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Let's start with the obvious: Josh Freeman has not requested a trade, the idea that he will is mostly speculation based on one report, and we are all getting ahead of ourselves, here. Let's not treat this as a done deal. The truth is that Josh Freeman is most likely to stick in Tampa for the duration of his contract. If only because finding a trade partner will be difficult.
If a team wants to trade for Josh Freeman, they really have to believe three things: that Freeman will help them win immediately, that they can afford both his salary and the draft picks to trade for him, and that they want to give him a long-term contract extension.
Immediate Help
Can Josh Freeman help a team immediately? The most likely answer is 'no'. Not only would he have to be better than the team's incumbent starter, he'd have to pick up the offense in a couple of days before he can start. That's a lot to ask, and not very likely to happen. It's why you just don't see in-season quarterback trades, unless it involves the Oakland Raiders.
So, which teams could trade for Freeman as immediate improvement? I can't think of many teams. The Jacksonville Jaguars are an obvious team, with Blaine Gabbert and Chad Henne starting there, while the Minnesota Vikings are in trouble with Christian Ponder.
Beyond those two teams, though? The Jets might see immediate improvement over Geno Smith with Josh Freeman, but that's far from a given. Terrelle Pryor has been remarkably solid for the Oakland Raiders so far. The Cleveland Browns might get something out of Freeman they can't get out of Weeden.
But almost none of those options are slam dunks. Even when Freeman is the more talented quarterback, he doesn't know the offense. Immediate improvement is unlikely to occur by trading for Freeman for any NFL team.
High Price
If a team were to trade for Freeman, they would have to give up some draft picks to the Tampa Bay Buccaneers, although we don't know the price they would be asking for. But any team is going to give up some of its future to trade for a quarterback who may not be the answer for them.
Moreover, they have have the salary cap space to absorb Freeman's $8.5 million salary. Assuming he's traded with around 10 games remaining, they have to have at least $5 million in salary cap space. Of the teams mentioned above, the Cleveland Browns and Jacksonville Jaguars are the only teams with that kind of cap space.
Even if a team thinks they'll get immediate improvement, they need to be able to afford him, and willing to pay the required price. With the Jaguars being really bad this season, would they give up anything for this season? The Browns might, given that their defense appears to be fairly dominant.
Long-term contract
Needless to say, no team is going to give up anything for Freeman if they don't want to give him a long-term contract after the season. So which teams would want to tie their future to Josh Freeman at this point? If they believe they can fix his problems, he could be very good for a team that's willing to invest in him -- but that's quite a large risk to take.
So, which teams might be willing to take that combination of risks? Which team would be desperate enough to give up significant money and draft picks for a quarterback they could sign next year? It seems to me that the Jaguars, Browns and Vikings are the most likely candidates. But the Jaguars may just want to wait for next year's draft, while the Vikings will struggle to pay his salary cap figure. That just leaves the Cleveland Browns -- and they may just want to stick with Brandon Weeden, who has some potential himself.
If the Buccaneers do want to trade Josh Freeman at any point this year, finding any trade partner is going to be difficult.