When the Reds inked Jay Bruce to a six-year extension earlier this month, Rob Biertempfel of the Pittsburgh Tribune-Review took the opportunity to examine how the contract could affect Andrew McCutchen. While the Pirates have not yet discussed a multiyear extension with their center fielder, Biertempfel suggested that McCutchen's value would be similar to Bruce's.

The more appropriate comparison for McCutchen might actually be the player whose contract Bruce's appeared to be modeled after – Justin Upton and his six-year, $51.25MM extension. When Upton signed the extension last winter, he had posted a career slash line of .272/.350/.485 in 1157 plate appearances. At the time, McCutchen acknowledged his track record in the majors wasn't as strong as that of the Diamondbacks' outfielder, but after a strong 2010 season, the gap has closed. McCutchen's current .286/.365/.459 line, in 1146 plate appearances, matches up well with Upton's pre-2010 numbers. Upton exhibited a little more power (43 HR to McCutchen's 28), and played better defense, according to UZR. However, McCutchen plays the more challenging position in the outfield, and is more dangerous on the basepaths (55 SB to Upton's 23).

While Upton, Bruce, and McCutchen are all comparable talents, performance and potential aren't the only factors the Pirates will take into consideration when deciding whether to extend McCutchen. One difference between Upton's and Bruce's deals involves service time – Upton had acculumated just over two years of major league time when he inked his extension, meaning the first of the six years was a pre-arbitration season. As such, his contract covers just two free agent years, while Bruce's covers three, with a club option for the fourth.

Heading into the 2011 campaign, McCutchen has racked up one year and 123 days of service time, which poses an interesting dilemma for both the Pirates and McCutchen's representation. This fall, Bruce was among the group of players who became arbitration eligible early by achieving Super Two status; this year's cutoff was just two years and 122 days of service time. If the cutoff is similar in 2011, McCutchen could become arbitration eligible as early as 2012, which would have a significant impact on Pittsburgh's payroll going forward. Because of the uncertainty surrounding the 24-year-old's status, the two sides may choose to wait for some clarity before seriously discussing a long-term deal.

The more pressing question than the issue of service time though is whether the Pirates will even be willing to pay somewhere in the neighborhood of $50MM in a multiyear extension. Players who have roamed the Pittsburgh outfield in recent years, such as Jason Bay, Nate McLouth, and Xavier Nady, have all eventually been traded before their salaries became exorbitant.

Such an extension for McCutchen wouldn't be entirely unprecedented though. Ten years ago, the Pirates agreed to a six-year, $60MM deal with Jason Kendall, the largest contract in team history. And while they haven't committed nearly that much money to a player in recent years, the club has exhibited a willingness to spend some cash; they've committed big money on the amateur draft and, as MLBTR's transaction tracker shows, have added a handful of major league free agents this month. Perhaps, with youngsters like Pedro Alvarez, Jose Tabata, and Neil Walker now playing at the big league level, and with plenty of promising minor league talent on the way, Pittsburgh would be inclined to keep their core intact by locking up McCutchen, the relative veteran of the group.

For now, the bet here is that the Pirates wait to verify whether or not McCutchen will become a Super Two. Regardless of when he becomes eligible for arbitration, the 24-year-old will be under team control through 2015, which should give the two sides plenty of time to talk.