Chauncey Billups may not always be mentioned alongside the greatest players of his era, but the five-time All-Star and 2004 Finals MVP holds a remarkable achievement that no one else in NBA history can claim. Billups is the only player with a winning record against Michael Jordan, Kobe Bryant, and LeBron James, three of the game’s most iconic legends.
6-4 vs. Michael Jordan
Billups went 6-4 against Jordan across his career, splitting those matchups between Jordan’s time with the Chicago Bulls and his comeback years with the Washington Wizards.
Individually, Jordan still produced against him, averaging 25.1 points, 7.1 rebounds, and 3.5 assists in those contests. Billups, meanwhile, averaged a respectable 13.3 points, 3.1 rebounds, and 4.0 assists.
What’s notable is that Billups faced Jordan at very different stages, first during the Bulls’ dynasty years, then again in Jordan’s final run. Even so, Billups walked away with a winning record, something few guards from that era can boast.
24-21 vs. Kobe Bryant
Billups’ most memorable head-to-head battles came against Kobe Bryant. Across 45 meetings, Billups went 24-21, including a narrow edge in both regular season (18-16) and playoffs (6-5).
Statistically, Bryant had the upper hand, averaging 25.9 points, 4.8 rebounds, and 4.8 assists. Billups countered with 17.3 points, 2.9 rebounds, and 5.3 assists, often serving as the floor general who steadied his team.
Their most famous clash came in the 2004 NBA Finals, when Billups led the Detroit Pistons to a stunning upset over the heavily favored Los Angeles Lakers.
In that series, Billups earned Finals MVP honors after outplaying not only Bryant but also a roster that featured Shaquille O’Neal, Karl Malone, and Gary Payton. It remains one of the defining moments of his career and a legacy-defining battle against one of the game’s fiercest competitors.
22-17 vs. LeBron James
Billups also has the distinction of holding a 22-17 record against LeBron James. In regular-season matchups, Billups was particularly successful, going 16-10. However, in the playoffs, James got the better of him with a 7-6 edge.
Head-to-head, James’ numbers were as dominant as ever: 25.5 points, 7.4 rebounds, and 6.7 assists. Billups, though not matching the raw stats, was effective with 14.6 points, 3.3 rebounds, and 5.8 assists.
Their most memorable clash came in the mid-2000s when Billups’ Pistons regularly stood in the way of LeBron’s Cavaliers.
In the 2007 Eastern Conference Finals, James delivered his iconic Game 5 performance, scoring 48 points, including Cleveland’s final 25 points in double overtime, to finally topple the Pistons and push through to his first NBA Finals.
Billups’ rare distinction speaks to more than just numbers, it reflects his consistency, leadership, and ability to elevate his teams against all-time greats.
While Jordan, Kobe, and LeBron each left behind mountains of accolades, Billups carved out a legacy of his own.
Being the lone player with a winning record against three of basketball’s greatest icons is a testament to Billups’ competitive fire and his reputation as “Mr. Big Shot.” He may not have had the flashiest game, but his record against legends cements his place in NBA history.
