It's a lot easier to get hired back (as a contractor or not) with a former employer with which you have a good and established relationship. The contractor already knows the dev team, already knows the kind of games they make, already has experience with the franchise, pipeline, tools, and workflow so there's very little ramp-up time. If the cost of contracting the leader's company for the work is reasonable and within the game's budget, there's little to be lost by hiring them on. This also helps establish legitimacy for the lead's contracting company - having a list of established and satisfied clients looks good to other potential clients, which makes it easier for the contracting company to get hired by other companies in the future.
Contracting at that level also pays a lot more than a salary job working for the studio. A lot of things are open for negotiation when it's company to company, including a percentage of the game's revenues. In many ways, it allows the contracting company to change the risk - reward ratio. The contractor can also take on more risk (e.g. less money paid up front) for more reward (a larger cut of the game revenue once it ships). Masahiro Sakurai of Sora Ltd. does this - he takes no money up front and gets paid entirely based on how well the game he contracted on sells.
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