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If he plays at his historical level, quite likely true. Here is the nightmare scenario for some. Bears go 6-10 and draft the heir apparent, but retain Cutler after a 30 TD 12 INT 89 passer rating year, for his last guaranteed money year. He starts the season and leads the Bears to a 10-6 record with a wild card victory and loss in the divisional round. He ends the season 32TD 10INT 93 passer rating. He is now a 34 year old QB with a very reasonable contract (Cap rank #16 QB in 2017) playing at an above average level, but near untradable due to age.
What do you do then? Cut him and go with the unknown or ride him out?
I don't see how that's a problem at all. If they ride with Cutler because he's playing well, but still have a "backup of the future," there is an option to go to if Jay starts to falter.