Cleveland is in a unique position with its roster this summer. The team is currently built around Sexton, Darius Garland and Jarrett Allen.
Allen is will be a restricted free agent this summer. Sexton is extension-eligible this offseason, and Woo noted that he is "likely to seek a maximum contract."
Terry Pluto of Cleveland.com reported in May that the Cavaliers are preparing to "give Allen $100 million or more in a contract extension."
It doesn't seem like a smart use of resources for a Cavs team coming off a 22-50 record in 2020-21 and three straight losing seasons to have three players—potentially Allen, Sexton and Kevin Love—making at least $25 million.
Darius Garland's emergence last season would make it easier to justify moving on from Garland. He had a higher three-point percentage (39.5 to 37.1) and averaged more assists per game (6.1 to 4.4) than Sexton last season.
It also helps that the Cavs could be able to pick from at least one of Jalen Suggs, Jalen Green and Cade Cunningham in the draft, assuming they don't look to trade down.
Sexton's value is likely at its highest point so far in his career. The 22-year-old set career highs in scoring average (24.3 points per game), field-goal percentage (47.5) and assists (4.4) in 60 starts during the 2020-21 season.