Damian Lillard and Jrue Holiday are both 24 years old and they are both starting PG's on teams in the Western Conference playoffs. That's about the only two things they have in common. Holiday has been injured for most of the last two seasons and he shares the ball with Eric Gordon and Tyreke Evans when he is on the floor. Lillard is a two-time All-Star who dominates the ball, racks up big stats and has made a number of game-winning shots. Holiday is in the middle of a 4-year $40 million deal while Lillard is almost certain to receive a max contract in the off-season. The fine folks at ESPN NBA Rank had Lillard as the #16 player in the whole league and Holiday checking in at #73. We're talking a difference in kind, not degree.
It wasn't always like that. Coming out of high school, Holiday was one of the most sought after players in the country. Yahoo had him as the No. 2 player in his high school class, behind only BJ Mullens. He played in Los Angeles and wound up signing with UCLA, the latest in a long line of elite PG recruits for Ben Howland, who was coming off three straight Final Four appearances. Lillard was a two-star recruit from Oakland who wasn't ranked by most of the services and who wound up signing to Weber State. Rivals gave him the generic picture on his profile page. They ranked 35 PG's in the class of 2008 and they still didn't have Lillard on the list.
As a freshman, Holiday played off the ball next to Darren Collison, not getting the chance to put up the type of stats expected out of most one-and-done freshman. Nevertheless, the glimpses of his physical tools at UCLA, as well as all the recruiting hype, meant he had no problem securing a spot in the first round. He probably would have benefited from another year of school but there was a lot of speculation that he was tired of Ben Howland's more restrictive half-court offense and that he just wanted to leave as soon as he could. He wound up being the 5th PG taken in a first round that featured 11 - Ricky Rubio, Johnny Flynn, Steph Curry, Brandon Jennings, Holiday, Ty Lawson, Jeff Teague, Eric Maynor, Collison, Rodrigue Beaubois and Toney Douglas. There was no reason to pay much attention to him in the NBA unless you had already been following him from high school.
It was a much slower build to the NBA for Lillard. He averaged 11 points as a freshman and 20 points as a sophomore, which would have been enough to get him into the first round if he had been playing in a bigger conference. Playing in the Big Sky, missing the NCAA Tournament and never playing on national TV meant there was almost no buzz for Lillard when it came to the draft. He wound up staying all four seasons of college and put up absolutely ridiculous numbers as a senior - 24 points, 5 rebounds and 4 assists on 47% shooting. Those numbers are a pretty good indication that Lillard was overqualified to still be in college but there are a lot of conferences out there and those are the type of numbers you have to put up to get noticed that far out of the beaten path.
While Lillard was toiling in the NCAA's, Holiday was gradually growing into a bigger role for the Philadelphia 76ers. He averaged 8 points a game as a 19-year old rookie before getting to 14 points in his second and third seasons. He was one of a number of guys - Andre Iguodala, Lou Williams, Evan Turner, Thad Young and Elton Brand - sharing the ball on a Philadelphia 76ers team that made it out of the first round once, when they were the 8 seed and they beat the Chicago Bulls after Derrick Rose tore his knee for the first time. They were a lot like the latest version of the Toronto Raptors and Holiday's role was similar to Terrence Ross - a young guy who was just one of the guys on an average to decent team.
After four years at Weber State for Lillard and three relatively uneventful years in Philly for Holiday, they both had a breakthrough in 2013. Lillard was drafted at No. 6 by the Portland Trail Blazers while the 76ers decided to blow up their team, shipping off Iguodala as part of a package for Andrew Bynum. Holiday wound up making the All-Star team at 22, averaging 18 points and 8 assists a game on 43% shooting, by far the best numbers of his career. However, without Bynum and with only Evan Turner still there for Holiday to lean on, the 76ers slipped into the middle of a pretty bad pack in the Eastern Conference. Lillard, meanwhile, averaged 19 points and 6.5 assists on 43% shooting as a rookie, playing well enough to even beat out Anthony Davis (3 years younger) for Rookie of the Year. After all those years in the shadow, things took a quick turn for Lillard.
All that time in school meant Lillard was ready to play a huge role right away and he walked into the perfect situation in Portland. He wasn't a young guy being asked to find his way on a team full of young guys - he was playing with proven two-way players at SG (Wes Matthews), SF (Nic Batum) and PF (LaMarcus Aldridge). LMA gave him a post-up guy he could spot-up off and a stretch 4 who could open up driving lanes while Matthews and Batum both spread the floor and covered for him on defense. When Portland brought in Robin Lopez, they had a core of older two-way veterans at every position around their young PG. Just as important, Matthews, Batum and RoLo could all impact the game without holding the ball so Lillard was given free reign to shoot as much as necessary.
Holiday was forced to play a much smaller role on a 76ers team with veterans who A) weren't as good as the Portland guys and B) needed the ball in their hands a lot more. Things only got worse when he wound up in New Orleans, where he shares a backcourt with Eric Gordon and Tyreke Evans, two guys who need a lot of shots, minutes and touches. When healthy, Holiday averaged 14 points and 7 assists a game on 45% shooting and that's about all you could expect for a PG who has to play with Gordon and Evans. There just aren't as many shots to go around in New Orleans and if Dame were playing for the Pels he would have to change his game in order to find a way to help his team win.
