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The Cowboys have sent 139 players to the Pro Bowl since 1996 and have four playoff wins to show for it. This is a larger issue than roster construction alone.
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The Pro Bowl is a meaningless game that barely qualifies as football, but the title of a “Pro-Bowler” still carries weight. While the selection process isn’t perfect, it is a good indication of the best players at each position from a given season. And it is common for the Dallas Cowboys to send their fair share of participants.