Gray broke the news in a live interview on ESPN with
Los Angeles Rams running back, and single season rushing record holder,
Eric Dickerson, on being traded from the Rams to the
Indianapolis Colts on October 31, 1987. The interview was hailed by ESPN anchor
Tom Mees as, "The night ESPN SportsCenter truly arrived and was born. We have now gone from a highlight service and interviews to a legitimate news gathering and breaking news operation." On March 22, 1989, Gray got an exclusive, a television interview with NFL Commissioner
Pete Rozelle in
Palm Springs, California when Rozelle suddenly decided to retire. On October 5, 1993, during Game 1 of the
1993 American League Championship Series between the
Chicago White Sox and
Toronto Blue Jays, Gray reported
Chicago Bulls minority owner
Eddie Einhorn told him
Michael Jordan would retire from the Chicago Bulls the next day. Jordan was in attendance at the game with Einhorn. Gray followed Jordan out of the stadium to the parking lot with a camera crew and Jordan acknowledging and confirming to Gray what Einhorn told him was true and that Jordan would retire. During Game 4 of the 1996 NBA Eastern Conference Finals, Gray interviewed Leonard Armato,
Shaquille O'Neal's agent, while the game was going on with questions about the future of Shaquille O'Neal and then head coach
Brian Hill. After a series of tough questions, Gray ended the interview by saying to Armato, "Try to enjoy the game now that you've been grilled!" The interview served as a platform for O'Neal and set the stage as a month later O'Neal left the Magic and signed with the Lakers. During the
1997 NBA Finals, Gray interviewed
Dennis Rodman during an
NBA on NBC segment. After repeatedly questioning Rodman about his comments about the
Mormon religion when (the
Chicago Bulls were in Salt Lake City to play the
Jazz during the Finals), Rodman finally had enough of the questions, walked off the interview set with tears in his eyes and removed the microphone without assistance. NBC showed the ending of the interview as it happened during the NBA Finals pre-game show. On June 24, 2000, in
Glasgow, Scotland, Gray interviewed Mike Tyson after his swift knockout of
Lou Savarese where Tyson proclaimed he "wanted to eat his (
Lennox Lewis') children." Gray has been known for his close relationship with
Kobe Bryant, which showed in the immediate aftermath of Bryant's
sexual assault case (the night when the news broke, Gray appeared on
SportsCenter in defense of Bryant's character) and in several sideline interviews. It was Gray whom Bryant called to vent about teammate
Shaquille O'Neal in October of that year (a phone call that started one of O'Neal and Bryant's
worst disagreements). Gray's interviews with maligned baseball player
Barry Bonds in 2006 and 2007 were the only one-on-one interviews Bonds granted after breaking both Babe Ruth's and Hank Aaron's home run records. In both interviews, he denied using steroids or other performance-enhancing drugs. On July 8, 2010, Gray interviewed
LeBron James when he revealed his 2010 decision to sign with the
Miami Heat as a free agent on a live ESPN special called
The Decision. On May 7, 2015, Gray interviewed
New England Patriots quarterback and 4 time Super Bowl champion Tom Brady at
Salem State University in
Salem,
Massachusetts regarding Brady's involvement and the Patriots role in
Deflategate. It was the same day the NFL announced the results of the Wells Report. It is the only one-on-one interview that Brady has done on the subject. On August 27, 2017, Gray interviewed
Floyd Mayweather in the ring after his victory against
Conor McGregor at which time Mayweather officially retired from boxing with a record of 50–0. Mayweather joined other boxing legends and champions
Larry Holmes (April 1995) and Mike Tyson (June 2005) by announcing their retirements from boxing while in the ring during questioning by Gray. On April 30, 2018, Gray interviewed Brady in Los Angeles. In response to a question whether if the Patriots had the appropriate gratitude for his achievements, Brady replied, "I plead the fifth.” The most notable interview of Gray's sportscasting career occurred with former
baseball player Pete Rose. During Game 2 of the
1999 World Series, Rose was introduced as a member of the
Major League Baseball All-Century Team. After the ceremony, Gray (who was covering the series for
NBC) asked Rose about the
Dowd Report's allegations that he had gambled on major league baseball games, which he repeatedly denied:
Jim Gray: Pete, let me ask you now. It seems as though there is an opening, the American public is very forgiving. Are you willing to show
contrition, admit that you bet on baseball and make some sort of apology to that effect?
