There comes a time when a team can only realize its championship potential by taking a chance that the average fan would deem irresponsible. It's the harsh reality facing the Cleveland Cavaliers as they stare down the possibility that their once promising vision may be hitting the proverbial wall.
If the Cavaliers are willing to take a chance, then there's a bold trade idea they should consider: Swapping Darius Garland for Jrue Holiday.
Garland is a 25-year-old playmaker who's already a two-time All-Star with three different trips to the playoffs on his résumé. He's proven capable of running a top-tier offense, led the Cavaliers to a 22-win improvement the year before Donovan Mitchell arrived, and offers value both on and away from the ball.
With this in mind, it's hard to sell the merits of trading Garland for Holiday, who's 35 years of age and will still have two years and $72 million remaining on his contract after 2025-26.
The value of fit can't be overstated, however, and Holiday is exactly what the Cavaliers need. He's a top-tier defensive tone-setter whose leadership and locker room value has been praised at every stop. Moreover, he's a two-time NBA champion who knows what it takes to win.
A Garland for Holiday trade may not be a fair talent-for-talent move, but a point guard swap can be the foundation of a fruitful trade that truly opens the Cavaliers' window.
Darius Garland for Jrue Holiday would give Cavaliers everything they lack
It must be said: Garland has been turned into a scapegoat for the Cavaliers' shortcomings. In no way is this trade intended to be commentary on his quality as a player, nor is it a condemnation of him as some kind of anchor who's keeping Cleveland from moving forward.
The importance of fit simply can't be overstated, however, and Holiday's strengths are exactly what the Cavaliers need at the point guard position.
Garland and Donovan Mitchell have formed an undersized backcourt that inevitably lacks an ideal level of defensive consistency. Holiday, meanwhile, is a 6'4" and 220-pound guard who can defend multiple positions and has six All-Defense nods on his résumé.
Holiday has also proven to be invaluable in his ability to excel both with and without the ball, with championships delivered in such a capacity in both Boston and Milwaukee.
With Holiday's defensive acumen and offensive versatility, the Cavaliers could finally explore the true potential of a team led by Mitchell. He could take on difficult defensive assignments, and more importantly, set the tone for his teammates with his intensity and communication.
With 2025-26 season averages of 16.7 points, 8.3 assists, 5.3 rebounds, 1.6 steals, and 2.6 three-point field goals made per game, it's clear Holiday can still produce meaningful numbers, as well.
Sometimes, fit is more important than talent
The true value of this trade, however, is what won't be seen on the stat sheet. The Cavaliers have lost five-game series during the second round of the playoffs in consecutive seasons, and are now on pace to have to go through the Play-In Tournament to simply reach the postseason.
By the look of things, it doesn't seem as though Cleveland is trending toward the Conference Finals appearance they've failed to make during the Mitchell era.
If anything can change the Cavaliers' course, it's likely to be the addition of a player who knows the ins and outs of winning in the NBA. Holiday is exactly that, with perspective and leadership qualities that are not only proven, but heralded in every corner of the Association.
Cleveland would clearly ask for more than just Holiday based on age, injury history, and contract status, but an All-Star swap with Portland could prevent their window from slamming shut.