With nine days to go before the July 31 non-waiver Trade Deadline, this is a fascinating quandary for the team and its lead baseball executive. Huntington has the chips to go all-in -- by all accounts, the Bucs have a disproportionate three among MLB.com's top 50 prospects -- but doing so comes with the risk of still falling short while weakening the future. Yet he absolutely cannot afford to be passive and see it all fall apart again.
There are other factors to consider, too. There are players who wish to retain clubhouse chemistry yet also expect the front office to provide needed help, and there is a fan base starved for a winner. Yet there also is a need to foster long-term success.
On the other hand, the Pirates have big days directly ahead of them, beginning with a five-game series against the first-place Cardinals beginning next Monday at PNC Park.
Huntington suggested that GMs with whom he has talked trade are preying on Pittsburgh's predicament in attempts to drive up the price.
"We've been reminded a couple of times that we're in a unique circumstance of not only trying to break the streak [of 20 straight losing seasons] but trying to get to the playoffs," Huntington said. "This is a very good club. How can we add to it? Certainly there are areas we can improve, but it's not a desperation situation. We don't have desperate weaknesses.
"We've been in good spots the last couple of summers, and if we stay motivated and we do what we can off the field, we'll look up in September and October and still be in a good spot. This is a club we believe in, and we want to do what we can to help it get better, to take that next step."
That next step clearly is into the postseason. The route there, the regular season, is the proverbial marathon, and the Trade Deadline has been the Bucs' Heartbreak Hill the past two seasons.
How do they get over it?
The Pirates' top need is obvious. Aside from perhaps bolstering other areas -- bench, rotation, even the lights-out bullpen -- Huntington's main target is a right-handed power hitter who plays right field. Not so much because right field, contrary to what has been said and written, is such a black hole in the team's lineup, but because it is the one position where the Bucs have room for growth. Garrett Jones and Gaby Sanchez would then became part of a bona fide platoon at first base.
But relatively few available players fit the profile. Alex Rios of the White Sox headlines the list, the Mets' Marlon Byrd is a leading fallback option and a surprising possibility could be Ryan Doumit, the former Bucs catcher who has reinvented himself as a full-time outfielder with the Twins.
Huntington might also get a do-over on Hunter Pence. He declined a year ago to pay the Phillies' asking price for Pence and watched him instead go to the World Series with the Giants, who now may put him back on the market if they continue to sit below .500.
Huntington is at the dickering stage. He has been a Deadline doer, for good reason.
"If you want to move early, you need to pay more," Huntington said. "Clubs are hoping to find that one desperate club that will overpay."
The jewels of the farm system may still be off-limits, with the possible exception of Alen Hanson, whose problems on defense may suggest he may never cut it at shortstop. Gregory Polanco is potentially a long-term answer in right but could be pried away for an immediate solution. Highly regarded right-hander Jameson Taillon is a keeper, while the current rotation includes three veterans -- A.J. Burnett, Wandy Rodriguez and Francisco Liriano -- who might not be with the team in two years.
Beyond those three, Huntington can deal from organizational depth.
"But just because we have a deep system doesn't mean we're any more willing to overpay. It still needs to make sense for us," Huntington said. "It does, however, allow you to make moves with the confidence that you're not depleting the farm system. But there are many examples of clubs pushing too hard for today at the expense of tomorrow. We have to be cognizant of that.
"At the same time, the fan base has been patient a long time -- and we have to be cognizant of that, too. We want to do what we can to help this club get better, and take that next step."
It would be one thing if Huntington had spent the prior two Trade Deadlines sitting on his hands, then watched the club fade. It's been quite the opposite, as he engineered a total of six deals -- only to watch the moves backfire in a cumulative post-Deadline record of 38-77 over those two seasons.
Huntington took a different route each time. In 2011, he dealt for so-called "rentals" Derrek Lee and Ryan Ludwick, veterans who were headed for free agency, and last year, he acquired younger players, Sanchez and Travis Snider, who were still under club control.
Obviously, Huntington can't be guided by those past experiences. They're too varied.
"We've never gone in with a premeditated view on rentals, whether we want or don't want them," Huntington said. "We've gone into the Deadline to impact that year's club as best we could. Now, while it does not make a ton of sense for us to give up an elite prospect for a two-month rental, you've always got to have the majority of attention on today.
"I don't know that what we did in the past will impact what we do this year. I do hope to get better at this job every day I do it."
Interestingly, in trying to help the Pirates close the deal and make the playoffs, Huntington may also be attempting to finish his own deal. The subject of considerable past criticism is a front-runner for Executive of the Year, with his offseason acquisitions -- Mark Melancon, Russell Martin and Liriano, among others -- critical to the team's first-half performance.
By adding to his resume, Huntington will attempt to put into manager Clint Hurdle's hands the tools to uncover that booty.