Indianapolis Colts owner Jim Irsay is a complicated man - a man of contradictions.

Enigmatic, fabulously wealthy and a prolific tweeter, Irsay would often reach out to help those in need - donating generously to local charities and businesses or assisting individuals, often offering direct support.

But Irsay also has a history of keeping at arm's length those he purported to love the most.

Kimberly Wundrum, a woman that Irsay lived with on and off for nearly a decade, was not just his girlfriend, not quite his wife. Irsay bought her three homes during their time together, he gave her a diamond ring - which she referred to as an engagement ring - and would write her love notes, friends said.

But when she died on March 2, 2014 of a drug overdose in the condo that Irsay had purchased for her - a year since their relationship had ended, a year since Irsay had met another woman and had Kim removed from the home they shared - he did not appear at her funeral or viewing, instead sending a bouquet of blue orchids in the shape of a horseshoe in his stead.

It was only nine days later that Irsay was pulled over by police and a bag of pill bottles was discovered in the front seat of his SUV along with $29,000 in his briefcase. He was arrested and charged with four felony drug counts.

It wasn't Irsay's first brush with addiction - or the police.

In 1995, then the GM of the Colts, Irsay's name was unearthed by Indianapolis police detective Irene Conder in the files of a doctor who was suspected of running a pill mill - Irsay was not alleged to have broken any laws.

Two years later, at age 37, Irsay became the youngest owner in the NFL after his father, Robert, died from heart failure. The Colts selected Peyton Manning in the 1998 draft and Irsay and the city of Indianapolis renegotiated the lease for the RCA Dome, assuring the franchise would stay put for at least 10 more years.

Irsay's star had begun to shine brightly in NFL circles.

But again, his name surfaced in connection with doctors illegally overprescribing pills. Detective Conder told the Indianapolis Star at the time, "I could not get [Irsay] identified as the guy who picked up the pills from the pharmacy, and prosecutors would not charge him without a positive identification."

Despite the lack of charges, Irsay got the message and sought help at Sober Life Alternatives, an Indianapolis addiction treatment center. What could have been an embarrassing scenario seemed only to further ingratiate Irsay into the fabric of Indianapolis life and culture.

But four years later, in 2002, just as he was trying to rebuild the Colts in the new AFC South, The Indianapolis Star reported his third and most serious brush with the law.

Federal drug agents who were bearing down on a prominent plastic surgeon discovered that Irsay had received a staggering 120 prescriptions over the course of a year - from Lorcet and Vicoprofen to Xanax and the anti-panic drug Klonopin. In one alarming 24-day binge, the paper reported, he was prescribed 400 tablets of the painkiller Oxycontin.

Again, Irsay avoided charges. But this time, his public reputation took a hit. The story became front page news, with local television station WTHR reporting that Irsay had at least three overdoses in the past.

He released this statement after the incident: "This summer I sought professional help at a nationally recognized facility located outside Indiana. I have successfully dealt with my dependence and my chronic pain issues. I ask that my privacy and that of my family be respected on this health issue."

Meanwhile, Kim Wundrum had moved to Florida and was developing a romantic relationship with an unhinged attorney who was paying her to watch his children and abused the same drugs as his clients.

Kim began doing drugs as well.

In October 2002 she was pulled over with a dozen Xanax and 105 Oxycodone pills in an unlabeled prescription bottle in the center console of her Toyota.

Her mother brought her back to Indianapolis, where Kim did her best to regain control of her life. Her sister Rhonda, a masseuse who had Jim Irsay as a client, suggested Kim as a babysitter when Irsay mentioned he needed someone to watch the children of a friend visiting his lake house in Culver, Indiana.

Kim and Jim - over conversations about their troubled pasts - hit it off right away. Things escalated quickly - especially for Irsay.

"Jim gave her rings and presents all the time," says a friend from Florida, Robyn Boback, who regularly flew to Indianapolis to visit. "[They] had a whole other life without the public."

But even as things advanced, Irsay did his best to keep a certain distance between Kim and himself - especially when it came to the public eye. Over time, the strain of this predicament affected her and she began to slip into old habits - abusing pills.

In 2010, Jim called Lauren Cohen, one of Kim's closest friends to confide that he was worried about her. He paid for Kim to go to a rehab center in Malibu.

She returned stronger, fitter.

But in the spring of 2013, after two more rehab stints for Kim and after Jim had begun a relationship with a married former bikini calendar model, things finally ended. While Kim was away at rehab, Jim had her things relocated from their home to a condo on the outskirts of Indianapolis.

Upon her return, Kim was devastated.

On Sunday, March 1st, Kim was discovered sitting upright and fully clothed in the bathroom of her new condo. The coroner would conclude that she had died of polysubstance overdose.

On March 17th, Irsay was pulled over for driving while intoxicated and discovered with the pills and money.

Since her death, Irsay has not publicly mentioned Kim's name or acknowledged her existence.

In a June interview in The Indianapolis Star with Bob Kravitz, Irsay had this to say about his arrest; "The disease aspect gets lost when you're talking about alcoholism and addiction," he said. "Even in 2014, there's still this stigma."

Irsay, upon his return to the NFL from his six-game suspension on October 10th, offered this tweet as his only public commentary:

"What can I say? I could say something, but nothing IS something; nothing isn't nothing, if I say it; it's something. No things are nothing things."

Complication or contradiction - Irsay is a man without answers.