The Day I Gave George Steinbrenner Advice

George Steinbrenner and I have two things in common. We are both alums of Williams College, 1952 and 1988 respectively, and we both love the New York Yankees.

The former brought us together in the fall of 1984.

I was a freshman at Williams then. Both my freshman roommates played football. Both were running backs. I don’t think either played all four years, but on this day, homecoming 1984, my roommate Kenny started at halfback against our arch rival Amherst.

The record shows that Williams lost that day 23-6 and that Amherst completed an undefeated season. It wasn’t until my senior year that we next beat Amherst in football, starting a streak of eight victories in a row.

I’ll remember that day, however, because that day I gave George Steinbrenner advice about the Yankees.

I had found a spot in the stands around the 40-yard line, wanting to watch Ken, rather than join the tailgaters just off the end zone at Weston Field. At the start of the first quarter, George sat down next to me.

I had been a Yankee fan since elementary school. We had no team in D.C., the Senators having left for Texas when I was 4. I didn’t like the Orioles, even though everyone said I should, because Baltimore was the closest city to us with a baseball team.  Instead, I decided to root for the Orioles’ rivals, the Yankees.

And there I was in November 1984, a Yankee fan sitting next to The Boss. An 18-year-old kid with clear opinions about his favorite baseball team had the ear of that team’s controversial owner. Way cool.

I nodded and said hello. He asked how the team was doing. I said ok, and I pointed out Kenny and told George that Kenny was my roommate. George watched and said some nice things about Kenny’s performance. He was cordial and friendly.

Steinbrenner and Winfield in 1989 – 5 Years After I Told George Not to Trade Him

Nothing else stands out in my memory until halftime. As everyone got up to go get a cocktail or beer, I said to George, “Don’t trade Dave Winfield.” (Sportswriters then were suggesting that might happen.) George chuckled and replied back, “I’ll see what I can do.”

The sports almanacs show that, indeed, Winfield was not traded from the Yankees that off-season.  The following season (1985), Winfield was an All-Star, and won a Gold Glove and Silver Slugger award. As this New York Times article from 2008 explains, Winfield and Steinbrenner would have some trying times, but finally reconciled in recent years.  As a fan, I never knew what happened behind the scenes.  I just wanted to see Winfield in right field wearing number 31 for the Yankees.

After talking to George that November day and relaying my opinion, I got to see #31 in the Yankees line-up until 1990, when he was traded to the Angels.

Rest in peace, George.

Thanks for listening. I’m glad I could help, and thanks, as a fan, for following my advice.

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