The early 2020s in the NBA have been defined by dynasties, upsets, and the rise of role players who embody the “3-and-D” archetype—reliable three-point shooters who defend at a high level. Among this new wave of tournament-definers, three names emerge with a shared distinction: Jrue Holiday, Kentavious Caldwell‑Pope, and Alex Caruso are the only players to win at least two NBA championships in this decade, and each has done so with two different franchises as.com+15reddit.com+15m.facebook.com+15. Their parallel paths reflect both personal excellence and a transformation in how modern teams are built.
Jrue Holiday secured his first ring in 2021 with the Milwaukee Bucks and followed it up in 2024 with the Boston Celtics. Kentavious Caldwell‑Pope won his in 2020 with the Los Angeles Lakers and again in 2023 with the Denver Nuggets. Alex Caruso claimed his first in the 2020 Lakers championship, then added another in 2025 with the Oklahoma City Thunder . These facts, simple on the surface, are part of a larger narrative: the ascent of players who may not fill highlight reels nightly but whose impact is felt most when the stakes are highest.
Mechanically, these three excel in what basketball analysts refer to as “3-and-D”—threats from deep who also anchor perimeter defense. Holiday’s veteran savvy, Caruso’s relentless hustle, and Caldwell‑Pope’s two-way consistency have not only earned personal accolades but also helped sustain championship-level systems.
Holiday began the decade as a new addition to Milwaukee via trade, swiftly becoming integral to the Bucks’ 2021 title run. He averaged team-high steals and recorded a memorable near triple-double in Game 5 of the 2021 Finals, catalyzing Milwaukee’s win en.wikipedia.org. His arrival helped break a half-century drought for the franchise, ending a 50-year wait for a championship timesofindia.indiatimes.com+13en.wikipedia.org+13sports.yahoo.com+13.
Following that triumph, Holiday joined Boston in 2023. His veteran leadership and defensive versatility contributed heavily to the Celtics’ 2024 championship m.facebook.com+15talksport.com+15reuters.com+15. Across the Finals, he didn’t just defend opposing stars; he played pivotal moments at both ends—critical threes, timely steals, disciplined rotations—making him an unsung hero and, in many eyes, a legitimate Hall-of-Fame candidate .
Caldwell‑Pope’s journey also started in 2020 with a Lakers team that proved dominance in the Disney “bubble.” As one of the few bona fide 3-and-D wings, he brought both perimeter scoring and on-ball defense. Though the bubble championship was unconventional, Caldwell‑Pope never doubted its legitimacy—and neither should fans. He defended it forcefully, arguing that all teams played under the same conditions and that the Lakers were dominant long before the bubble setup cbssports.com+4lakersnation.com+4sbnation.com+4.
After one Lakers ring, Caldwell‑Pope moved on to Denver in 2022 and again became a key contributor on a title-contending team. In the 2023 Finals, he hit clutch shots, guarded effectively, and secured the rebound that iced the Nuggets’ first-ever championship . His steady hand and veteran presence made a notable difference on a team loaded with superstars like Nikola Jokić and Jamal Murray. Still, “KCP” was one of the unsung heroes—the silent contributors whose two-way play unlocked the team’s ceiling.
Alex Caruso’s path offers a more dramatic arc. Undrafted in 2016, he clawed his way into the league via the G‑League, eventually earning a two-way contract with the Lakers in 2017 en.wikipedia.org. By 2020, he was starting Game 6 of the Finals and contributing key minutes behind LeBron James and Anthony Davis . But controversy followed when, after winning his second ring with Oklahoma City in 2025, he quipped, “now I got a real one,” seemingly casting doubt on the bubble championship timesofindia.indiatimes.com+4as.com+4cbssports.com+4. Fans reacted strongly, and Caruso later clarified his comments were sarcastic and fueled by post-victory celebrations facebook.com+4sbnation.com+4cbssports.com+4.
