Leitch: And it’s been seven since the playoffs. Whereas in baseball, we practically expect to win.
Wulf: The Yankees have an awful lot to do with that. But everybody else has chipped in.
Leiter: I was on the other end of the 2000 World Series, as a Met, and I remember I desperately wanted the Yankees to beat Seattle, even though I knew it would be a tougher matchup, because I wanted to be part of a Subway Series.
Wulf: It’s so much harder for the Yankees to win now than in the past.
Leiter: No player movement, no free agency … So, if you look at his numbers and what he’s going to accomplish as a New York player, I want to talk about Derek Jeter. He’s here fifteen years—he’ll be the only player to ever, from start to finish, get 3,000-plus hits with the Yankees and surpass Lou Gehrig. His numbers aside from home runs are off the chart. He’s a champion. He’s a captain. He is an athlete. Babe Ruth had a lot of home runs, but it’s hard for me to imagine that chubby man running down a line drive to right center field. Making a dive to play. So I’m thinking about athleticism.
Wulf: I used to have this argument with Tim Kurkjian all the time, that the modern player is so much better than the old-time player. If you put Candy Maldonado in a time machine, he would hit 61 homers in 1927.
Leiter: Whether it’s fair or not, I see this big mammoth man that was overmatching everybody else like LeBron does. I’m with you on the impact: He saved the game, basically, from a time when the attendance was really poor.
Sheehan: They had to build a stadium that could hold 70,000 people.
Leiter: Whereas, with Joe DiMaggio, I’ve seen footage of him gliding through center field—if his career hadn’t been cut short, it might be him. So, instead of choosing Babe Ruth, I side with Willie Mays. Even though he’s only here in New York for eight years, he was, at that time and still to this day, talked about.
Wulf: I told my boss what I was doing this afternoon. He said, you’re going to vote for Willie Mays, right? I said he’s right up there but there’s somebody else I have in mind that I really want to push. An I told him the name and he said, “wow, that’s interesting.” I find myself siding with a guy with one of the most incredible careers in baseball history, and his entire life is contained within 25 miles of New York City. That’s Lou Gehrig. He went to Columbia. He was from Yorkville. He spent his entire life here. He played more games than anybody else consecutively. He did it as a Yankee. And I know this sounds silly, but whenever somebody imitates Lou Gehrig’s farewell speech, the thing that they miss is that he has a New York accent. That to me is the winning touch. He was the greatest athlete the Yankees may have seen.
Sheehan: If you’re going to weight some sort of New York heritage, I think it does push Gehrig up into the discussion. But Gehrig played his career in the shadow of Babe Ruth—up until 1934, he was basically second to Babe Ruth, not just in terms of performance but because of who they were as a person, and that carries a lot of weight to me 75 or 80 years later.
Wulf: It’s almost as if Babe Ruth was of the world and Gehrig was of New York. Plus Gehrig embodies all those other qualities of New York that we sometimes overlook. You know, the workaday athlete who goes to the ballpark and does incredible things and is often overlooked.
Leitch: Nobody ever overlooks Derek Jeter.
Sheehan: I think Derek Jeter is more beloved than even Yogi Berra was. You want to compare them at 35, I think Jeter is more beloved at 36 than Berra was at 36. A lot of Yogi’s legend is post–playing days: becoming the manager, getting fired, ending up with the Mets. Is Derek Jeter going to be Mickey Mantle, where he stays in the public eye and opens a restaurant and almost has a second career down the road? Or is he going to disappear and become a recluse like Joe DiMaggio did, other than the Mr. Coffee and the—
Leiter: I think he’d be more inclined to do that.
Sheehan: With Jeter, you have the whole stats-versus-guys-within-the-game thing. Is he a good defender? Is he a bad defender? Is he such a bad defender that he’s a bad player? I’ve been having these arguments for fifteen years about Derek Jeter. You forget that, even if he’s a bad defense or shortstop, he’s still one of the 30 greatest players in baseball history. And the championships do matter. If the Pirates took Derek Jeter in that draft, we wouldn’t be having this conversation, but they didn’t, the Yankees did. This guy is a first- ballot Hall of Famer.