For people who don't want to search ... From our friends at Wikipedia. I didn't know what it meant either, but it's freaking hilarious
"You're with me, leather" is a pick-up line reportedly used by ESPN anchor Chris Berman in Scottsdale, Arizona, in the mid-1990s, according to an anecdote submitted by a reader of the sports website Deadspin and made popular on the site after it was posted on Deadspin on April 11, 2006.[1]
Origin
According to the story, an anonymous contributor, whom Deadspin editor Will Leitch calls "a respected journalist," was flirting in a bar with an attractive woman wearing leather pants. However, his efforts proved unsuccessful when Berman, who was in Scottsdale to cover baseball spring training, walked by and told the woman "You're with me, leather." The woman immediately got up and left the bar with Berman.[2]
Berman's reaction
The relationship between Berman and the woman is unknown, although he was married with two children at the time of the story. While Berman has not publicly commented on the story, he allegedly responded angrily when he was asked whether he had ever visited Deadspin by a 15-year-old fan during the 2006 NFL Draft, where he hosted ESPN's coverage. Berman reportedly told the fan, "Why would I go and do that? That is such a stupid question. What are you, stupid? That is so stupid." [3]
This response was referenced in a June 19, 2006 column by DJ Gallo of ESPN.com Page 2. In a fictional diary entry of golfer Phil Mickelson at the 2006 US Open, Gallo wrote, "But I can't believe I got a double bogey on 18. Why would I go and do that? That is so stupid. What am I, stupid? I am so stupid." [4]