First things first - I like Andrew Ladd. He plays a solid game at both ends of the ice, contributes more than his share offensively, is physical and serves as team captain. There really isn't a glaring weakness in his game (late game penalties notwithstanding).
It is, however, time to trade him.
Before you light the torches and sharpen the pitchforks, bear with me. Ladd is in the last year of his contract, and given the current state of talks - read: seemingly going nowhere fast - the Winnipeg Jets would be better served by moving a still valuable asset and re-focusing their efforts on getting Dustin Byfuglien inked to a new deal.
It comes down to a perfect storm of three major factors: his age, his style of play and his expected contract.
At 30 years old, Ladd is no longer a spring chicken. Your body doesn't recover the way it did when it was 25, and his peak years are (statistically speaking) behind him. It doesn't help that he's subjecting that body to a very physical play style, and it won't be getting any easier for him to avoid or recover from injuries, particularly as he gets older. Ladd already spent half of last year battling a sports hernia (requiring surgery over the summer) and has missed time during this season's training camp.
The deal Ryan Kesler signed with Anaheim this summer (6 years, $6.875M AAV) sets an approximate high-water mark for the Ladd contract. It is both too long, and too much money. It is especially a problem for someone who plays like Ladd, a player who as time rolls on will likely see a decline in ability, an increase in time spent injured, and an ever-decreasing role. You could look at the situation LA was in, with Mike Richards and his anchor of a contract vs. diminishing returns on a rapidly fading skill set, as an example of what may be in store for Ladd.
Now, this is not to say Ladd won't defy expectations. Power to him if he can. More often than not though, power forwards start to fade post-30. If he's lucky and good, he might be able to extend out past 33. But I have difficulty seeing Andrew Ladd in a top-6 role at 35, and I'd have a real problem with the Jets management paying a 35-year-old depth player well over six million dollars a year.
So if Kevin Cheveldayoff is smart, he moves Andrew Ladd now before the season really gets underway, to maximize the return he can get. As is, if there's no deal in place by the trade deadline, it'll be safe to say that Andrew Ladd will be leaving Winnipeg, with exactly zero assets coming back.