As it stands right now, Cassel will be an UFA after this season and 2010 will be uncapped which means that if he agrees to your deal he will be an RFA after the 2009 season. In 2010 it will take 6 accrued seasons, not 4, to be an UFA.
I just can not see Cassel agreeing to a deal that may make him an RFA in 2010 when he is weeks away from being an UFA in 2009.
I agree it would take more than a one year deal to pique his interest in not rolling the dice for a potential bonefide starters contract in 2009. But the fact that he is potentially 4 months worth of a few weeks away yet from being a UFA in 2009 could be a mitigating factor in a decision. Of course that works both ways. Not sure Cleveland is thrilled they were able to talk Anderson into a 3 year deal right about now...
There are going to be bumps (and potential bruises) along the road to that next contract. Anderson hasn't looked nearly as good since the last weeks of the 2007 season when the league seemed to be catching up with him. Which is why after waiting that long I said then they should have gone the RFA route and either had him cheap or sold high. We don't have that option with Cassel unless we manage to create it. Which is why I would at least take a shot at due diligence by trying to see if it could be achieved while they have the long season risk factor to use as leverage.
If they don't I'm fine with either a tag and trade if he plays really well into the playoffs or thanking him for outperforming his draft position for 4 years and providing tremendous value already in that respect. Because while **** can happen I'm fairly confident based on what we know thus far that Tommy will be ready to go week 1 of 2009.
I think it's not out of the question that he might take a deal that guarantees him several million between now and 2009 if it implicitly guarantees him (say via a prohibitive 2010 roster bonus in 2010 that he wouldn't sneeze at either...) entering the FA market in the potentially uncapped bonanza season.
Say for argument sake he gets $5M in signing bonus next month for a 3 year extension (tacked on to being signed through 2008) through 2011 with another $1.5M in guaranteed salary for 2009 and a roster bonus of $1M due on September 1. That's almost $8M over 2 seasons with projected cap hits of $1.7M in 2008 (up $1.25M over his current cap hit for this season) and $2.25-3.25M for 2009 position insurance. (Dead cap if traded before 2009 season $3.75M spread over 2 seasons as we draft with the picks you bring in...). Add a roster bonus of $5M and a guaranteed salary of $2M for 2010 and more of the same for 2011 (none of which he will ever see here unless something thoroughly unthinkable happened in which case you're getting more than chump change), toss in a few performance/playing time escalators for good measure and you got a 3 year $20M deal that could be worth $25M with escalators but is really likely a 2 year $7.5M and your on to your life as a highly sought after QB via trade to some team who will extend you with a double digit signing bonus of thier own in 2010.
PS Matt Schaub managed to get to his next big deal as a starter without undue exposure. Everyone laughed at Atlanta for screwing up that one given what happened to Vick just weeks later. Only problem is once he started starting regularly, Matt got hurt. Luckily for him he had signed a new starters deal with Houston before that transpired. But how many starts did it take before he was injured? Not nearly as many as this Matt is penciled in for over the next 18 weeks or so god willing without the insurance of a contract for 2009 and beyond... just saying.
