Kaep's contract is a bit weird. He's only guaranteed $13M and the rest of the $60M guarantee comes in the form of an injury-only guarantee, so if the team cuts him there's minimal impact and he won't get that cash. It also has a reverse bonus built into it. Essentially he has an annual de-escalator of $2M. If he doesn't reach certain hurdles (doesn’t take at least 80 percent of the snaps or if he fails to lead the team to the Super Bowl or to be named first-team or second-team AP All-Pro) the 49ers get back that cash.
Anyway, here's the actual cash flow into his pocket if the deal holds:
2014 $13,178,000
2015 $14,800,000
2016 $16,300,000
2017 $18,900,000
2018 $19,400,000
2019 $21,200,000
2020 $23,400,000
Not bad. Let's compare to Cutlers:
2013 $8,970,000
2014 $22,500,000
2015 $15,500,000
2016 $16,000,000
2017 $15,000,000
2018 $16,000,000
2019 $20,000,000
2020 $21,700,000
The deals are really close. I'd say there are a two gaps:
1 - Kaep is younger, so there's a larger chance he can live out the deal
2 - Kaep's guarantee of $60M is largely an injury only guarantee, so essentially you can look at it as a $13M guarantee, which is a lot less. This actually is reflected in the cap savings where the 49ers could cut him next year and take the dead cap space fee of $9,862,400, but create roughtly $7.4M in additional space. Conversely if the Bears wanted to do the same with Cutler they would have $19,500,000 in dead cap space and 0 cap space created.
Overall Kaep's deal is very close with less long term committments despite the falsely advertised '$60M guaranteed'.