It's a question that certainly raises a lot of argument and debate, but one that is worthy of discussion as we go into the 2013 season.
The Arizona Diamondbacks just recently went through a very similar situation when they traded two-time All-Star and multi-tool threat Justin Upton to the Atlanta Braves for a nice package of prospects and Martin Prado.
Sure, it must have been tough on the fans to lose a player like Upton, but did the return on his value—at least on paper—outweigh the loss?
Though it's never easy to lose a 25-year-old stud like Upton, the D-Backs certainly got a nice return in compensation for his loss, saved some money and potentially acquired key pieces to their lineup for many years to come.
The question is: Will the Padres third baseman pull the same weight in return if he were sent shipping to another team?
Headley, who is in for a substantial pay-raise from the $3.475 million he made last year, will not be hitting the free-agent market until 2015. He's 28 years old, just came off of the best season of his career—winning a Silver Slugger and a Gold Glove award—and is a shining example of how a leader should act on and off the field.
Last season, when it seemed almost inevitable that he would be traded before the deadline, Headley proved his value to the baseball community and had Padres fans nervously anticipating the very familiar news of yet another star player being traded away for a package of players.
Fortunately, this day never came to fruition, and Headley took home National League Player of the Month awards in both August and September while further raising his value in the trade market.
Now going into 2013, the team will face this same dilemma if Headley has another breakout year and the Padres find themselves in the middle of the season at the bottom of the National League West.
If the Padres aren't going to extend Headley, it's absolutely imperative that they get a package of players similar to the Upton deal.
Upton brought over one of the Braves' highest-valued pitching prospects in Randall Delgado, highly touted shortstop prospect Nick Ahmed and pitcher Zeke Spruill, minor league first baseman Brandon Drury and, as previously mentioned, Martin Prado.
Quite the package for Upton and third baseman Chris Johnson.
Headley, who will still most likely make under $10 million next season, at his current value should bring back close to the same than what the Upton trade gave the D-Backs. And if he doesn't, then trading him should be out of the question.
If the day does come that the front office sends Headley packing, they need to—at the very least—acquire two top-of-the-line pitching prospects, seek depth in the infield and possibly try to add a right-fielding prospect.
Will this scenario ever happen?
I hope the Padres plan to extend Headley and build around him for the future, but if they don't, they had better get a solid package of players anchored with some very deep pitching prospects.
If not, general manager Josh Byrnes should get ready for an onslaught of backlash, criticism and many more empty seats at Petco Park.