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The Yankees won a Word Series in 1998 — their second in three seasons and the start of a four-in-five reign — and Jeter had his first All-Star season, batting .324 with a league-leading 127 runs, 19 homers, 84 RBI and 30 steals. Kelly was wrapping up her time on “Friday Night Lights” and was named Esquire’s Sexiest Woman Alive.HANNAH DAVIS DENIES THE DEREK JETER 'GIFT BASKET' RUMOR Before Davis, Kelly was the odds-on favorite to finally get Jeter to settle down. Jeter and the Yankees won a World Series in 2009, Kelly was along for the ride as he approached 3,000 hits — a milestone he reached with a home run in 2011 with Kelly in attendance at the Stadium — and continued to pile up All-Star Game appearances.Carey was already a huge star when she and Jeter became an item, and the two-year relationship proved fruitful for the young shortstop.
With this being March, the time is right for a tournament-style showdown between the lovely ladies the Captain has cozied up to. It’s a bit of a May-December romance with these two, who are separated by 16 years — she’s 25 and he’s 41.
Minnillo, the MTV VJ, was the first long-term public relationship Jeter had with the Yankees, dating from 2003 to 2005.