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Andre Iguodala never won Sixth Man of the Year. Really think about what that means. Andre Iguodala, a future Hall of Famer, a literal Finals MVP, the defining reserve of a generation, never won Sixth Man of the Year. He lost out to such luminaries as Eric Gordon, Jamal Crawford and Lou Williams... three different times. They're all fine players. None of them are going to the Hall of Fame. They do share one trait that Iguodala lacks, though. They're all buckets.

The formula here is rather simple: 10 of the past 17 winners have led the NBA in bench scoring. Many of those who didn't finished in second. Only once in the past 20 years has a Sixth Man of the Year Winner missed the playoffs, and it was Williams, a legacy winner. I could point out the irony in voters picking winning teams and ignoring winning players like Iguodala, but we're not here to critique their process. We're here to make money off of it. 

Fortunately, those voters are so consistent that we already know what to look for. We want a high-scorer, ideally a guard, on a fairly good team. We also have to be wary of younger players who are due starting jobs. James Harden won this award in 2012 and was clearly overqualified as a reserve. Unsurprisingly, he was a starter and max player in Houston a year later. You should be extremely wary of reigning winner Tyler Herro (+500) for this exact reason. Pat Riley has publicly challenged him to earn a starting job, and he's in a contract year, so odds are he's going to do everything in his power to earn it. 

Even with Herro likely too risky to play, there are plenty of viable bets on the board. We'll start at the top of the candidate pool (pun intended for reasons that will be clear in a moment) and then work our way down.

All odds via Caesars Sportsbook

The favorite: Jordan Poole (+450)

Poole's ability to score enough for this award is not in question. He averaged over 25 points per game in Golden State's final 20 regular-season games. If he is a full-time reserve, he's either going to lead the NBA in bench scoring or come very, very close on what should be one of the league's best teams.

The real question here is whether or not Poole will remain on the bench long enough to be considered a sixth man. After all, he started during that scorching stretch to end last season. To qualify for Sixth Man of the Year, a player need only come off of the bench more times than he starts in a given season, and typically, voters have held to that standard even when it's been close. Lamar Odom, for example, won the award in 2010 despite starting 35 of 82 games. So long as we remain below the 50 percent standard, Poole should be judged on the merits of his play.

So here's the $450 question: is Jordan Poole going to come off of the bench in more than half of his games next season? I'm inclined to say yes. The risk we're running into here is that both Stephen Curry and Klay Thompson are getting older and frequently miss time due to injury. Fortunately, Steve Kerr tends to prioritize bench stability more than most coaches. Andre Iguodala has started just 21 regular-season games under Kerr. When Kevin Durant missed a month in 2017, Iguodala didn't start once. When Harrison Barnes was out for a similar timeframe during the 2015-16 season, Iguodala started just once. 

This hasn't been quite as true for Poole. He started in place of both Curry and Thompson last season, though I'd wager that had a lot to do with Moses Moody's status as a rookie. Moody's development will be a priority with Gary Payton II gone, and there's another experienced starter at shooting guard in Donte DiVincenzo also available here. Both more closely mirror Thompson's off-ball skill set and defensive traits than Poole, whose shotmaking would only be a true necessity in Curry's absence. In other words, there's some risk here, but the reward outweighs it in my eyes. I've bet on Poole and likely will continue to do so.  

The middle of the class

Some names I like:

  • Malcolm Brogdon (+1300) is going to open the year as the Sixth Man on what I expect to be the best regular-season team. Injuries and an upgrade to the starting lineup are concerns, but Brogdon has been an All-Star contender when healthy in Indiana. He's overqualified as a reserve and that will show.
  • Anfernee Simons (+2500) has proven worthy of a starting job, and his new $100 million contract certainly pays him like a starter, but Portland's lineups simply make more sense if he plays big minutes as a reserve. The Blazers should stagger Simons and Damian Lillard as much as possible, pairing Lillard with Josh Hart in the starting lineup to give them the size and defense they've long-lacked in the backcourt, while Simons makes more sense next to Gary Payton II, a lockdown defender who never needs the ball. The Blazers will run plenty of three-guard lineups, and I'd expect Simons to close games, but there's a reasonable chance Hart starts while playing fewer overall minutes. This is how James Harden won the award in 2012. He was clearly a better player than Thabo Sefolosha, but his team knew he made more sense as a reserve.
  • Tim Hardaway Jr. (+5000) finished fifth in his last healthy season. He's worth a flier if Dallas insists on starting Dinwiddie. 

