Okay, I have a pretty decent player who is 30 years old. I am in the "resign free agents" period of the pre season. The guy is asking for a 3 year $15 million deal, at $5,000,000 per year. I want to keep the guy around for 4 years and then should have a replacement ready for him.

He says that unless I surprise him he will opt for free agency. So, therefore I need to offer him more than his demands.

My question is if I offer him the following deal, will he consider it a better offer than his demands:

year 1 = $4mm, year 2= $4mm, year 3 = $3mm, year 4 = $2mm, year 5 = $4mm with a mutual option.

My doing it this way I am offering him $17mm, but only $13mm is guaranteed. Will he look at it as a 5 year $17mm deal, or a 4 year $13mm deal?

In my experience, if you want to offer a longer term than the player is asking for, you'll have to offer the same yearly rate (or more) or he'll decline.

Also, the "unless you surprise me" line typically means you can add another year at that rate, and he'll find it adequately surprising to decide to re-sign with you.

Short answer: No. He won't take your offer.

Thanks.