DeSean Jackson and Evan Mathis are different players with different circumstances, but it's hard not to look at the potential trading of both and wonder what Kelly and general manager Howie Roseman are thinking.
Despite being given several opportunities to say the Eagles weren't actively shopping Jackson or fielding calls from interested teams, Kelly didn't slam the door on mounting reports and evidence that the team is in fact doing so.
Asked Wednesday at the NFL owners meetings if he wanted the Pro Bowl wide receiver on his team, Kelly said, "I like DeSean. DeSean did a really nice job for us. But we're always going to do what's best for the organization."
Mathis hasn't come out and said that he thinks he's deserving of a new contract, as Jackson did two days after the season ended, but sources have said that he wants a raise. The Eagles, in turn, suggested a trade, but there haven't yet been any takers for the 32-year-old guard.
The 2014 base salaries for Jackson ($10.25 million) and Mathis ($5.15 million) at least match their production from last season and are comparable to what others are making at their respective positions. The feeling here is that the Eagles are more than willing to pay Mathis his salary but aren't as keen on meeting Jackson's current number.
And they most certainly aren't going to match either's demand for a new contract. The Eagles may have salary cap space, but they also have future extensions to hand out to young players and must remain fiscally sound if they want to have flexibility.
Roseman heads the business side of football operations, but Kelly did say that he has a "general overall concept of how" the Eagles want to allocate funds. He just isn't crunching the numbers.
"I don't deal with numbers. That's not my job," Kelly said. "My decisions are all: 'Where do guys fit scheme-wise?' . . . I don't look at it and say: 'I want that guy to make this much money, this guy should make this much money, that guy should make that much money.' That doesn't kind of fall into my domain."
But Kelly has his fingerprints all over how contracts are handed out. The Eagles wouldn't have 64 percent of their salary cap allocated to the offensive side of the ball - the most in the NFL - if it weren't for the offensive-minded Kelly.
But when it comes to the system vs. the player argument, Kelly seems to favor his scheme over the individual. Running back LeSean McCoy and Jackson, for instance, had their most productive careers in his offense.
"I don't think our offense has ever been predicated on one player," Kelly said. "I think we used three quarterbacks last year. We used multiple running backs. Our tight ends are integral to what we do. I think we have an outstanding offensive line. It's never been just about one guy."
Trading Jackson and/or Mathis may seem like a product of hubris, but difficult decisions have to be made in the salary cap age and sometimes star players must go.
And an innovative system allows for successful teams to get by with middling players at certain positions and without overspending, although losing Jackson add/or Mathis would certainly not improve the Eagles.
Kelly has adopted the good cop role many NFL coaches take on opposite the general manager bad cop. He said he understood Mathis' desire for a new contract and said he hopes all of his players "get paid a billion dollars."
But he knows that isn't possible and neither is his avoiding the business side of building a team.
In the previous Eagles regime, Andy Reid played good cop to Joe Banner's bad cop. But Reid had final say on football matters and ultimately gave the thumbs up or down on a player. Kelly has that power now, and whether the players realize it or not, he's the one pulling the strings.