Regardless, Caruso’s performance in 2025 was emphatic. He averaged 7.1 points, nearly 3 rebounds, and 2.5 assists per game, while cementing his lockdown identity throughout the playoffs . In Game 7, he recorded a Finals-high 17 steals, the third-highest ever in a Finals series reddit.com. His presence helped Oklahoma City secure its first title since relocating, cementing his status as a two-time champion by age 31.
Examining their career arcs reveals overlapping themes and divergent paths. All three share a defensive-first mindset, but their roles adapt to team needs. Holiday morphed from primary ball-handler with Milwaukee into a steady veteran stabilizer in Boston. Caldwell‑Pope transitioned from rotational wing to trusted veteran in multiple systems. Caruso moved from fringe roster player to starter, and ultimately to veteran mentor on a youthful Thunder squad.
Their championship achievements also bookend different eras of the decade. Holiday’s first title came amid pandemic-related upheaval in 2021; Caldwell‑Pope’s bubble run was in the midst of 2020’s shutdown; Caruso’s titles span both contexts, with his second coming in a fully reopened, pre-pandemic league . Each ring carries distinct narratives and obstacles—travel restrictions, locker room protocols, shifting team rosters—accentuating their adaptability and toughness.
The fact that no other player has yet matched this feat reinforces the value of “3-and-D” specialists. In an era where star power often towers, championship contention still depends on role players who deliver defensive rotation, reliable spacing, and acute situational awareness. As Reddit users have noted of these three:
“Alex Caruso joins Jrue Holiday and Kentavious Caldwell‑Pope as the only players to win at least two championships in the 2020’s, all of which won one chip with two different teams” facebook.com+4reddit.com+4facebook.com+4
“All ELITE role players” reddit.com
The emergence of this trio suggests a blueprint for modern contenders: combine superstar-led offenses with backbone role players who bring defense, energy, and veteran metal. And unlike high-scoring specialists, their value isn’t tied solely to shot-making—they bring left-on-the-table defensive possessions and championship hustle.
With half the decade to go, the question becomes: Will another player join this group? Could one of them secure a third ring? Holiday, at age 35 in 2025, remains active and productive; Caruso, too, is still a key rotation piece; Caldwell‑Pope, though moved to Memphis for the 2025 season, continues to serve as a veteran presence on playoff-aspiring teams . Their landscapes are changing, but their value doesn’t fade.
Yet, their most enduring legacy might not be the trophies themselves. It’s the implicit reminder that championships aren’t built solely on mega-stars—they’re built on balance. Holiday’s presence allowed Giannis Antetokounmpo to be Giannis in the 2021 Bucks. Caldwell‑Pope’s defense and spacing unlocked Jokić’s offense in Denver. Caruso’s gritty play helped anchor Oklahoma City’s transition into a title contender alongside Shai Gilgeous‑Alexander.
For young players dreaming of rings, this trio offers a practical pathway: hone defense, shoot threes with consistency, remain open to changing roles, and embrace the grind. Not every player is a franchise face, but every franchise face needs the players behind them. Holiday, Caldwell‑Pope, and Caruso embody that principle.
Their shared accomplishment reminds us of the unseen labor behind the limelight—the structural reinforcement that transforms dominant finals teams into dynasties. They are not generational superstars, but they are generationally important. And that might just be the greatest story of all: that in an age obsessed with box scores and social media fame, the championship is won as much in contested catches and rotations as it is in highlight dunks.
Looking ahead, if there is a fourth player—perhaps another 3-and-D veteran—he’ll have to maintain peak health, find the right roster fit, and rise to the moment. But for now, these three stand alone. Their rings tell one story. Their consistency, adaptability, and defensive will tell another—a story about what truly matters in basketball’s most crucial moments.
In summation, Jrue Holiday, Kentavious Caldwell‑Pope, and Alex Caruso each earned two championships in the 2020s—and each went about it differently but with overlapping ingredients: defense, toughness, veteran smarts. Their rings came via different routes and teammates, but they share a common truth: in this era, championship success depends as much on role execution and defensive commitment as superstar brilliance. These three not only stood beside legends—they helped build them.
