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First things first: let's define honorable for this article. When I use the term "least honorable", I'm referring entirely to their contributions towards the Chargers winning football games / championships. At no point will I be referring to their off-the-field problems/contributions, their moral character, or anything else that could be perceived as "honorable".
I'm only interested in establishing who the most and least deserving members of the Chargers' Ring of Honor are, based entirely on their playing careers with the Chargers. With no further ado...
The Inaugural Class
The first time the Chargers inducted players into their Ring of Honor was 1976, when they inducted Emil Karas, Frank Buncom, Bob Laraba, and Jacque MacKinnon. All four players were inducted posthumously which, coupled with the fact that it was the inaugural induction class, likely lowered the bar of what the Chargers considered for induction.
While MacKinnon and Buncom's contributions are borderline-worthy, two of them fall woefully short based on production alone:
Bob Laraba
Bob Laraba played linebacker for the Chargers in 1960 and 1961. He was tragically killed in an automobile accident following the 1961 season at the age of just 28.
Laraba's career highlights include punting (in addition to linebacking) for the Chargers in that 1960 season, as well as two pick-sixes in the 1961 season. That said, 28 games makes him the Chargers' Ring of Honor player with the least playing time as a Charger. In fact, his career AV ranks just 290th on the Chargers career list. I understand his induction, though, due to the circumstances.
Emil Karas
As previously mentioned, Karas was inducted posthumously, having died of pancreatic cancer in 1974 at the age of 40. Karas played in 60 games as a Chargers linebacker over 6 seasons, four as a full-time starter from 1960-1963.
Karas's career AV of 37 gives him a robust per-game figure, but both his games played and career AV are behind several Chargers linebackers who haven't made the Ring of Honor, like Woodrow Lowe, Billy Ray Smith, and Gary Plummer.
Ed White
Ed White, a guard, was traded to the Chargers from Minnesota in 1978 on the heels of three consecutive Pro Bowl seasons. White would end up playing 8 seasons for the Chargers, starting 117 games, but making just one Pro Bowl as he played out the end of his prime and his twilight years entirely for the Coryell era.
While Ed White has been called the best offensive lineman of his era by teammates, and Dan Fouts adamantly believes he's a Hall of Famer, Ed White is much more of a Viking than he ever was a Charger. In fact, White played in every Vikings Super Bowl.
In Chargers context, there are several offensive linemen that aren't in the Chargers' Ring of Honor with more games played and carAV than White: Billy Shields (who played on many of the same teams as White) is the most notable, though several recent players (Kris Dielman and Nick Hardwick) can boast the same thing. Based on how much time White spent outside the organization helping another team win, and that his performance (both anecdotal and empirical) was better prior to being a Charger, I think White's inclusion in the Chargers' Ring of Honor is debatable.
Stan Humphries
I'm sure many of you will disagree with this, but let's be honest: Stan Humphries is only a member of the Chargers' Ring of Honor because he was the quarterback when the Chargers defense took them to went to the Super Bowl.
His numbers certainly don't justify his induction on their own: of the eight quarterbacks -- Dan Fouts, Philip Rivers, John Hadl, Drew Brees, Jack Kemp, Doug Flutie are the others -- in the Chargers' top 200 carAV leaderboard, Humphries ranks dead last on a per-game basis. He threw 73 picks in 76 starts as a Charger with a QB rating below 80.
And let's dismiss the idea that Humphries was clutch right now: Humphries had a 6/13 TD/INT ratio in the postseason, including two 4 INT performances in the '93 and '95 playoffs. The Chargers lost both those games.
I used to boast that Humphries was the best Chargers' QB of all-time (measured solely by Super Bowls they led the Chargers to), but even I must admit that Humphries's numbers don't justify his spot in the Chargers' Ring of Honor.
Darren Bennett
He's a punter. That be enough for some of you, but for the rest I'll delve deeper into the numbers.
I'm sure some of the younger crowd here believes that Bennett spent an eternity in San Diego as he started his career a Charger and played here until he was 38 (and is still an active member of the Chargers community). However, that would be forgetting that Bennett didn't come to the NFL until the age of 30, so he actually spent less than a decade on the football field for the Chargers. In fact, Mike Scifres has now played exactly as many games as a Charger, 144, as Bennett.
It wasn't like Bennett was the most dominating player in the world, either; while he was certainly good, he only led the league in punting once, made one All-Pro team, and went to the Pro Bowl twice. (A personal annoyance: Bennett never once succeeded on a fake punt attempt.)
Finally, Bennett punted for some real bad football teams; the Chargers were only over .500 once in Bennett's career: his rookie season. Certainly, as both a punter and a member of bad teams, Bennett wasn't significantly contributing "towards the Chargers winning football games / championships", like I defined above.