Going out in the first round against the New York Knicks was not what the Cleveland Cavaliers envisioned in their first season with Donovan Mitchell on the roster, and second-guessers around the NBA were wondering why the Cavs even bothered to break up the speed-and-size roster from the 2021-22 season that nobody could match up with.

They had Collin Sexton and Darius Garland in the backcourt, plus three 7-footers in the frontcourt with Lauri Markkanen, Jarrett Allen, and Evan Mobley.

But they did what they did because Utah was making an All-Star available, and only time will tell whether the 2023 offseason made them better. The Cavs have added Max Strus in a sign-and-trade with Miami and signed free agents Georges Niang and Ty Jerome. Yes, those are role players.

But having the proper role players surrounding your superstar is what winning in the NBA is all about, and true believers in the Cavs can get them this summer at +3000 to win the NBA title. If they are one player away, and that player comes before the 2024 trade deadline, perhaps we shall have a new member of this Top 10 list next summer.

Cleveland Cavaliers Trade History

When discussing the Cleveland Cavaliers’ trade history, you have to be aware of the Ted Stepien rule. It is a rule that prohibits an NBA team from trading away too many first-round picks (teams must have one every other year) and was adopted after Stepien traded away five consecutive first-round picks, covering 1982 until 1985. Stepien is widely considered one of the worst owners in the history of U.S. professional sports.

Ranking the Top 10 trades in Cleveland Cavaliers History

  1. Lauri Markkanen, Collin Sexton, Ochai Agbaji, and five first-round picks (two are swaps) for Donovan Mitchell (Sept. 3, 2022)

This one is only checking in at No. 10 because until Mitchell wins a playoff series, he has not been successful. Hey, those are our standards, and five first-round picks along with two darn good players in Markkanen and Sexton was a whole lot of lumber.

  1. Kevin Johnson, Tyrone Corbin, and Mark West to the Suns for Larry Nance (Feb. 28, 1988)

Nance was part of one of the best starting fives in the NBA during the late 1980s along with fellow All-Stars Mark Price, Ron Harper, and Brad Daugherty. His teams always played well until they hit a roadblock in Michael Jordan and the Chicago Bulls time and time again in the playoffs. 

  1. A future No. 1 pick to the Golden State Warriors for Tyrone Hill (July 15, 1993)

Hill became an All-Star in 1995 for his strong and steady play and set the Cavs’ field-goal shooting percentage record that season, ranking second in the league overall at .600. In the process, he solidified his status as one of the pillars of the team along with Terrell Brandon, another All-Star player for the Cavs. 

  1. Dion Waiters to the Thunder. Lou Amundson, Alex Kirk and a 2019 second-round draft pick to the New York Knicks for Iman Shumpert and J.R. Smith (Jan. 5, 2015)

Others might rank this higher, but Smith infamously forgot that Cleveland was out of timeouts and called one during the NBA Finals, resulting in a technical foul that doomed the Cavs to a loss. Nonetheless, he was a terrific shooter who went on to become a terrific competitive college golfer when he returned to college after his NBA career ended.

  1. Roy Hinson to the Philadelphia 76ers for a No. 1 pick (Brad Daugherty) (June 16, 1986)

Daugherty, a No. 1 overall pick, can still be found at or near the top of several all-time categories in franchise history, including points (third) and rebounds (fourth). His uniform No. 43 has been retired by the franchise.

  1. Ron Brewer to Golden State for World B. Free (Dec. 15, 1982)

Older generations of Cavs fans remember World B. Free as the man who brought excitement back to Richfield Coliseum in an era when then-owner Ted Stepien had emptied the seats due to his mismanagement of the team.  Free turned his career around with the Cavs. He played just over three seasons with Cleveland, averaging 23.0 points.

  1. Butch Beard to the Seattle SuperSonics for Lenny Wilkens (Aug. 23, 1972)

Wilkens came to the Cavs after 12 superstar years with the St. Louis Hawks and the Seattle Sonics. He immediately made an impact by leading a young Cleveland franchise to a nine-game improvement from the previous year.

  1. Terrell Brandon and Tyrone Hill to Seattle for Shawn Kemp (Sept. 25, 1997)

At a time when the Cavs were starved for star power, they brought in a player whose tenacity was his trademark in Seattle. He became the face of the franchise for three seasons and was a starter for the East in the All-Star Game in 1998. His scoring average topped at 20.5 points during the 1998-99 lockout-shortened season

  1. Anthony Bennett, Andrew Wiggins and a trade exception to the Timberwolves for Kevin Love (Aug. 7, 2014)

Bennett was one of the all-time No. 1 overall draft-pick busts, Wiggins was still just a prospect, and Love was a double-double machine. In Game 7 of 2016 NBA Finals, Love etched his name in Cavs lore, defending Golden State Warriors All-Star Stephen Curry in the closing seconds. The 6-foot-10 forward stood his ground against one of the best ball-handlers in league history to force a missed 3-point shot. Love's terrific defensive stand is now known as “The Stop.”

  1. Jamario Moon and Mo Williams to the Clippers for Baron Davis and a 2011 first-round draft pick (Kyrie Irving) (Feb. 24, 2011)

Irving came to the Cavs in uncertain times. LeBron James had announced that he would be “taking his talents to South Beach” a year before (2010). As a result, Kyrie became the face of the franchise. In his rookie season, he averaged 18.5 points, 5.4 assists, and shot 46.9 percent from the field, including a 39.9 percent mark from beyond the arc. Not until 2014 did Cleveland's Big 3 of James, Irving, and Love come to be. In the wake of James' decision to return to the Cavs, Irving signed a five-year, $90 million contract extension. This trio would go on to compete in the NBA Finals for the next three seasons.

Parameters of Rankings

When it comes to Cavs history, so much of it has been defined by the LeBron James eras. But this franchise was very competitive in the 1990s when they had the misfortune of going up against Michael Jordan and the Bulls, and the franchise had some ridiculously bad years under the ownership of Ted Stepien, the guy who they named the “Stepien Rule” after. That rule required a team to have a first-round pick in every other draft, at a minimum. Cavs history dates back to 1970 when they entered the league as an expansion franchise, and 53 years of history had to be considered here.

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