Some names I dislike:

  • Cam Johnson (+2000) is a wonderful player, but a poor fit for this award. Given the offseason trade rumors surrounding Jae Crowder, who is now on an expiring contract, there is too good a chance that Johnson starts to justify a bet here. Even if he doesn't, Phoenix stands out as a strong Bojan Bogdanovic trade destination, and the two of them share somewhat redundant skill sets. Oh, and Johnson will never be the primary ball-handler even on bench units so long as Chris Paul and Devin Booker are on the roster and continue to be staggered.
  • Spencer Dinwiddie (+2500) is starting this season. Jason Kidd has said as much. Now, I'll get to why I believe that won't last when we cover MVP, but I'm sorry, there's no good reason to make a preseason Sixth Man of the Year bet on an opening night starter. You're going to see better odds than this.
  • Jordan Clarkson (+2000) is almost certainly going to be on another team. We don't know which one. If you're going to bet on him, I'd encourage you to wait out the trade market. You might lose a bit in terms of odds, but you have far more to gain in the way of certainty.

The long shots

I'm going to start by begging the sportsbooks to put up odds on Russell Westbrook. Whether it's as a Laker or following a trade and a buyout, there's a very good chance that Westbrook doesn't end this season as a starter. Westbrook literally called last season a failure because he didn't average a triple-double. We know he's going to put up numbers if he steps on the floor. If you see Westbrook odds anywhere, it's worth a couple of bucks as a flier.

Now then, onto the candidates with posted odds. Here are the few long shots I'm eyeing:

  • Dennis Schroder (+10000) finished second for this award for the 2019-20 season. He doesn't currently have a job. That's going to change, at the latest, in November or December when somebody suffers an injury. When it does, he's going to put up plenty of points off the bench. Even in what was widely considered a failed stint in Boston, he topped 14 points per game. You could make a similar but less compelling case for Carmelo Anthony (+20000).
  • Duncan Robinson (+20000) probably remains on Miami's bench with defense more of a priority now that P.J. Tucker is gone... but let's game this out. Miami has three other relatively interesting candidates: Herro, Victor Oladipo (+3000) and Max Strus (+15000). I suspect Strus retains Robinson's former starting position at small forward, and one of Herro or Oladipo starts next to Kyle Lowry at shooting guard. However, with no way of knowing who wins that starting job, neither Herro nor Oladipo looks especially enticing at their current odds, and if Lowry goes down, we could see both of them starting. So in Robinson, you're getting an almost guaranteed reserve for a contender on a $90 million contract... at 200-to-1. Yea, that's a worthwhile risk.
  • Kyle Anderson (+10000) doesn't fit our formula one bit, but hear me out. Kevin Love finished second a season ago. Joe Ingles did a year before that. George Hill and Fred VanVleet both have recent top-five finishes despite averaging single-digit points. Almost every year, a hipster candidate emerges from a surprisingly successful team. The voters who disagree with the traditional formula tend to publicly back candidates like this. They don't actually win, but they at least manage to weasel their way into the conversation enough to become strong cashout candidates. Anderson is the best reserve on a Minnesota team that should be quite good in the regular season, and after spending the past season as a linchpin of one of the NBA's best benches in Memphis, he's going to have some residual support. Bruce Brown (+7500) is another strong candidate for this slot.

Team plays

While I typically don't recommend team plays in favor of a winner, there are teams I'd advise you to stay away from:

  • The Knicks have four candidates I would love on any other team. Derrick Rose (+12500) nearly won this award two seasons ago. Evan Fournier (not on the board) is probably going to be supplanted by Quentin Grimes in the starting lineup, but fits the "scores a ton and doesn't do much else" archetype to a tee. Immanuel Quickley (+3000) and Obi Toppin (+5000) both have playing styles very favorable to this award, but they're blocked by more expensive veterans (Jalen Brunson and Julius Randle). Remember, Tom Thibodeau is New York's coach. There's not going to be enough playing time for one candidate here, let alone four. The Knicks relied on their bench a season ago, but their coach remains more committed to his starters than any other in the NBA.
  • The Clippers have more candidates than I can count, and that's precisely the point. Their lineup is going to change frequently thanks to aggressive load management schedules for Paul George and Kawhi Leonard. It's simply going to be too difficult for any single Clipper to build any narrative momentum over his teammates when they're all shuffling in and out of the opening five.
  • The Kings have too many mouths to feed. Malik Monk had a Sixth Man of the Year kind of season a year ago, but even at +7500, I'm not enticed enough to assume he's going to find shots on a roster with De'Aaron Fox, Domantas Sabonis, Kevin Huerter, Davion Mitchell, Keegan Murray, Harrison Barnes and Richaun Holmes.
  • Love finished second a season ago and Ricky Rubio had an early-season case, but I'm ignoring all Cavaliers after the Donovan Mitchell trade. If we assume Mitchell and Darius Garland are staggered, there just aren't going to be enough touches available for anyone else.