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Contract year looming for up to 42 Cowboys; Re-sign early or wait and see?

When the Cowboys decided to pick up the fifth-year option on Tyler Smith’s contract a week ago, they ensured their 2022 first-round pick would not hit unrestricted free agency in 2026.

That decision dropped the total number of players playing on expiring contracts this year to 41. But then the team went out and traded for George Pickens, who is playing on an expiring contract, bringing the total back up to 42.

All of which places the Cowboys front office in somewhat of a conundrum: extend those players now and hope to get a great performance on the cheap, or wait until those players break out before re-signing them and risk overpaying in the process?