One rambling answer about being a "celebrity child" to a question about injections led directly to a jury finding him guilty of obstruction of justice.
On Wednesday, weeks after voters overwhelmingly rejected his Hall of Fame candidacy, his lawyers will argue for votes of a different kind that are just as important to his legacy.
The Major League Baseball career leader in homeruns is asking the 9th U.S. Circuit Court of Appeals to toss out his felony conviction.
Prosecutors will square off in a San Francisco courtroom first thing in the morning with Bonds' lawyers, led by San Francisco appellate specialist Dennis Riordan, who also served as part of Bonds' all-star legal team during his three-week trial that ended in April 2011.
Bonds' lawyers claim his answer was not material to the grand jury that was investigating the illegal distribution of performance-enhancing drugs, that the answer was truthful but unresponsive and that Bonds answered a similar question later in his testimony.
Prosecutors argue in their court papers that the answer was "intentionally false, misleading or evasive" and urge the judges to respect the jury's verdict.
The former San Francisco Giant and Pittsburgh Pirate was asked whether Greg Anderson, his personal trainer, ever gave him "anything that required a syringe to inject yourself with?"
Bonds referred to his father, major leaguer Bobby Bonds, when he responded "that's what keeps our friendship. You know, I am sorry, but that - you know, that - I was a celebrity child, not just in baseball by my own instincts. I became a celebrity child with a famous father. I just don't get into other people's business because of my father's situation, you see ..."
Jurors who deadlocked on three other perjury charges said after rendering their verdict that they believed that answer was meant to mislead the grand jury. Prosecutors later dropped the perjury charges and U.S. District Judge Susan Illston sentenced Bonds to 30 days house arrest and two years of probation, which she suspended pending the appeal.
Legal experts who have followed the case closely since his grand jury appearance in December 2003 are divided over Bonds' chances before Judges Mary Schroeder, Michael Daly Hawkins and Mary Murguia, each of whom were appointed by a different Democrat president and all of whom are based in Phoenix, home of San Francisco's division rival Diamondbacks and about a 20-minute drive from the Giants' Scottsdale spring training facility.
One set of analysts argue that appellate courts are reluctant to overturn jury verdicts absent an overwhelmingly obvious mistake. They say that the trial court judge, U.S. District Judge Susan Illston, is a respected jurist who has few of her cases overturned.
"There is a definite overriding respect of a jury's verdict," said Howard Wasserman, a Florida International University law professor. "Typically, it's pretty hard to get a jury's verdict reversed."
On the other hand, there are those lawyers who argue that Bonds stands a good chance to clear his name.
"The government's biggest hurdle is that testimony obstruction cases are usually based on blatant, undeniable lies to questions at the heart of an investigation," said William Keane, a San Francisco criminal defense attorney. "Here the prosecution limps in with only a single rambling, unresponsive, unimportant answer that is literally true."
Regardless of the outcome, University of New Hampshire law professor Michael McCann contends that the case was ultimately a loss of the U.S. Department of Justice.
"The main thrust of the government's original case was that he lied when he denied taking steroids," said McCann, who also edits the popular Sports Law Blog. "That's not what he was convicted of. Obstruction was not the main charge."