Yep. Cuba had a lot of ideological incentives to keep playing the U.S. in sports. Not only did they have a pretty decent development program of their own, but they also had access to the Soviet athletic training and development system during the Cold War. This allowed Cuba to be a serious opponent, if not dominant outright, in several sports but most notably boxing, track and field, baseball, wrestling, judo, and weight-lifting. These strengths were generally more notable at regional competitions like the Pan-American Games, but Cuba consistently medaled in the Olympics as well.

Cuba probably reached its high-water mark in 1991-1992 with the Pan-American Games hosted in Havana and the 1992 Olympics hosted in Barcelona, but since then, its athletic fortunes have been on the decline. It still does very well relative to the size of its population and economy, but as with other former Soviet client states, the end of the U.S.S.R. and its state-supported development system has hit its own athletic programs hard. While the facilities and training programs still largely exist (mostly, though not entirely, in Russia), their services are not offered for free, and Cuba's had issues acquiring the hard currency it needs to pay for athletes' rooms, board, and training. The prospect of closer ties with the U.S. raises the possibility of Cuban athletes' traveling, not to Russia, but to the U.S. for advanced training in the future.

Side note: The 1984 Olympics was not the only one that Cuba missed during the Cold War. It was also among the few nations to boycott the 1988 Seoul Olympics in solidarity with North Korea. The North Korean government was pretty angry that no serious effort had been made for North and South Korea to jointly host the Games. In fairness, the IOC did examine the possibility, but came to the conclusion that the North Koreans were in no shape to host anything larger than a three-legged race.

Anyway, NK called for a boycott by fellow Soviet/Chinese client states, but few nations paid attention. South Korea's fortunes had been on the rise for some time by that point (SK's economy surpassed NK's as of 1975) and South Korea went on a charm offensive with China and the Soviet Union to drum up support, not only for their Olympics but also for trade deals and diplomatic recognition. They succeeded, which was a terrible shock for the North Koreans. This was arguably the start of NK's true isolation in world politics, or at least when they realized that ideological kinship with the Soviets and the Chinese wasn't enough to prevent the latter from pursuing closer ties with their rivals to the south. Put more simply, the world had changed, but they had not changed with it. The Kims sort of floundered for a bit, and then:

• Bombed Korean Air flight 858 in an effort to create a security crisis for the Olympics
• Bid for the 1989 World Festival of Youth and Students as a kind of major-event consolation prize, and:
• Wasted enormous sums of money building athletic facilities, hotels, and what remains the biggest stadium in the world in an effort to prove that they could have co-hosted the Olympics, or at any rate a big international event.

So some of the stuff we still see knocking around today is owed to this little slice of history. The insane security surrounding the Olympics is partly the result of Korean Air 858, and Rungrado -- that massive stadium -- now hosts NK's famed "mass games," which is a big tourism draw and one of their few dependable sources of hard currency. Unfortunately, NK's building and spending mania in this period also contributed significant stress to an already-wobbly system, and did so at the worst possible time.

Getting back to Cuba ...

Since the end of the Cold War, competitions held within the U.S. have become increasingly tense for traveling Cuban teams. The "Wet foot, dry foot" policy in the U.S., which was the result of the 1995 amendment to the 1966 Cuban Adjustment Act, has been a real problem. Cuban players are entitled to remain in the U.S. the moment their plane touches down, and that little quirk of immigration law has occasionally played havoc with their line-ups. Cuban team leaders have policed their teams heavily over the last two decades, to the point of not allowing them outside hotels without an escort, but players still get the drop on them. As recently as this past summer, Cuba lost four of its players to defections during the CONCACAF Gold Cup (and then got trounced 6-0 by the U.S.), and then lost another 4-6 players during Olympic qualifiers.

Closer U.S.-Cuban relations has actually accelerated this tendency, because the U.S. is likely to drop "Wet foot, dry foot" and Cubans will lose privileged immigration status. Consequently, a number of them see a window of opportunity that may be rapidly closing.