Back in 2009, Rondo's then-defending NBA champion Boston Celtics, got the better of the upstart Bulls in an epic first-round playoff series that featured seven overtimes in seven games. The bad blood from that lingered, with Rondo and Joakim Noah harboring a rivalry for years.
Between then and now, the Celtic's Big Three era ended; one of the breakout stars, then-Bulls rookie Derrick Rose, had a Hall of Fame career derailed by injuries before a trade to the New York Knicks in June; revered Celtics assistant Tom Thibodeau took over as the Bulls head coach, went on a five-year run of playoff success and was eventually driven out of town by clashes with management; and Rondo, no longer the player he was, had disappointing stints in Dallas and Sacramento.
Both Rondo and the Bulls are in very different places now than they were in 2009. However, they're at similar points in their respective stories, which is why this union makes some sense, even though it makes no sense at all on the basketball court.
After trading Rose and losing both Noah and Pau Gasol in free agency, the Bulls are in search of a new identity coming off their first lottery appearance since 2008. Rondo, once considered one of the league's elite point guards, is looking to re-establish his place and rebuild his reputation after leaving each of his last two stops on bad terms.
Years of injury-related baggage aside, the Bulls traded Rose largely because he couldn't play with Jimmy Butler. They're both ball-dominant scorers, and neither has a reliable outside shot. General manager Gar Forman said after that trade that he wanted the team to get younger and more athletic, to better suit head coach Fred Hoiberg's free-flowing offense.
Trading Rose, and not trading Butler on draft night despite a flurry of rumors, sent a clear message that they were giving the reins of the franchise to the younger guard.
And so, after all that, Forman's solution is to bring in a point guard older than Rose (Rondo will turn 31 during this coming season), with a serious knee injury of his own in his past, who isn't any more of a threat to score, can't play off the ball under any circumstance and is a much more questionable personality fit than Rose?
Rondo has butted heads with coaches at his last two NBA stops, to the point where he was essentially exiled from the Mavericks locker room in the middle of the 2015 playoffs.
After last year's rocky introductory period for Hoiberg—including an infamous December incident when Butler told reporters he needed to coach the team harder—the last thing the Bulls need is to introduce a personality that could make it harder for Hoiberg to get his locker room on the same page.
Rondo's clashes with Mavericks coach Rick Carlisle largely stemmed from disagreements over play-calling responsibilities. Hoiberg will give Rondo more freedom, but that may not sit well with Butler, who was very vocal heading into last season about wanting to run more of the offense.
As imperfect as Butler's fit was with Rose, it was at least workable because both of them could play off the ball.
Rondo has to be quarterbacking the offense and setting up other players for offense, or he becomes a massive liability. His respectable 37 percent shooting from three-point range last season with the Kings was an outlier—the first time in his career that he hit above 32 percent and just the fourth time he broke 30. Mostly, he gets the Tony Allen treatment on offense: Teams don't bother guarding him, daring him to shoot because they know he won't make them pay.
Even Rondo's league-leading 11.7 assists per game feel like empty stat-padding given the lack of results they produced for the 33-win Kings.
Once an elite defender at the point guard position, Rondo now gambles too much for steals and actually admitted in early 2015 that he " played defense in a couple years." This is a problem considering the defensive liability of many of the Bulls' other rotation players—Doug McDermott, Nikola Mirotic, rookie Denzel Valentine, and basically every wing except Butler.
But bad basketball fit aside, the Bulls-Rondo marriage feels off because it signifies a lack of direction for the organization. Trading Rose and letting Gasol and Noah walk made sense because this group of past-their-prime veterans had run its course, and it was time to build around Butler by going young.
Bringing in another past-his-prime veteran with a strong personality and a history of not getting along with coaches runs counter to that vision. It feels like saving face, trying to tread water without taking any meaningful steps forward.
The Bulls are clearly bothered by missing the playoffs last season and don't want a repeat. Rondo doesn't make them much better, but last year's 42 wins might be enough in the Eastern Conference.
Still, it's hard to look at the move and feel it gets them any closer to relevance in either the short or long term.