The late 1990s were especially good, as the Argentine superclub won four domestic titles between '96 and '99, as well as South America's ultimate prize -- the Copa Libertadores -- in '96.
Those teams boasted huge star power, including Marcelo Salas, Juan Pablo Ángel, Julio Cruz, Juan Pablo Sorín, Santiago Solari, Pablo Aimar, Javier Saviola and MarceloGallardo, all of whom went on to greater challenges around the world.
But things have changed dramatically over the last decade. It's now been 12 years since Los Millonarios last won the Libertadores, and its loyal fans have become accustomed to failure.
River has struggled in recent editions of the Libertadores, especially last year when it was stunningly eliminated in the group stage after home and away defeats against comparatively miniscule Venezuelan club Caracas FC. On top of that, River didn't challenge in either the Apertura nor Clausura championship last year, making it nine short seasons since it last won the domestic title.
To make matters worse, crosstown archrivals Boca Juniors have stolen the South American spotlight, enjoying an almost unprecedented run of success that includes four Libertadores crowns since River last hoisted the Cup. Meanwhile, on the other end of Buenos Aires, River wasn't just failing on the field, the club had been plagued with one of the worst hooliganism problems in the world.
After River's humiliating defeat to Arsenal de Sarandí in the semifinals of the Copa Sudamericana last season, it was finally time for Daniel Passarella to step down as coach, as it seemed that it would be the only way for the Argentine organization to look ahead to the future.
If River wanted to recapture glory days of being South America's most respected club, it had to do something different -- drastic measures needed to be implemented. That was in part why Diego Simeone was appointed head coach last December.
The former Argentine international had practically zero experience as a top-flight coach -- he only retired from professional soccer two years ago. (He's perhaps best remembered for being the recipient of the retaliatory kick that saw David Beckham red-carded out of the '98 World Cup.)
But Simeone's new ideas and innovation were exactly what River was after. He worked wonders with former club Estudiantes de La Plata, guiding them to their first championship in 23 years in '06, and River expected him to do the same for them.
But Simeone's reign didn't get off to the best start. River kicked off the '08 Copa Libertadores with an embarrassing 2-0 defeat to lowly Peruvian side Universidad San Martín in Lima. Los Millonarios were completely outplayed by a club that was only founded four years ago, and after the defeat, heavy pressure mounted on "El Cholo" and his squad.
But they responded immediately. Since that horrible defeat, River hasn't lost in the Clausura and the Libertadores. With five wins, two draws and one loss in eight matches so far this season, Simeone's team looks more capable of winning a title than any River squad in recent memory.
The Copa Libertadores is River's main priority, and if it continues to bring in positive results, this could finally be its year. River was placed in Group 5, deemed by many as "the group of death." On Wednesday, it came into its difficult encounter with Chilean power Universidad Católica at the bottom of the group, and desperately needed to pick up a good result in Santiago to keep alive its chances of reaching the next round.
Los Millonarios had yet to win on the road this season, but started strongly against a team that had demonstrated its efficiency in its last group match, with a valuable victory away at San Martín. The Argentines played some exciting soccer in the first half, and went ahead just before the break when new signing Sebastián Abreu tapped the ball into an unguarded net after a superb assist from Augusto Fernández.
Right after the break, Católica hit back through Roberto Gutiérrez, and the Chilean giants piled heavy pressure as they looked to keep the three points at home. But River didn't break, and stayed in the game thanks to the heroics of AC Milan-bound goalkeeper Juan Pablo Carrizo, who made a number of fine saves.
River seemed to liven up with the introduction of tiny teenage prodigy Diego Buonanotte towards the end of the match, and snatched a vital 2-1 victory two minutes from full time with a brilliant finish from Mauro Rosales, another second-half substitute.
The victory put River atop the group and in a commanding position, as it now looks like it's in good position to advance to the knockout rounds of the competition. The team looks like it's finally beginning to pick up the kinds of results typical of a club with ambition. Its victory over Católica proved it has the necessary firepower to win in front of hostile away crowds, exactly what's expected of teams worthy of winning the Libertadores.
Look back two weeks ago and you'll find another example of River's determination this season -- its last-gasp victory over Mexico's Club América in late February was nothing short of sensational. River fed off its home crowd at the Monumental stadium to come from behind for a 2-1 win, thanks to a 92nd-minute winner from Ariel Ortega.
Much of River's new outlook falls on Simeone and his fresh ideas, but what has made the side stand out from the rest this season is the quality of the squad.
Ortega seems to have found the form that had him regarded as one of the most exciting players in the world during his four seasons in Italy and Spain. He has put on several fine performances this season, and finally seems to have taken the responsibility as the club's main playmaker.
Radamel Falcao García has also been very impressive. The Colombian international, who missed the Católica game due to suspension, is considered one of the hottest properties in South American soccer at the moment. But so is Alexis Sánchez -- the talented Chilean has been a vital ingredient for River's offense this season.
Then there's Buonanotte -- the 19-year-old may just be starting his pro career, but he has already shown enough skill and determination to become a world-class player. At only 5-foot-3, "El Enano" can easily run through defenses, and his speed has been a huge weapon.
But perhaps the player who has made the greatest impact on the River squad is Abreu. The lanky, 6-foot-4 Uruguayan international has added an extra dimension to the River attack, as just his presence has given the side more options. "El Loco" -- who is a legend in his own right in the Mexican league after scoring more than 120 goals for seven different clubs -- has notched two goals with River so far, and has also been a constant supplier to his fellow attackers.
Will this be River's year? From what we've seen so far, it surely could be. Simeone has molded a side that is more than capable of beating the very best, and as the weeks go by, River should gradually become a much stronger unit.
Los Millonarios are enjoying one of their best starts in years, and although they have sufficient depth to fight in both fronts, their clear objective is the Copa Libertadores. Anything less than the continental title would be considered a failure.