable contract.

McCutchen's deal, on the other hand, is incredibly team-friendly and would give him trade value unseen among any player dealt in recent memory if the Pirates try to adjust their competitive window once again. 

2. They could seriously build around him.
More pleasing to the Pirates fan would certainly be option no. 2, which accelerates the timeframe of winning—or at least desired winning—ahead of that of their top prospects.

Faced with a similar situation with Matt Kemp, who stood alone in a bad lineup in 2011, this is what the Dodgers did, albeit with a payroll in an entirely different class. Kemp had the highest WARP of any player who was his team's only two-win position player since modern free agency began in 1975. Kendall in 1998 was second. McCutchen in 2012 was seventh, isolated as he'd been the two years prior.

The Pirates stayed tight, though, limiting their payroll to what could be the second lowest in the NL ahead of only the Marlins’. Their two big pitching acquisitions of the last two years, A.J. Burnett and Wandy Rodriguez, landed in Pittsburgh only because the trading team was willing to eat a large portion of their contracts. Their addition of Russell Martin this offseason came with a financial counterbalance, the trade of closer Joel Hanrahan (and the corresponding creation of a closer void).

Yes, they are a smaller-market team than the Dodgers, but so is the team just up the road in Cleveland, which decided to go for it despite lousy attendance and recent results.

3. They could make individual moves each for their own sake with no big-picture motive.
Ultimately, they've taken neither of the first two paths. This is what they've done, and most of the moves they've made have been solid, which is why it’s hard to criticize any of them taken individually. Martin is due for a BABIP bounceback from the lowest figure of his career (.211), which should keep him offensively productive even in a more difficult home run park, and he is an underrated defensive player. Burnett worked out nicely, and Rodriguez did too. And far be it from anybody here to criticize cashing out early on a closer, one of the game's most replaceable commodities.

But these moves pay little heed to the larger picture of the franchise, with a winning lottery ticket of an asset getting a year older and more expensive. McCutchen will get raises of $2.75 million after this year, $2.75 million after next year, and $3 million the year after that. At the same time, the last class that was supposed to be his complement on the streak-breaking Pirates team—Pedro Alvarez et al—will be getting more expensive or will have to be replaced in the free agent market for more money. Meanwhile, the contracts of pitchers being paid largely by other teams will expire, and it will be time for the Pirates to spend for themselves on the rest of their rotation beyond the prospects.

Statistically, there appears to be no improvement in sight. The Pirates won 79 games last year as their true talent level finally exposed itself in a jerky path to a .488 winning percentage. Their PECOTA projection for 2013, fittingly, has them at exactly 79 wins—tied with the Brewers for third/fourth in the NL Central.

In the division that will likely prove easiest to win over the length of McCutchen's great contract, the Pirates are in danger of letting that confluence of opportunities pass them by.

A version of this story originally appeared on ESPN Insider Insider.

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I feel like as long as the PIrates don't re-sign Randall Simon, their fans will be happier.
At least one sausage in Milwaukee will be.
They could try to extend him.
No big-picture motive? Seems to me everything they've done since they drafted Pedro is to put a competitive team on the field for 2014 and beyond. Spending more on the draft than any other team, being extremely active in the International market and resigning a superstar for the first time in God-knows how long. With the big picture focused on 2014/2015, they continue to bring in mid-to-slightly-below-mid-level free agents to make the team as competitive as they can be right now, without risking any of the future. These include Burnett, Wandy, Martin, Gaby, etc. So unless I misunderstood (which could have happened, I only skimmed the article), I just don't see where they are lacking in big-picture strategics.
As a long suffering Pirates fan, I have seen option 1 way too many times. No way can they trade McCuthen until they reach 82 wins.

The biggest issue is that ownership won't commit to spending on the major league roster until more fans show up at the park. That would be like General Motors saying that their vehicles are below average but if you buy one now they will improve the quality in the future.
Is close-to-.500 really that bad of a spot for the Pirates to be in right now? I mean, just putting in a winning season would be huge at this point.
Why spend on the big league roster yet? I don't see a reason to until some of the investments start paying off that they've made via the draft. I don't think we'll be as hesitant to bring in a decent FA or make a trade deadline acquisition once Cole, Taillon, Polanco, Hansen, Bell, Heredia, etc start making an impact in the big leagues. Or at least the first two I mentioned. Attendance has been tremendous for a team that has only spent $40-50M on it's entire roster. I think the fact that they've gone from $40 to $70M in a 2-3 year span proves that we're willing to spend once the investments pay off. Do you really think we'd have gone after Wandy, Martin, etc in 2002? No, we would have signed Matt Lawton or Kenny Lofton. We certainly wouldn't have extended McCutchen through his prime. I think it's a great time to a Bucco fan, and if our fanbase would take a second to realize the difference between right now and when Littlefield was here - they might not be such pessimistic complainers.
Seems to me that teams that trade away quality for future do quite poorly with only a few exceptions. Has BP ever looked at that. It might make sense to a businessman to trade his best player for a bunch of prospects, but it angers the fans and often fails. Before free agency, good players often stayed on bad teams and garnered the affection of the fan base even as the team lost. Those days are gone, but if a player is performing, is a model citizen and the fans like him, why not keep him instead of betting on the flavor of the month?
"Closer void"? Grilli will have them saying "Hanra-who?"
Dave - look at the deal Texas got for Teixiera. It'll boggle your mind, lol. Obviously betting on prospects is a gamble, but the team gets the immediate benefit of salary relief. Also, a lot of those types of deals are done just prior to the player leaving town without the team getting a thing in return. So while 3 or 4 prospects is a gamble, it's often better than losing the player and having nothing to show for it. With that said, the Buccos are not in a position to benefit even in the slightest by trading McCutchen now that he's locked up through his prime. I'm just talking more in general than anything the Buccos should consider.
I do think a trade of AJ to a contender at the deadline would make sure if we were clearly out of wildcard contention. I don't think we will be, but it's definitely something we should consider should we find ourselves in the position.
Why comment on an article you admittedly stated you didnt read?
"The club once traded the most productive offensive outfield in the National League—Jason Bay, Nate McLouth, and Xavier Nady"

Those were different circumstances. Only Bay, though injured, was a star and the Pirates had no minor league depth and little major league talent. They only had one starter (Maholm) with an ERA less than 4.50(!). Nady and Bay were also turning 30 and there were doubts McLouth could repeat his performance (which he never did). Also, if I remember right, the new ownership just came in. Why not trade parts, especially people like Nady, at the top of their value, to rebuild?