Following kingdave902's proposed trade, I have slightly modified it and included a hypothetical trade of De'Andre Hunter.
TRADE #1 Details
CLE: Jrue Holiday, Tari Eason
HOU: Darius Garland, Blake Wesley
POR: Fred VanVleet, Dorian Finney-Smith, 2027 HOU 1st (via PHX), 2028 HOU 1st (swap)
TRADE #2 Details
CLE: Ayo Dosunmu, Jalen Smith
CHI: De'Andre Hunter, 2031 CLE 1st (top 5 protected)
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STARTING FIVE
HOU:
PG: Darius Garland
SG: Amen Thompson
SF: Kevin Durant
PF: Jabari Smith Jr.
C: Alperen ΕengΓΌn
POR:
PG: Shaedon Sharpe
SG: Deni Avdija
SF: Sidy Cissoko
PF: Toumani Camara
C: Donovan Clingan
For next season, Fred VanVleet or Damian Lillard would be the starters in the starting lineup, at the expense of Cissoko
CHI:
PG: Josh Giddey
SG: Coby White
SF: De'Andre Hunter
PF: Matas Buzelis
C: Nikola VuΔeviΔ
CLE:
PG: Jrue Holiday
SG: Donovan Mitchell
SF: Jaylon Tyson
PF: Evan Mobley
C: Jarrett Allen
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BACKUP FIVE (CAVS):
PG: Craig Porter Jr.
SG: Ayo Dosunmu
SF: Tari Eason
PF: NaeβQwan Tomlin
C: Jalen Smith
REST OF BENCH (CAVS):
PG: Tyrese Proctor, Lonzo Ball
SG: Sam Merill
SF: Max Strus, Tristan Enaruna
PF: Dean Wade, Luke Travers
C: Thomas Bryant, Larry Nance Jr.
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LINEUP IN THE FINAL MINUTES (CAVS):
PG: Jrue Holiday
SG: Donovan Mitchell
SF: Jaylon Tyson
PF: Jalen Smith
C: Evan Mobley
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Candidates for waiver: Larry Nance Jr., Lonzo Ball