The Cleveland Cavaliers are chasing their second NBA championship, and they’re doing it with a roster that blends youthful energy with a touch of championship pedigree. While stars like Donovan Mitchell and James Harden have yet to secure a ring, three players on the current Cavs have already tasted victory elsewhere. Each brings a unique story of how they earned their hardware, and their experience could be a crucial factor in Cleveland’s playoff push.

The most recent addition is Peyton Watson, whom the Cavaliers acquired earlier this week to address their long-standing need for a reliable wing. Watson had a breakout 2025-26 season, averaging 14.6 points, 4.9 rebounds, and 2.1 assists, cementing himself as a starter after years as a reserve. His journey to Cleveland began when the Oklahoma City Thunder selected him with the 30th pick of the 2022 NBA Draft. Shortly after, the Denver Nuggets traded for him, sending JaMychal Green and a protected 2027 first-round pick to the Thunder. Watson’s rookie season with Denver ended in glory: the Nuggets defeated the Miami Heat 4-1 in the 2023 NBA Finals, giving him a championship ring in his debut year. Now, he joins a Cavs team hungry for its own celebration.

Another player with Nuggets ties is backup center Thomas Bryant. Bryant started the 2022-23 season with the Los Angeles Lakers but was later dealt in a four-team trade that landed him in Denver. He played 18 games for the Nuggets that season, averaging 4.6 points and 3.3 rebounds, and earned a championship ring as part of the same title-winning squad. Bryant’s journey has been one of adaptability, moving from a starter in L.A. to a role player on a championship team, and now to Cleveland where he provides depth behind the Cavs’ frontcourt.

Sam Merrill’s ring came earlier, with the Milwaukee Bucks in 2021. Drafted by the New Orleans Pelicans in 2020, Merrill was traded to Milwaukee days later in a four-team deal. He appeared in 30 games for the Bucks during the regular season, and by the end of the playoffs, Milwaukee had overcome the Phoenix Suns in the NBA Finals. Merrill’s sharpshooting and experience as a role player on a title team make him a valuable asset for the Cavs as they look to space the floor and make clutch shots.

These three players—Watson, Bryant, and Merrill—are now gearing up for a significant season with Cleveland. The Cavaliers have built a roster that mixes veteran savvy with young talent, and the presence of players who know what it takes to win at the highest level could be the difference-maker. Donovan Mitchell and James Harden, both elite guards with impressive individual accolades, remain without a ring. But playing alongside seasoned champions may help them unlock that final piece.

Cleveland’s path to a title is not easy. The Eastern Conference is stacked with contenders, and the Cavs will need every ounce of experience from their championship alumni. If all goes well, Bryant, Merrill, and Watson could find themselves celebrating another championship—this time in Cleveland. The team’s front office clearly values the intangibles that come with winning, and these three players embody that mindset.