What Michael Jordan’s 1995 playoff loss taught trainer Tim Grover about winning
Key Takeaways
- •Tim Grover, who trained Michael Jordan and Kobe Bryant, founded the Chicago-based company Attack Athletics in 1989 and now markets his winning philosophy through books, podcasts, and online platforms.
- •Grover's 2013 book 'Relentless' categorizes competitors into three tiers—Coolers, Closers, and Cleaners—with Cleaners defined as those who deliver results no matter what obstacles they face.
- •Grover's online training platform, The Relentless System, costs $599 for lifetime access, and his newer series, Breakthrough, covers ten themes including obsession, pressure, and fear and doubt.
- •Grover frequently cites Jordan's elimination by the Orlando Magic in the 1995 playoffs, after which Jordan resumed training immediately and the Bulls swept Orlando en route to three consecutive titles from 1996 to 1998.
- •A 2024 Fortune commentary criticized the leadership style portrayed in 'The Last Dance,' warning that leaders who display flaws with pride may teach others that abrasive behavior is the price of success.

The Orlando Magic had just eliminated the Chicago Bulls from the 1995 playoffs, and much of the criticism focused on Michael Jordan. When Jordan’s trainer, Tim Grover, told him he would see him later, Jordan did not wait for a schedule. “I’ll see you tomorrow,” he replied, according to Grover’s later account to Sports Illustrated.
That instinct—to lose and return the next morning—is central to the philosophy Grover now sells. The CEO of Attack Athletics, the Chicago-based training company he founded in 1989, has turned decades of work with Jordan, Kobe Bryant and other NBA stars into books, an online training platform and a message for executives that treats winning as a discipline.
Business leaders have long borrowed lessons from sports. Fortune has profiled CEOs who credit high school athletics with building the discipline and accountability they bring to the boardroom. Grover’s output now spans books, podcast appearances and a paid online platform aimed at that same audience. His approach is more demanding, and it comes with a price tag.
Coolers, Closers and Cleaners
Grover’s framework begins with his 2013 book, Relentless: From Good to Great to Unstoppable, written with Shari Lesser Wenk. The book divides competitors into three categories, described in terms familiar to managers.
Coolers are dependable but unremarkable. “The individual that shows up at 9:00 and leaves at 5:00…their work is okay,” Grover said on The Art of Charm podcast. They complete what they are asked to do, but little more.
Closers perform well when the conditions are clear. “The closer can deliver the end result as long as too many variables are not thrown at them,” Grover said. Give them a plan and they will execute it.
Cleaners occupy the highest tier. Grover defines a Cleaner as “an individual that’s going to get you that end result no matter what’s thrown at them.”
His 2021 follow-up, Winning: The Unforgiving Race to Greatness, published by Scribner, returns to the same hierarchy. “But there is one thing all Cleaners have in common: the ability to achieve the end result over and over,” he writes.
A $599 course based on the books
The same categories form the foundation of The Relentless System, Grover’s online training platform. The program costs $599 for lifetime access and includes a module titled “Are you a cleaner?” as well as lessons called “Don’t Think” and “Decide. Commit. Act. Succeed. Repeat.” Buyers also receive a guide identifying which of the three types they are.
A newer online series, Breakthrough, is structured around 10 themes, including obsession, pressure, and fear and doubt. Grover presents the material as a call to action rather than reflection.
“I don’t teach mindset,” Grover says in a video on his website. “It’s too many thoughts, ideas in your head that have you overthinking with no action.”
Why Grover returns to The Last Dance
Much of Grover’s material draws on The Last Dance, ESPN’s 2020 docuseries about the Bulls’ final championship season. The series became ESPN’s most-watched documentary ever, airing in spring 2020 when the COVID-19 pandemic had suspended most live sports, while Netflix distributed it internationally. Fortune also covered the production and its global reach in a 2020 report.
Episode 8 revisits the 1995 playoff series. Jordan had returned from baseball that spring, after a 17-month retirement spent with minor-league baseball’s Birmingham Barons, and the Magic, led by Shaquille O’Neal and Penny Hardaway, eliminated the Bulls in six games in the Eastern Conference semifinals.
Hardaway later said the victory had backfired. “The respect was always there, but my thing was you had to attack him before he attacked us. But all we did was piss him off,” he told Sports Illustrated. The following season, the Bulls swept Orlando in the Eastern Conference finals on their way to the title—the first of three consecutive championships from 1996 through 1998—as documented in another Sports Illustrated account.
In Winning, Grover quotes Jordan defending how hard he pushed his teammates during that period: “Look, I don’t have to do this. I’m only doing it because it is who I am. That’s how I played the game. That was my mentality.”
That mentality has also drawn criticism. A 2024 Fortune commentary on “the rise of the jerk” described the Jordan portrayed in The Last Dance as “Petty. Mean. Kind of angry.” It warned that leaders who display their flaws with pride can teach others that being a jerk is the price of success. The back-and-forth is a reminder that importing lessons from elite sport into management remains contested terrain. Fortune has separately examined how sports behavior influences workplace culture in its coverage of Travis Kelce and the rise of “jerk” culture.
Grover emphasizes the other side of the story. For him, the lesson of 1995 was not the loss itself, but what Jordan said next.
This story was originally featured on Fortune.com.