Veldheer had really hit his stride in his second season in Oakland. The former third round pick was one of the better left tackles in the NFL and had started 42-straight games by the end of the 2012 season. Barnes had just started finding his footing at right tackle in 2011 before going out with an injury. Suddenly those who criticized him for his penalties, were noticing just how much he was needed. He started the entirety of the 2012 season and these two made for arguably the best left tackle/right tackle combo the Raiders had had since the Barry Sims/Lincoln Kennedy bookends of the early 2000's.
2. Barry Sims, Cornell Green (2007)
One of the better tackle duos for the Raiders over the years. Though both were with the team for several years, this was the only season they both started at each tackle position as it was Sims' last with the Raiders and Green's first. The Raiders had a hell of a time replacing Sims at left tackle, going through three left tackles in three years. They had even tried moving him to guard to make way for Robert Gallery the season before and that didn't work either.
3. Barry Sims, Robert Gallery (2004-05)
While Gallery gets a lot of flak for his play at left tackle, he was fairly good at right tackle. It seems most people forget he even played there. Gallery was drafted to be the left tackle of the future but Sims was firmly entrenched as the Raiders longtime starting left tackle so there was no sense in messing with a good thing. Oh, and the very next season, they messed with a good thing and proved why they should have just left well enough alone.
There is much uncertainty in these two. Penn is coming off a season in which he gave up the second most sacks in the league (12) and Watson has barely set foot on the field after suffering several recurring injuries prior to his rookie 2013 season. Watson is said to have all the physical abilities and natural talents. But he has played just one season of Division I football so he is still raw potential. Penn is a former one-time Pro Bowler (2010) and was considered to be a pretty good left tackle prior to his horrible 2013 season. He claims his poor play was due to lingering injuries. The Buccaneers thought different and replaced him this off-season. This ranking is giving some benefit of the doubt to Penn because if Penn plays like he did last season, this duo drops in these rankings considerably. The right tackle is in good shape regardless, with Austin Howard able to step in should Watson falter.
5. Khalif Barnes, Tony Pashos (2013)
The cobbled together tackle duo of Barnes and Pashos. Barnes was supposed to continue as the starting right tackle this season but with the injury to Jared Veldheer, he was forced to the left side. Menelik Watson was supposed to be available to start on either side but he too was injured. With Barnes on the left and Watson out, the team signed Pashos off the waiver wire and implanted him as the starting right tackle. Barnes wasn't spectacular but held his own. Pashos was named the best player in the preseason for the Redskins and he continued that steady play with the Raiders.
6. Jared Veldheer, Langston Walker (2010)
It was Veldheer's rookie season. Tom Cable inexplicably started him out at center before switching him back to left tackle. Even then, he was sharing time with Mario Henderson. The jumping around had him all messed up and it took him about half to season to get settled in at left tackle. Walker was making his return to the Raiders' starting lineup after a two-year stint in Buffalo and an injury shortened 2009 campaign. He actually played fairly well. It was his last season in the NFL, allowing him to finish his NFL career in the Bay Area where it started and where he grew up.
7. Robert Gallery, Langston Walker (2006)
There's no denying that Gallery was a failure as a left tackle. This "can't miss" number two overall pick had short arms and could keep the edge rushers out of the backfield. He and Walker got a lot of hate spewed at them that season, some of which was not warranted. Once defenses figured out Aaron Brooks was a easily rattled, they sent the house. Then Andrew Walter came in and stood flat-footed, allowing defenses to plow him over. They also had an incompetent offensive coordinator who called for 5 and 7 step drops despite the pressure. It was the only season at left tackle for Gallery, who moved on to play some very good left guard. It was also Walker's last season in Oakland before heading to Buffalo where he played pretty well.
8. Mario Henderson, Cornell Green (2009)
There was a moment there where the Raiders thought they had a gem in fifth round pick, "Super" Mario Henderson. It wouldn't last. By season's end the luster was off and he was clearly not the answer. The Raiders would replace him with Jared Veldheer in the following draft. Green actually played some pretty good right tackle but it was overshadowed by Henderson's poor play.
9. Kwame Harris, Cornell Green (2008)
Poor Cornell Green. He plodded along, doing a good bit of protecting from the right side while Kwame Harris had a monumental collapse. While he wasn't letting defenders run by him, he was committing false starts because they were in his head. That season was so bad, it was Harris' last in an NFL uniform.