On the court, the biggest difference between the two players is that Holiday is considered one of the best on-ball defenders in the NBA while the Trail Blazers hide Lillard on D. At 6'4 210 with a 6'7 wingspan, Holiday is an elite athlete with long arms and great size for his position, capable of matching up with all three perimeter spots. He did a good job of switching and sliding between a number of different players in the Warriors series, which was far more competitive than the outcome would suggest. Lillard played great against the Rockets in last year's first round, when he could hide on Patrick Beverley, a defensive specialist. When they faced the Spurs in the 2nd round, his inability to keep his man in front of him was one of the main reasons for the Blazers undoing, as they couldn't hide him at the 1 (Tony Parker), the 2 (Manu Ginobili) or the 3 (Kawhi Leonard). It has been the same story in this year's playoffs - Mike Conley was destroying Dame before being knocked with a facial injury.
Here's the real problem when comparing any two guys in the NBA, even ones who play the same position. Even with all the advanced statistics out there, there's no real way to isolate the differences between the actual ability of the players and the role they have on their respective teams. The archetypal example of this is Chris Bosh vs. Kevin Love. Bosh was the 3rd option on a Miami team built around LeBron and Wade while Love was the 1rst option on a Minnesota team built around him. Love had the better statistics (which you would expect) and Bosh had more team success (which you would expect). You put Love as a 3rd option in Cleveland move Bosh becomes the main guy in Miami and it's a whole different situation. Did they really change all that much as players in the meantime? Or was the difference in their stats really just a matter of the roles they had?
If you put Holiday in Lillard's shoes in Portland, you would probably end up redistributing a few possessions away from PG and moving them on to lower-efficiency guys. The upside of doing this is you would have a much more qualified on-ball defender - the trio of Holiday, Matthews and Batum would be absolutely murder on opposing teams who are trying to initiate offense with 1-on-1 moves off the dribble on the perimeter. If you put Lillard in Holiday's shoes in New Orleans, you would have more guys hoisting 3's off the dribble and you might end up with a few fights between Lillard, Gordon and Evans about who gets to dominate the ball and who has to spend time spotting up in the corner. On the other side of the ball, a Pels defense that could barely keep itself together would have nowhere to hide Dame.
A guy whose pretty good on offense and is great on defense can be more valuable than a guy who is great on offense and average at best on defense. Basketball is played on both sides of the floor and good two-way players are the key to winning games in the playoffs. Jrue Holiday may not put up huge statistics in New Orleans but he's a guy without any glaring holes in his game so his presence in any five-man line-up instantly makes that group more capable of floor spacing, defending, passing, ball-handling and shot creating. Lillard can improve a team on offense but he has to be hidden on defense and he's definitely not helping you on both sides of the ball. That may not always come across in the regular season when he's playing next to Matthews and Batum but that has been an issue for Portland in the playoffs and it will be until Dame decides to really commit himself to defense.
At the end of the day, it's all hypotheticals. It doesn't really matter whether Jrue Holiday is a better two-way player than Damian Lillard since there's zero chance either of their teams will be deciding between the two of them at any point in the near future. For the most part, they are two ships passing at night, playing different roles on teams at different stages in the competitive cycle and only facing each other a limited number of times in a season depending on the vagaries of the NBA schedule. There is only time where that scenario would really matter and that's if Portland and New Orleans faced each other in a playoff series. Then you would start breaking down the match-ups and it would be about whether Holiday can guard Lillard better than he can guard him and vice versa.
As long as Anthony Davis stays in New Orleans and LaMarcus Aldridge stays in Portland, you would expect both teams to be perennial contenders in the Western Conference. If LMA leaves, Lillard faces the first real crisis of his NBA career and he will have to become a much better player just to keep Portland where they are, much less improve them. Holiday has had to play the background while Davis has been developing over the last two seasons, but maybe the roles for Holiday and Lillard switch once again, with a bad Portland team fading from national view while New Orleans is playing classic playoff series every year. The main thing for Holiday is staying healthy - he's going to be playing with Anthony Davis in his prime so he's going to get a lot of chances to go 1-on-1 with other PG's in a seven-game series.
Those individual match-ups are what makes the playoffs great and that's really where I think basketball separates itself from most of the other major team sports. I have to guard you and you have to guard me. That doesn't happen in football. The batter doesn't get to try to strike the pitcher out in baseball. The goalie doesn't get to slap shots back at the other goal in hockey. When two players at the same position are going 1-on-1, it doesn't matter who has the bigger shoe deal or who has been in more TV commercials. It don't matter who has the most money, who has the bigger national reputation or who has done more in the NBA. It doesn't even really matter what their statistics are against everyone else. Mike Conley vs. Damian Lillard has been pretty one-sided in these playoffs. Maybe Holiday vs. Lillard would look like that or maybe it wouldn't. After as many as 7 straight games going at one another, we'd have a pretty good idea of who the better basketball player was.