Attempting to sign any player to an extension during the offseason or during the regular season can be awfully tricky.
Factor in a history of major injuries to go along with an incredible amount of talent and you've got an even more puzzling dilemma.
Such is the case when it comes to Josh Johnson and the Toronto Blue Jays.
Johnson's current deal is set to expire following the 2013 MLB season and after the success he has had in the past, he will surely be looking to cash in on his past successes, regardless of injuries.
And after seeing some of the recent deals that have been inked by major league clubs and star players, some teams will undoubtedly pay big money to Johnson and hope he can stay healthy and pitch to his potential.
This puts Blue Jays GM Alex Anthopoulos in a tough spot.
Johnson was one of his marquee acquisitions this offseason, and finding a way to retain his services would do wonders for the Jays' future prospects.
Johnson did, however, struggle in 2012, posting a 3.81 ERA, the worst of his career (not including the 2007 season when he only started four games).
This is because 2012 was Johnson's first year back after undergoing major surgery on his throwing arm, which sidelined him for almost the entirety of the 2011 season.
Yet Johnson is also one of the most talented pitchers in all of baseball.
With one of the premier sliders of any starter in MLB and a fastball that can reach 97 miles per hour, Johnson is nearly unhittable when healthy.
Take his 2009, 2010 and 2011 seasons for example.
In 2009, Johnson made his first career All-Star Game appearance, and finished the season with a respectable 3.23 ERA, 209 innings pitched, 191 strikeouts and a 15-5 record.
Should Toronto re-sign Johnson now or wait?
In 2010, Johnson made his second consecutive All-Star Game and finished the season with a National League-leading 2.30 ERA (he was three one-hundredths of a point behind Felix Hernandez for the best ERA in all of baseball), more than a strikeout per inning pitched, an 11-6 record and finished the year fifth in National League Cy Young balloting.
In his abbreviated 2011 season, Johnson was well on his way to his third straight All-Star Game appearance, posting a WHIP below 1.00, an astonishing ERA of 1.64 and a record of 3-1 through nine starts before suffering his injury.
So clearly, the talent is there.
In fact, when healthy, a case can be made that Johnson is one of the best pitchers in all of baseball. The only knock on him thus far has been that he struggles to pitch a good amount of innings each season.
Yet the potential for injury isn't the only risk regarding Josh Johnson. After his 2012 season, one has to question whether he will be able to fully recover and once again reach 97 mph with his fastball or if he'll ever be able to throw his slider as he once could.
If Anthopoulos were to re-sign him in the next few months at a reduced rate and Johnson were to rediscover his dominance, it could really pay off.
If Anthopoulos decides to wait and see what happens this season, it could be to Toronto's detriment if Johnson pitches really well and becomes too expensive for Toronto to re-sign.
On the flip side, if the Jays do give him an extension and he never becomes the top-of-the-rotation starter that the team needs, it could prove to be a contract that really hinders Toronto going forward.
No matter what Anthopoulos does going forward, some will question his decision.
Finding ways to keep your roster intact is always tough for a general manager. For Toronto and Josh Johnson, however, it's an even more difficult conundrum.