Season 5 of Arrow has gotten off to a busy start. In addition to sporting some new all-weather duds in his vigilante alter ego, Oliver has taken time out as mayor of Star City and its protector to recruit an all-new Team Arrow. Meanwhile, new Big Bads Tobias Church and the mysterious Prometheus have both made themselves known in different ways, with the former launching an all out offensive to try and kill the Green Arrow once and for all. Meanwhile, the latter has been restricted mostly to a few violent encounters around the city. In other words, there’s been a lot on the plate of Star City’s savior, and it doesn’t look as though things will be getting any easier anytime soon.

At the end of last week’s ‘A Matter of Trust‘, Oliver learned that John Diggle had wound up in prison. Obviously, trusting his friend means this isn’t something that Oliver can let stand. As such, the next episode, ‘Penance’, will take the Green Arrow and (maybe) the rest of Team Arrow 2.0 into the concrete corridors of a government correctional facility to spring John Diggle and hopefully get to the bottom of why he was incarcerated in the first place. It’s the sort of engagement that will not only test the new team’s mettle, but it will also give Diggle and Oliver a chance to be reunite in person.

A new extended trailer for the episode along with some recently released stills show that while Oliver is committed to springing Diggle from the pokey, ‘Penance’ has more up its sleeve than a run-of-the-mill prison break. Because nothing on Arrow can be that simple, it would appear Ollie’s new recruits take issue with his plan to free Digg and attempt to stop him. The trailer shows a brief throwdown between Oliver and Curtis, Rene, and Evelyn, who apparently have learned very little since spending an episode getting kicked in the face trying to ring a bell. Although it can’t possibly end well for the recruits, the insubordination continues to make for an interesting dynamic between Oliver and his new team. The original Team Arrow clashed with Ollie plenty, but the team was built on a solid foundation that went beyond their masks and suggested the disagreements would eventually sort themselves out. That’s not the case here, as Oliver’s ties to the new team beyond busting crimes with them are tenuous at best.

Adding to the sense of conflict is Diggle and Oliver’s relationship that underwent more than its fair share of speed bumps in the last two seasons. Still reeling in season 4 from Oliver using Lyla in his season 3 dealings with Ra’s al Ghul, the two eventually made nice but the classic Digg/Oliver dynamic has never felt quite the same. Perhaps this prison break will be what the duo needs to rekindle the old magic and to get John back to doing what he does best.

If this is indeed Arrow’s way of bringing Diggle back into the fold of the main storyline, it likely couldn’t have come at a better time. The trailer also shows Tobias Church has a heavy presence in the episode, meaning the formidable gangster might be stepping up his campaign against the Green Arrow. If this is indeed the case, then it will put Church at odds with Prometheus, which may finally bring the masked villain out from the shadows and into a more direct and confrontational role with Oliver.

Arrow continues this Wednesday with ‘Penance’ @8pm on The CW.

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