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At the (awesome) site Fangraphs, their "never give a player a nickel you do not have to" mantra gets a little off-putting, but --- > Iwakuma just flat deserves to make more money next year.  If you ask me.
Re-write this one, give him $15M or something next year, $17-18 the next two, with a $2-4M buyout and another $15M in year four.  Slide some money to signing bonus if he wants (ha!) and you've got a match for Zach Grienke, at 30% of the dollars.   And you can be proud of Iwakuma, because he's your org player.
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Price point?
If I'm in his shoes, I'm thinking "$50M in salary from here ... added to my earnings so far ... and I'm set.  I'll be able to get any three houses in the world I (reasonably) want, whatever car collection, all the travel I care for ... I'll have everything I could possibly enjoy.  Let's lock it in."
But who knows.  Maybe $100M is necessary before you can really start wasting money the way the Manny Way?  :- /
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Remember when Sports Weekly asked me to write a column predicting Ichiro's fate?  I wrote a sharp column predicting that he'd be gone, and not one month later the M's announced a big extension.  Shows you how far to trust me on M's extensions :- )