And on this night, after Jeter reluctantly exited a victory over the Red Sox hobbled by a bone bruise of his left ankle, Jeter smiled into the crosshairs. How much did it hurt? How long had it hurt? Most importantly, how much time would it cost the Yankees without their captain and leadoff hitter?
In hindsight, we should have known the answers. Jeter has given them before, and they never seem to change.
"It's like I say, I don't talk about injuries," Jeter said. "Either you play or you don't. I'm playing, so it's not an issue. At this point in the season, I'm sure there are a lot of guys that have some things bothering them. I'm really never one to talk about them."
Sure enough, as promised, Jeter was back in the lineup the next night -- equaling Willie Mays on baseball's all-time hits list, no less. Back in New York, Jeter played all three games of a weekend series against the Rays and has seen four straight contests as a designated hitter heading into Monday's much-needed off-day.
Jeter has alternated between saying that he feels "great" and "fine," and neither Yankees manager Joe Girardi nor general manager Brian Cashman are buying it. But they also wouldn't expect to hear any different from Jeter, and at this crucial point in the schedule, they should be thankful for that.
"We're not better without him in the lineup," Cashman said. "The only way you have to look at it is Joe and the medical staff have to decide here and there, because we're playing not just to get to October -- we want to play all the way through October having everybody as healthy as they can be. That's the goal."
Girardi has allowed himself a few moments -- like the snapshot when Jeter limped alongside Andruw Jones to the team bus in Boston, or his increasingly frequent visits to head athletic trainer Steve Donohue's office -- to consider exactly how the Yanks can pull this off without Jeter in the batting order.
"We'd have to find a way," Girardi said, not so convincingly, "but we've all seen what he's done this year. He's been our leadoff guy all year. I started thinking about it: if he wasn't able to play, who was I going to lead off? There's a lot of questions that go through your head when you think that."
Pressed for his options, Girardi suggests that Jayson Nix, Nick Swisher, Russell Martin or Eduardo Nunez could serve as leadoff hitters if Jeter disappeared.
"So I hope he plays," Girardi said.
Jeter hasn't appeared at shortstop since that night in Boston, with Nunez offering mixed results in his place. And Jeter's return to the field may be delayed after Girardi again spotted "a little limp" in Jeter's step on Sunday.
Girardi has said that he sees the injury more when Jeter runs the bases. Of course, Jeter is also spending more time than most on the basepaths; he owns a Major League-leading 199 hits this season and an active 12-game hitting streak.
That all means that as Jeter heads into the months for which he is known best, he'll probably be playing with some level of discomfort. Bone bruises don't heal overnight. Luckily for the Yankees, Jeter appears to be able to tolerate more than most.
"I mean, that's a big part of it for him," second baseman Robinson Cano said. "That's a guy who plays hurt. That tells you how much he cares about this team and how much he loves this game, you know."
The Yanks would love to be in position to offer Jeter a few days to rest and get healthy for the postseason, but the Orioles aren't exactly going along with that plan.
"If we want to help Derek Jeter, we have to win as many games as we can so we can rest Derek Jeter," Cashman said. "But Derek Jeter will tell you, 'If you want to help me, shut up, write my name in the lineup and let me get my hits and help us win.'"
Cashman knows that chilly tone quite well; the 2010 offseason wasn't fun for either party, as Cashman and Jeter slugged it out on the back pages, with the GM telling Jeter's party to "shop it" if they thought anyone would top the Yankees' contract offer.
Dredging up 2010 now seems like almost ancient history. But don't doubt that Jeter was keeping score while some were preparing his career obituaries; that criticism seems to have fueled Jeter's motivation.
"I hit .270, man. You know? Sorry," Jeter said. "One time I hit .270, and it's like it was the end of my career. You're going to struggle, you're going to have good years, you're going to have bad years. But you always have to have confidence that you can play.
"I think every player probably at some point in their careers had a year where they weren't satisfied. I had a lot more than just one that I haven't been satisfied with. I know that year has gotten a lot of attention, but you still have to have confidence that you can play."
The roles have been reversed; now, the chatter revolves around Jeter's candidacy for the American League Most Valuable Player Award. He'll be in the discussion, certainly, but an award doesn't appear to be in his future. Jeter shakes his head when asked if his career is incomplete without an AL MVP Award.
Individual honors are nice, as Jeter has always said, but the reason you go through this - preseason workouts, Spring Training defensive drills, thousands of hours in the batting cage and, yes, playing through nagging injuries -- is to finish the year on top.
"Winning the World Series. I mean, that's it," Jeter said. "I tell you that all the time. I'm being honest with you when I say it. That's what we play for, to win a championship. We try to do that each and every year, so that's what's satisfying."