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I am so paranoid about getting stuck in 'worst contract ever' status that player loyalty has basically gone out the window once I deem their demands to be unrealistic. In most cases, I just refuse to pay for the declining years of the early-to-mid 30s... and end up trading away fan favorites for prospects.
While I have little doubt that this approach serves me well in the long run... I still sometimes try to force myself to role play a real GM... "A real GM would never trade this guy... been here 10 years... multiple All-Star appearances... extremely popular... just give him the contract and pray for the best" ... But I almost never do that... occasionally if a guy has "iron man" durability and high work ethic I'll roll the dice on his 2nd FA contract into the 35-37 age range... but very rarely.
As far as this pitcher... that extreme backload is what stands out the most to me.. I could almost see that $46m making sense if some other huge veteran contract was dropping off the books the year before, but I doubt the OOTP algorithms are that in depth.
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