By Keith Idec

One of the biggest regrets Oscar De La Hoya has from his career in the ring is that he didn’t fight Felix Trinidad again.

Not only would De La Hoya have had an opportunity to avenge his controversial loss to Trinidad, he would’ve made another enormous sum of money for their rematch. Fans wanted a second bout between them, but Trinidad eventually moved up to middleweight and was battered by Bernard Hopkins in their September 2001 fight at Madison Square Garden.

With so much money and legacy at stake for the franchise fighter his company promotes, De La Hoya didn’t want to be left with similar regrets about Canelo Alvarez and Gennady Golovkin.

That’s a potentially costly risk they would’ve taken had they gone their separate ways last week, rather than agreeing to terms for their rematch September 15 in Las Vegas.

“There’s fights in the past – for instance, Trinidad and De La Hoya – I wish that fight would’ve taken place the second time around,” De La Hoya told Yahoo! Sports’ Kevin Iole in a video interview this week. “And people didn’t see it, and people are still talking about it. So I didn’t want that happening here. We deserve Canelo-Triple-G 2.

“The first fight was great. I believe the second fight is gonna be even better. There’s real animosity. Both guys don’t like each other. They actually hate each other and I think we’re gonna see that September 15th. So this fight is gonna be a blockbuster. There’s no doubt about it.”

De La Hoya suffered his first professional defeat to Trinidad in September 1999, but the result of their 12-round welterweight title unification fight was widely debated.

Puerto Rico’s Trinidad, who also was undefeated at the that time, beat De La Hoya by majority decision at Mandalay Bay Events Center in Las Vegas. Two judges – Jerry Roth (115-113) and Bob Logist (115-114) – scored their fight for Trinidad and one judge, Glen Hamada, had it even (114-114).

Their showdown drew approximately 1.4 million pay-per-view buys, then a record for a non-heavyweight boxing match. Money and weight were the two issues that primarily prevented an immediate rematch from taking place.

Once their promoters, Bob Arum (De La Hoya) and Don King (Trinidad), couldn’t make a deal, Trinidad moved up to 154 pounds for his following fight. He defeated David Reid, another American Olympian from Philadelphia, by unanimous decision in that 12-round fight at Caesars Palace in Las Vegas in March 2000.

De La Hoya didn’t compete at 154 pounds until June 2001, when Trinidad already was involved in King’s middleweight tournament.

Alvarez (49-1-2, 34 KOs), who’s represented by De La Hoya’s Golden Boy Promotions, battled to a controversial draw with Golovkin (38-0-1, 34 KOs) on September 16 at T-Mobile Arena in Las Vegas. The Mexican superstar’s six-month suspension for twice testing positive for clenbuterol in February caused the cancelation of a middleweight championship rematch that originally was scheduled for May 5 at T-Mobile Arena.

Keith Idec is a senior writer/columnist for BoxingScene.com. He can be reached on Twitter @Idecboxing.