As the years go by, we are entering the 20th season of our Rewritten Rings simulation, and with it comes a new reality: more and more players are beginning to enter the league, build their legacies, and eventually retire.
But Isiah Thomas is not one of them. Thomas entered the NBA in 1981, two years before our simulation began, and by the time we reached the 1983-84 season, his star had already been firmly established.
He had been an All-Star as a rookie and repeated the accomplishment in Year 2. In fact, in his real-life career, Thomas would go on to make the All-Star team in 12 of his 13 seasons. But in Rewritten Rings, his story would last much longer—and take a dramatically different path.
The first major change came almost immediately. In real life, Thomas and the Pistons were eliminated by the Knicks in the opening round of the 1984 playoffs.
In our world, Detroit went much further, with Thomas leading the Pistons all the way to the Eastern Conference Finals in our very first season. Unfortunately, that would be as far as he could take them. Detroit fell to Larry Bird and the Celtics, beginning what would become a recurring theme of Thomas' career: getting close to the top without quite reaching it.
The following season brought another deep run, but another disappointment, as Detroit lost to Philadelphia in the Conference Semifinals.
Then came three consecutive first-round exits. The contrast with Thomas' real-life career during this stretch is fascinating. The 1985 and 1986 seasons played out similarly in both worlds, with a Conference Semifinals loss followed by a first-round defeat.
But in 1987, the paths dramatically diverged. In real life, Thomas finally reached his first Conference Finals and once again found Larry Bird's Celtics waiting for him. In Rewritten Rings, he had already reached that stage three years earlier—and had already learned what it was like to fall short against Boston.
Then came 1988, perhaps one of the biggest examples of how differently Thomas' legacy developed in our universe. While Thomas and Detroit suffered another first-round exit, the real-life Pistons were beginning their run of three consecutive NBA Finals appearances, eventually winning two championships in three years. The Bad Boys became one of the defining teams of the late 1980s. That simply isn't the story we tell here.
Instead, Thomas left Detroit.
After three disappointing seasons with the Pistons, Thomas signed with the Seattle SuperSonics, joining a young Len Bias. The move immediately produced results.
In his first season in Seattle, Thomas helped Bias capture his first league MVP, while the Sonics advanced all the way to the Conference Finals. But there was a massive “what if?” hanging over that playoff run.
Bias was injured and unable to play, and Seattle was swept by Karl Malone and the Rockets. How different might that series have been if Seattle's newly crowned MVP had been healthy?
We will never know.
Thomas and the Sonics wouldn't get that close again. Seattle ran into Houston in each of the next two seasons, losing in the Conference Semifinals both times.
Then, in 1991, Bias left Seattle and signed with Thomas' former team in Detroit. The impact was immediate. In his first season with the Pistons, Bias led Detroit all the way to the NBA Finals. But once again, the Rockets stood in the way, and Bias ultimately suffered the same fate with Detroit that he had with Seattle.
With Bias gone, Thomas moved on again.
In 1992, he signed with the Portland Trail Blazers, giving him yet another chance to chase the championship that had continued to elude him. His first two seasons in Portland produced an unusual split against Magic Johnson and the Lakers.
Thomas helped Portland win their first-round matchup with Los Angeles in 1992, but the Lakers got their revenge the following year. Then, in 1994, Thomas accomplished something few players in NBA history could claim: he led three different franchises to the Conference Finals. This time, however, Hakeem Olajuwon's Los Angeles Clippers ended Portland's run.
At this point, you had to wonder: was Thomas ever going to get over the hump?
The next two seasons did little to answer that question. Portland suffered consecutive first-round exits, and at 35 years old, Thomas' window appeared to be closing. In real life, his career had already been over for a few years. But this is Rewritten Rings, and Thomas wasn't done yet.
The 1996 offseason brought one final gamble. Portland traded away its first-round draft pick for an aging Brad Daugherty, and somehow, the move paid off.
With Daugherty providing another piece for the veteran Trail Blazers, Thomas finally reached the NBA Finals at 36 years old, three seasons after he would have retired in real life.
It was an incredible achievement—but unfortunately for Thomas, the destination was a nightmare.
Waiting on the other side was Shaquille O'Neal and the defending champion Orlando Magic. Portland never stood a chance, as Orlando swept the Trail Blazers and ended Thomas' first—and only—appearance in the NBA Finals.
Thomas would never return to the Finals, never win an NBA championship, and never experience the ultimate team accomplishment that had defined his real-life career. He finally retired following the 2001 season, having extended his career seven seasons beyond his real-life retirement.
That extra longevity did produce another accomplishment: Thomas finished his Rewritten Rings career with 14 All-Star selections, two more than he earned in real life. But would he really trade those two additional All-Star appearances for the two championships he won in reality? It's hard to imagine otherwise.
And that's what makes Thomas' Rewritten Rings career so fascinating. His résumé is undeniably impressive. He played for three different franchises, took all three to the Conference Finals, reached an NBA Finals at an age when he would have been retired in reality, earned 14 All-Star selections, and ultimately received the game's highest individual honor with a place in the Basketball Hall of Fame.
His impact was also recognized by the franchises he helped build, as both Detroit and Portland retired his iconic No. 11 jersey, cementing his place in the history of two organizations despite never bringing either an NBA championship in our universe.
Perhaps that's the strangest part of Thomas' alternate history. In reality, he is remembered as the leader of the Bad Boys and a two-time NBA champion. In Rewritten Rings, he had the longevity, the individual accolades, and the deep playoff runs—but never got the championship moment.
So now I'm turning the question over to you.
Have you been following Thomas' journey through the simulation? Do you think he should have won a championship? If so, when was his best opportunity—and which team should have gotten him over the finish line?
Seattle with a healthy Len Bias? Portland with Brad Daugherty? Or was there simply never a season where the pieces came together for Thomas?
Let me know in the comments.
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