The answer to this question depends on how you define success.

If success if defined in terms of money, then De La Hoya had a better carrer. Although, Tito did very good money, only a few boxers like Tyson or Holyfield can compete (boxing earnings).

But in the other hand, De La Hoya really tried to influence the Mexican fans and tried to become a national hero. Trying to achieve this goal he beat an old, worn out Chavez, which I believe hurt more. If you measure Tito's success in this area there is NO WAY De La Hoya will be close to Tito. Tito really became a national hero, he paralized and made a whole country to merge forgetting any type of differences. Every Tito's fight was a national event, full of emotions (recognizing his clear losses). Cotto is on his way, but definitely not at this level yet on the island.

De La Hoya has his trade mark of "Golden Boy", but I am sure he and any other boxer can be jelous of this type of Tito's success that very few people had achieved.