If so I recommend the following:
Let's say DL continues to be inept at signing free agents
Rather than overspend on aging or journeymen players, I suggest we save our money for one year, we continue to pay Clouiter his final year (rather than buy him out) and renogiate Pressing's contract. Frontloading it to give the team better cap options.
According to my numbers Pressing has $8.25 and 3 years remaining. We offer him a new contract at:
$6.33M 08-09
$1.25M 09-10
$0.75M 10-11
Now, this is way more than he is worth in 08/09 and he will quickly realize we are setting up an option to buy out his contract. But, even if we buy him out next offseason. That's still $6.33M + $1.33M (two thirds of $2M) so it's actually a good deal for him. He only loses $0.5M but can go play for another team.
It's almost the same cap hit ($2.77M) for us 08-09. Next offseason we can continue to play him 09-10 (same $2.77 cap hit) or buy him out. If we buy him out, the buy out cap hit is only $0.33M each year for 4 years. That's a cap savings of over $2M in 09-10 and again in 10-11. Combined with Cloutier being gone, that's over $5M in additional cap space next offseason (and the following).
Next offseason with Cammi a UFA, JJ Kopitar RFA's, the $5M is better spent on them. Plus we may have better interest in players from other teams wanting to play for us in 09-10 rather than this year.