Pete Rose: Not at all, Jim. I'm not going to admit to something that didn't happen. I know you're getting tired of hearing me say that. But I appreciate the ovation. I appreciate the American fans voting me on the All-Century Team. I'm just a small part of a big deal tonight.
Gray: With the overwhelming evidence in that report, why not make that step...
Rose: No. This is too much of a festive night to worry about that because I don't know what evidence you're talking about. I mean, show it to me...
Gray: Well, the Dowd Report says- but we don't want to debate that, Pete.
Rose: Well, why not? Why do we want to believe everything he says?
Gray: You signed a paper acknowledging the ban. Why did you sign it if you didn't agree with it?
Rose: It also says I can apply for reinstatement after one year, if you remember correctly. In the press conference, as a matter of fact, my statement was "I can't wait for my little girl to be a year old so I can apply for reinstatement". At my press conference. So you forgot to add that clause that was in there.
Gray: Well, you have reapplied. ... You've applied for reinstatement in 1997. Have you heard back from
Commissioner Selig?
Rose: No, and that kind of surprises me. It's only been two years, though, and he's got a lot of things on his mind. But I hope to some day.
Gray: Pete, it's been 10 years since you've been allowed on the field. Obviously, the approach that you have taken has not worked. Why not, at this point, take a different approach?
Rose: Well, when you say it hadn't worked, what do you exactly mean?
Gray: You're not allowed in baseball. You're not allowed to earn a living in the game you love. And you're not allowed to be in the
Hall of Fame.
Rose: Well, I took that approach and that was to apply for reinstatement. I hope Bud Selig considers that and gives me an opportunity. I won't need a third chance. All I need is a second chance.
Gray: Pete, those who will hear this tonight will say you have been your own worst enemy and continue to be. How do you respond to that?
Rose: In what way are you talking about?
Gray: By not acknowledging what seems to be overwhelming evidence.
Rose: Yeah, I'm surprised you're bombarding me like this. I mean I'm doing an interview with you on a great night, a great occasion, a great ovation. Everybody seems to be in a good mood. And you're bringing up something that happened 10 years ago.
Gray: I'm bringing it up because I think people would like to see ... Pete, we've got to go, we've got a game.
Rose: This is a prosecutor's brief, not an interview, and I'm very surprised at you. I am, really.
Gray: Some would be surprised that you didn't take the opportunity. After conducting the interview, Gray offered no apology for his line of questioning toward Rose: I stand by it, and I think it was absolutely a proper line of questioning. . . I don't have an agenda against Pete Rose . . . Pete was the one who started asking me questions. I definitely wouldn't have gone (that) direction if he had backed off. My intent was to give Pete an opportunity to address issues that have kept him out of baseball. I thought he might have had a change of heart. . . . He hadn't had an opening in 10 years. . . . If I had let that go, all of you (reporters) would have had me on here today for a totally different reason. However, after the fallout of heavy criticism toward him & NBC that ensued from the interview, Gray offered the following apology on-air prior to the start of Game 3: (I) thought it was important to ask Pete Rose if this was the right moment for him to make an apology. If in doing so the interview went on too long and took some of the joy of the occasion, then I want to say to baseball fans everywhere that I am very sorry about this. Despite Gray's pre-game apology,
New York Yankees outfielder Chad Curtis snubbed Gray's request for an on-field interview with him right after hitting the game-winning
walk-off home run:
Jim Gray: Tell us about that pitch.
Chad Curtis: I can't do it. As a team, we kind of decided, because of what happened with Pete, we're not going to talk out here on the field. Curtis claimed it was a team decision not to speak with Gray, but Yankee manager
Joe Torre later suggested that Curtis had acted independently. On January 8, 2004, more than four years after the interview, Rose's autobiography
My Prison Without Bars was published. In the book, Rose finally admitted publicly to betting on baseball games. ==Personal life==