By Thomas Gerbasi, photo by Tom Casino/Showtime

It was probably the one conversation Lou DiBella didn’t think he would ever be having, at least not about Jermain Taylor. But it was going to be a necessary chat where the answer would determine where the relationship between promoter and fighter stood.

“Here’s what I want to know,” said DiBella to one of the specialists that had checked out Taylor, a former middleweight champion attempting a comeback after two years off from a sport that had seen him lose four of his last five bouts, three by knockout. “If this was your kid, would you let him fight?”

“No,” said the doctor. “I wouldn’t let my kid fight, period. But if you’re asking me if I would let this man fight vis a vis the level of risk versus any other athlete who gets in the ring and participates in a combat sport, I can’t tell you that there’s any reason why this man can’t fight and at any greater risk than anybody else.”

DiBella accepted the answer, like he accepted the others he received from the Mayo and Cleveland Clinics, as well as the Nevada State Athletic Commission, which voted 5-0 in favor of licensing Taylor in October.

Two years earlier, in December of 2009, DiBella resigned his post as his first world champion’s promoter, not wanting to see the Arkansas native risk his health in the ring after suffering a scary knockout at the hands of Arthur Abraham on October 17, 2009.

“I walked away from a number of other fighters, and I’ve released fighters who I knew still had some economic value and wound up fighting for other promoters because I just felt in my gut that the time had come for them to call it a day,” DiBella told BoxingScene. “It’s not an easy decision, and ultimately, you gotta live with yourself. You gotta look in the mirror. This is often referred to as a hurt business, and it’s an unforgiving business. And when it’s unforgiving in the sense of a bad decision that costs a guy his economic career, that’s unfortunate and terrible; but when it’s unforgiving in the sense of a guy that’s never the same mentally or emotionally or psychologically, or dies young like the Quarrys and leaves family behind, that’s tragic. If I could avoid a tragedy for a few bucks, it doesn’t make me Mother Teresa to do that. It doesn’t make me a great guy to do that; it’s just the right thing to do.”

It was, and you can say what you want about DiBella or about boxing promoters, but if you have been around the sport for any length of time, the one thing that characterizes DiBella is that he cares. If you’re ever on the receiving end of one of his outbursts you may wonder what it is he cares about, but his emotional attachment to the sport and his tendency to wear his heart on his sleeve is preferable to dealing with an ice cold businessman who only sees the fighters and the sport as numbers on a spreadsheet. So when DiBella resigned as Taylor’s promoter, it was a gut wrenching decision that still made all the sense in the world. Thankfully, Taylor stayed on the sidelines, and while he didn’t say he was retiring, in early 2010 he said he was taking a rest from the sport.

Earlier this year, “Bad Intentions,” clean bill of health in his hand, was done resting. His advisor, Al Haymon, remained on board, his original trainer, Pat Burns, returned to the fold. All that was left was for Taylor to get a promoter, and while DiBella was the obvious choice, the New Yorker wasn’t going to jump back in without exhaustively questioning everyone involved first. Eventually, he got the answers he needed.

“I’ve seen reports from multiple hospitals, multiple clinics, and multiple specialists,” he said. “I’ve seen unanimous votes from state athletic commissions, and I personally got clearance from Jermain to speak to a few of the doctors. The one thing that was very clear to me was that most of the doctors agree that he’s not at any greater risk than any other fighter. Additionally, it was clear to me, as was evidenced by Nevada, that he’s gonna be licensed and he’s gonna fight. I also believe that his advisor, Haymon, cares about him. I watched him operate through this process and I know that he cares about the kid, and I also know that I do. I think that provides similar levels of checks and balances.”

Tonight, at the Morongo Casino Resort & Spa in Cabazon, California, the 33-year old Taylor makes his return to the ring against 22-2-3 Jessie Nicklow. Unless Taylor has completely faded from his championship form, it should be a fight he wins, and in the process, will be a fight that won’t tell us much about where he’s at athletically circa 2011. No one knows this better than DiBella, but he’s still aware that certain tells will signify whether this comeback is going to go well or be an immediate disaster.

“I know that beating Jessie Nicklow, if that’s what he does on Friday night, doesn’t mean he’s ready for Sergio Martinez,” said DiBella. “He (Taylor) has had multiple years off, and he needs a fight or two beyond that fight, before he moves on to a higher level of opposition. And if he looks like s**t against Jesse Nicklow or gets hit an inordinate number of times, that’s gonna say certain things. Now I tend to believe he’s gonna look really good. I knew that he had issues before he walked away. I think he had tasted the high life, he had tasted big success and big money for the first time, and he was doing things and living a lifestyle that he hadn’t lived previously that wasn’t in the best interest of his boxing career. His training wasn’t what it should have been, his partying was a lot more extensive than it should have been, and he wasn’t the same Jermain I knew when he turned pro.”

