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Since you called him a stud, I'd sign him after his first year of arbitration eligibility. But take a close look at his development and scouting reports. Also, pay attention to his intangible attributes like greed, intelligence, work ethic, and leader ability. He might be a great ballplayer early on, but will his progression over the next few seasons warrant spending on him sooner?
Some players flame out quickly. Some are more prone to injury. Some get greedy. Some are not as loyal.
Also, if your team has enough players with higher leadership attributes, he's more likely to keep in line.
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