Damian Lillard $31,626,953
C.J. McCollum $29,354,152
Jusuf Nurkic $12,888,889 (may have a "likely" bonus of 1.25M)
Zach Collins $5,406,255
Andrew Nicholson (stretched) $2,844,430
Anderson Varejao (stretched) $1,913,345
Anfernee Simons $2,252,040
Skal Labissiere $3,484,882 (qualifying offer - cap hold will be 7M)
Gary Trent Jr. $1,663,861
$91,434,807
http://www.basketballinsiders.com/portland-trail-blazers-team-salary/
That's for only 7 players so add 5 roster charges putting them in the 96-97M range depending on Nurkic's bonus. Skal might not be a part of the picture any more. So, somewhere in the 20-22M range for cap-space
but then you have to start backing out salary, or at least consider it will be a big factor
Say they sign Hood for the 5.5M tax MLE this summer. His cap-hold would be 10M in 2020. Now you only have 10-12M in cap-space
say they use both the 2019 and 2020 firsts to add "cheap" players. That will be at least 5M more in guaranteed salary. Now you're down to 5-7M in cap-space; maybe as much 9M if Skal is gone. But you've added 3 players which knock off 3 roster charges so you're back to near 10-12M in space
but if by some miracle Olshey can convince both Kanter and Hood to re-sign for the tax-MLE and non-Bird, then you'd have a 10M cap-hold for Kanter and a 7.8M cap-hold for Hood and your space is just about kaput
and of course, none of that accounts for Aminu or Layman. What happens with them? And there's still the possibility, however remote, of Curry signing for his non-Bird. He'd have a 6.4M cap-hold in 2020
in other words, yes, Portland could have some cap-space in 2020, but it sure looks like they'd need to take a step back next season to get there. Yeah yeah, I know...trade Turner yadayada