One reason why it may be so difficult to hammer out an agreement is that one of the primary weapons at the team's disposal, the franchise tag, comes with it a prohibitive price tag.
Bailey would be due a 20 percent bump on his 2010 salary, meaning that securing his services next season alone would bring with it a cap hit of about $15 million. That's more than 10 percent of the total roster outlay.
Bailey, who recently played in his 10th Pro Bowl, a record for cornerbacks, isn't adverse to that franchise designation, saying "that's not a pay cut." But the fact remains the best solution for both sides would be a long-term deal, something that Denver in its current rebuilding phase may not be willing to dole out.
The team recognizes Bailey's contributions as both a player and leader but, given the team's current state, seems to be balking at allotting big money to a player who turns 33 years old next season, despite his current high level of play. The NFL's uncertain labor situation factors in, too, from a financial perspective.
The fact remains that with the scheduled March 4 start of the new league calendar, the exclusivity period to negotiate with Bailey also ends, and, given the player's desire to win a Super Bowl, that open door at this point seems to be akin to a path out of town.
Bailey does like Denver and the city and has said publicly many times he would like to make things work with the Broncos.
He's also a realist who, while in Honolulu, heard sales pitches from prominent players like Baltimore's Ray Lewis about how the grass may be greener elsewhere - and it is.
"I think we're going in a good direction," Bailey said of the Broncos while completing his Hawaiian excursion. "I don't think can get worse. One thing I do know is Coach Fox is a good defensive-minded coach and won a lot of games throughout his career as both an assistant and head coach. I know he can do a good job for the Broncos. It's all about who they bring in to try and fill the roster."
Denver's offseason moves in that regard figure to be one-sided toward the defense. The team is coming off a season in which it allowed 471 points, two shy of the franchise record, while yielding 6,253 yards - a whopping 5.9 per play.
Letting Bailey leave isn't addition by subtraction. He is inarguably the team's best defensive player even at this late stage of his career. But the fear is his skills will begin to diminish as he ages to justify another big contract. That contention is dulled somewhat by the fact Bailey is willing in the future to move to safety should that occur.
A willing tackler and a player with an uncanny ability to see the action unfold, that transition - should it eventually be needed - isn't a stretch. Think Rod Woodson late in his career.
Dallas, Miami and Tampa Bay are just some of the team that may need help at cornerback in free agency.
"I'm trying not to think about it too much because there are so many options," Bailey said. "They can over me a new deal, franchise tag me. It's a waiting game. I've been through this before so I'm not going to lose any sleep over it."
The new three-man hierarchy running Denver's personnel department has been referring to itself as a 'three-legged stool,' meant to reinforce the type of solid foundation the organization will have moving forward.
Executive vice president of player personnel John Elway, general manager Brian Xanders and new head coach John Fox comprise the 'legs' of that stool and the buzzword is that consensus will be the guiding force in the decision making process moving forward.
It's also a not-so-veiled response to the 'pogo stick' parameters that the team employed when Josh McDaniels was coach and a huge player in the comings and goings on the roster the last two years.
One reason McDaniels is gone, the company line goes, is that he had too much autonomy to the detriment of the organization in a position of power for which he wasn't prepared.
That may be partially true, but two factors must be considered. First, at McDaniels' introductory press conference prior to the 2009 season, team owner Pat Bowlen and Co. went to great lengths to say the new model wouldn't be include a central power figure. But the organization's largesse resulted in McDaniels sliding right back into the Mike Shanahan one-man show model that for many years hadn't served the organization well.
Digging deeper, Xanders particularly is going to have to prove his worth as a personnel evaluator and deal maker. It's too convenient to say that McDaniels had final say and Xanders constantly stepped aside in deference to the hierarchical structure and McDaniels' place above him on it.
No one will truly know how much sway Xanders had in some of the trades and breakdowns with the likes of Jay Cutler, Brandon Marshall and Tony Scheffler. And maybe in those latter three cases he was an innocent bystander while McDaniels' ego ran amok.
The point is there are skeptics surrounding Xanders and he now has a clean slate to help rebuild a flawed roster with his name and reputation firmly affixed. He should be given that opportunity with the usual critical - but not prejudiced - eye.
Elway will be under a similar microscope. The way the decision-making process in the front office is being cast this time around following Fox's hiring is that Elway has final say if there's a dispute.
A brilliant NFL player, Elway's acumen in such a critical personnel role is limited to his time with the Arena League's Colorado Crush. His close bond with his late father, Jack, a longtime scout, did teach him about what to seek in players as much as the former quarterback's own countless hours playing and game-planning for 16 seasons.
But this is his first high-profile NFL position with that type of sway, and given the learning curve he'll experience to go along with Xanders' first full-time power grab, Fox will play a key role in whether the three-legged stool retains its balance.
Fox knows what he wants from a personnel standpoint to especially rebuild Denver's defense, and he has to quickly morph his vision with the scouting parameters of Denver's staff in order to put together an accurate draft board that currently shows the Broncos with three of the top 50 picks.
Building that symmetry and like thought is a key reason Denver is sending its entire new coaching staff, front office hierarchy and scouting department to the Senior Bowl. It's not only a way to find premier talent but a way for the team to get on the same page in terms of its philosophy and methodologies.
Or as the other Dove Valley buzzwords go, begin building consensus.
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