In 2001, DiBella – fresh from his job at HBO and into his new gig as promoter - turned Taylor and a host of fellow 2000 Olympians (Ricardo Williams Jr., Clarence Vinson, Michael Bennett, Jose Navarro, Jerson Ravelo, and Paolo Vidoz) pro on the same night in Madison Square Garden. It was expected that the group would produce multiple world championships, but it was only the quiet kid from Little Rock who nabbed gold, stunning Bernard Hopkins in 2005 to win the world middleweight title.

Taylor would duplicate his win over Hopkins in their rematch, draw with Winky Wright, and successfully defend his title two more times with wins over Kassim Ouma and Cory Spinks before getting upset by Kelly Pavlik in September of 2007. It was a bout he seemingly had won, as he hurt and dropped Pavlik before getting stopped himself in seventh round, but a second loss to “The Ghost,” this one by decision proved that the first defeat was no fluke.

A solid, but uninspiring win over his 2000 US Olympic team buddy Jeff Lacy followed in November of 2008, but then came the back-to-back knockout defeats against Carl Froch and Abraham, leading to calls from all corners for his retirement. The way DiBella sees it, while the endings of both fights left no doubts, there is plenty to speculate about when it comes to the way Taylor prepared for each of his last two bouts and what ultimately happened before the final blows landed.

“The Froch fight, he clearly ran out of gas, and I think his lifestyle and training had everything to do with that fight,” he said. “The Abraham fight was a two-fold thing, and I think there still may have been issues with the training, but the bigger issue there was that I think his self-confidence was down after the couple previous fights, and I think that in Germany, Abraham’s just a different fighter. You’re not allowed to go to his body, and every time Jermain hit him with a body shot, he got a warning. Abraham’s a beast in Germany because the referees are on his side, so as soon as Jermain had to start headhunting against a guy who’s a devastating puncher, he left himself open and he got caught a few times. I actually think that if that fight would have been in the United States, even on that particular night, I think you might have seen a different fight. But it doesn’t change the reality, and he’s the first one to say this. He wasn’t giving himself the best opportunity to win, and he wasn’t his best self the last couple years of his activity.”

Having musical chairs in his corner didn’t help, with Burns being replaced after the Hopkins fights by Emanuel Steward for a four fight stint, and then Taylor’s longtime mentor Ozell Nelson coming in to man the ship for the next four bouts. But now Burns, a trainer known for his intensity in the gym, is back, and that’s important, because at this point, there is little to no margin for error for Taylor, and every step he takes in the ring will be scrutinized.

“I think the time off not only gave him the time to heal physically, but the time to get himself together as a man,” said DiBella. “We had a long conversation a few weeks ago, and he said things to me that were very compelling. This is his life, and it’s his assumption of whatever risks a fighter faces. And he also realizes that the things that happened to him in the ring with Froch, Pavlik, and Abraham, some of it he believes he brought on to himself with not being who he was and not being true to how he was trained to be an athlete and how he was raised to be a man. He believes that he’s found himself again, is hungry again, and he knows what he did wrong and wants another opportunity to see if he has what it takes. My biggest concern for him is gonna be what it was when I first signed him. I said I want you to make some money and get out of this healthy. And that’s my same attitude about this comeback. I want him to make some money and get out of this healthy.”

In the meantime, the guy you always see at ringside either squirming in his seat, burying his head in his hands, or jumping for joy as his fighters battle it out in the ring will likely be a little more subdued. It’s not just about the thrill of victory or the agony of defeat anymore with Taylor; it’s watching to make sure the young man he rose to the top with doesn’t get hurt in the sport that has become not just a job, but their lives.

“I’m confident that he’s at no greater risk, but that being said, if he shows an inability to take a punch in his comeback, then that’s gonna raise a flag to me,” he said. “To be honest, it would raise a flag to me about any athlete that had been knocked out a few times recently. But I think he has autonomy over his own life, and he has the ability to make the decisions that dictate what risks he’s gonna take and what he’s gonna do with his own life. And based upon what I’ve seen from all the medical reports and what I’ve seen and heard from him and from Pat Burns about Jermain’s level of commitment right now and how his reflexes look in the gym and how he’s doing in sparring, there’s nothing that says to me ‘Lou, you can’t do this.’ And yeah, do I feel like I’ll take care of him better than most people would? Yeah, I do. And to some extent I think I already showed it.”

And if there is anything DiBella takes solace in as the hours tick down to his fighter’s return to the ring, it’s that he’s done his due diligence, he’s crossed his T’s and dotted his I’s, and he’s made sure that he’s given Taylor every chance to succeed tonight. Now it’s in Taylor’s hands, and DiBella is confident that those hands still have enough in them to get the job done.

“To me, a knockout’s a terrible thing to watch, but a sustained beating is far more frightening,” he said. “And the one thing I’ll say about Jermain’s career, and this is one of the things I considered in making my decision, is that I never saw Jermain take a sustained beating. I never saw him beaten from pillar to post. The Froch fight, he got caught in the 12th round. He didn’t take a sustained beating against Abraham and he was beating the s**t out of Pavlik. It was all a matter of the fear that happened in Germany, and it was a scary thing, and it was scary enough that I walked away when I did and I think it was the right thing to do then. But I think agreeing to promote now is the right thing to do now.”