Bentley was a fringe player when he was at Arsenal, outside of loan spells. AFAIK, Sidwell was nowhere near the first team.
Pretty sure Bentley left just because he wanted first team football. AFAIK, Sidwell just left because he wasn't good enough.
I think it depends on whether a player's a fringe player or a reserve player and whether that player is ambitious (Bentley) or comfortable (O'Shea).
If a player is still a fringe player by 24 or 25, then he ought to be looking elsewhere if he wants first team football.
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