4. Dennis Schroder
Schroder turned down a massive deal from the Lakers in hopes of landing more in free agency in 2021, but it did not work. The 6’1 guard failed to sign before cap space dried up and ended up taking a one-year $5.9 million contract with the Celtics. He had helped his team to the playoffs in seven of the last eight years and offered some speed and scoring punch at the point.
His tenure in Boston lasted just 49 games. Ime Udoka wanted defense, which forced Schroder back and forth between starting and coming off the bench. His one-year contract made it nearly impossible for the Celtics to re-sign him for the following season. His fit next to Marcus Smart was problematic and Schroder leaned a bit too hard into a score-first mentality.
The Celtics traded Schroder, Enes Freedom, and Bruno Fernando to the rebuilding Rockets at the deadline for Daniel Theis. It paid off as the Celtics won the Eastern Conference before losing to the Golden State Warriors in the NBA Finals.
Dennis Schroder just did not fit in Beantown, and the team improved after he was traded to Houston. The 6’1 point guard ended up back on the Lakers the following season before joining the Raptors in the summer of 2023. He never recouped the millions he turned down, but Schroder remains a skilled point guard and playmaker.