Rackauckas named him senior assistant in 1999 and chief assistant a year later in a management shake-up that led to lawsuits, resignations and a climate of fear. During this period, the Orange County Grand Jury issued a report criticizing Rackauckas for mismanaging his office. To this day, Middleton dismisses those rocky times as the result of misinformation spread by enemies of Rackauckas, "who has more integrity than any person I've ever met."
Professionally, Middleton said his proudest moment came two years ago, when he was greeted with a standing ovation from his colleagues moments after the jury returned guilty verdicts in the second trial of Gregory Haidl, Kyle Nachreiner and Keith Spann.
The sexual assault case gained notoriety because the 2002 attack of the 19-year-old accuser occurred at the home of former Orange County Assistant Sheriff Donald Haidl, and was captured on a lurid 21-minute videotape.
"You never expect anything like that -- ever," he said. "I felt embarrassed at first. But later, I thought a lot about it. It makes you realize how important these cases are. It ... tells citizens that people are going to be held accountable for what they do to women. A female cannot be treated like that, regardless of what their background is."
Middleton took over the case, clearing his calendar, nine months after jurors deadlocked in favor of acquittal in the first trial, handled by another prosecutor. In a change of legal strategy, he narrowed the charges and streamlined the testimony. And for the first time, he showed the videotape to the victim, who hadn't clearly remembered what happened to her that night.
John Barnett, a prominent defense attorney who represented Nachreiner, said it was rare for a prosecutor to take a case that had become such a wild card.
"It says a lot about him. Something positive," Barnett said. "He took a case that was on the verge of being lost, and tried it anyhow. The prosecution had the tape, but it didn't work the first time. There's obviously a danger that it might not work a second time. He displayed all the things you expect in a very good prosecutor, in his judgment, preparation and performance."
Middleton hasn't been immune from criticism. In 1994, he was in charge of the sexual assault unit when prosecutors were blamed for going light on rapists. In one case, they declined to prosecute a three-time convicted rapist accused of a fourth rape. A year later the man raped and killed a woman. Middleton was fast and forthright in providing a public explanation of the decision not to prosecute, as has been his practice.
"Is there any other way to be?" he said.
Superior Court Judge Francisco P. Briseno, the presiding judge of the Haidl case and senior bench officer in Orange County, said the one thing that has always stood out about Middleton is his integrity.
"That's the hallmark of his work and who he is," Briseno said. "He's very thorough, very conscientious, very meticulous ... a remarkable person to be around. When you see a person work under high levels of stress, you really get to see their character."
Middleton is much more laid-back at home and in social settings, according to his wife of 32 years, Dyan. And when he drops his guard, she said, he is affectionate and fun. He likes to tease and banter with their two grown children. And he's not shy about hugging his 6-foot-1 son.
"He's a hands-on dad," Dyan Middleton said. "He's the hardest working man I've ever met. But he's not a workaholic. He balances his life."
Which brings him to surfing, a favorite escape since he took up the sport while growing up in Baldwin Park. He has braved big sets at Pipeline and Makaha while stationed at a naval air base in Hawaii. These days, he prefers the slower pace of San Onofre State Beach because of the "feeling of being so far away" from everything.
"You go out and surf and it's a completely different environment," he said. "It has a very calming effect."
On a recent winter's morning, Middleton cuts a youthful figure as he checks the break at Dog Patch. Trim and compact, he is cradling a longboard. The bluffs bask in the amber glow of an early sun. Too flat to paddle out.
With him is Dave Himelson, a regular surf buddy who retired last year as a senior assistant district attorney. Himelson is amused how Middleton, meticulous and reliable, is always showered, shaved and exactly on time.
"He's so well-coiffed, and I show up looking like a sub sandwich," Himelson jokes later. "Once you get him wet, though, he looks like the rest of us. Messed-up hair and a smile on his face."
An avid gardener and woodworker, Middleton has other activities planned for his retirement. He is already at work on his latest project: remodeling his kitchen.
But starting Friday, look for him on the waves.