In 2005, when the International Olympic Committee voted to drop baseball and softball from the 2012 games, it looked like a permanent strikeout for an—really the—American pastime. It had never come close to earning the same following on the biggest global sports stage, despite its popularity in Cuba, Japan, China, and Venezuela, among others.

But baseball and softball may actually be on deck for the Olympic lineup in 2020 Tokyo games. While it’s about as difficult to reform the IOC as you’d expect from a massive, international bureaucratic organization, the wheels are starting to turn.

An official ruling will not be made until 2016. But, if baseball and softball find their way to Tokyo, it will be thanks to one of the weirdest pitcher/catcher combos in history—royalty (or kind of) of two former global enemies, coming together.

Antonio Castro, the son of Cuba’s former dictator (you know, Fidel) will serve as the “global ambassador” of the newly formed World Baseball Softball Committee (WBSC). Ed Colbert, brother of beloved U.S. comedian Stephen Colbert, will lead the legal proceeding as general counsel.

This seemingly odd couple between the son of Cuban political royalty and the brother of an American entertainment legend is so far working beautifully.

“He’s a nice guy!” Colbert immediately said of Castro, although he stressed they don’t exactly work together. “We don’t go out on the field at the same time. He’s like the pitcher, and I’m the first base coach,” he said with a laugh.

After last month's Cuban embargo lift, the MLB quickly and subtly altered its relationship with Cuban players to build a better relationship abroad. Yesterday, prospect Yoan Moncado was the first to take advantage of it. He signed a sworn affadavit saying, among other things, he wouldn't return to Cuba. With it, he became a free agent.

The IOC plan, however, wasn’t just a matter of geographical neighbors Cuba and the U.S. coming together. They needed the athletic ones—baseball and softball—to unite, as well. Baseball and softball have traditionally operated as two separate sports federations, despite their similarities. But after they both got the boot from the IOC a decade ago, they realized their best shot in was working together.

“The signals from the IOC were that in order to get back on the program, they should merge into a single organization,” explained Colbert. “So if they put baseball and softball back in, it would be treated as a single sport.”

Under IOC rules, the summer Olympics doesn’t have more than 25 sports, generally. (That’s not written in stone because, well, it’s the IOC). If there were to be room for only one sport, baseball and softball would effectively compete against each other—plus squash, karate, and other sports—to get back in. But by joining together as a single sport, they’d have broader appeal and wouldn’t knock each other out in a battle for a final slot. In February 2014, they consummated their union in the establishment of the WBSC.

To an IOC outsider, this maneuver may seem like a loophole of sorts, but it is actually pretty standard. Colbert, who has provided legal counseling to various sports federations for nearly 40 years, explained that swimming is considered a single sport for Olympic purposes, despite the fact that is has multiple disciplines—so that means diving, synchronized swimming, water polo, that all fall under it.

Uniting baseball and softball under a single federation is just one step in the long haul to Japan in 2020. The WBSC is benefitting from very recently approved flexibility in IOC rules in changing the sports program. Under the old rules, the lineup of sports had to be slated at least seven years prior to the Olympics, but in December of 2014, the IOC voted to “lighten up” some of the restrictions, said Colbert, including which sports will be included in the next Olympics.

That’s not the only factor that’s in the WBSC’s favor. There’s also the host country, Japan. Baseball and softball are arguably as big in that country as they are in the U.S.—perhaps even more so. Babe Ruth toured the country to mass acclaim in the 1930s. Japan is the reigning Olympic softball champion. Since the 2020 host country has to pay for the stadium and accommodations for the sports in the lineup, the IOC is “very sensitive” to their national desires, said Colbert.

The odds for baseball and softball returning would not likely be as strong “if the Olympic games went to, say, Istanbul,” he said. “That country doesn’t have a great history of playing the sport.”

Still, even though the WBSC has been working to convince Japan to essentially amend the initial bid it submitted to the IOC to include the sport, the host country then needs to successfully convince the IOC. Getting the committee’s 115 members to approve a change could likely be a massive effort. Colbert compared it to “a fleet of ships that have to be coordinated when they turn. There are a myriad of interests.”

With the rather gigantic task of convincing both the host country of Japan and the IOC to let the sport return, does Colbert really think baseball and softball could once again be part of the Olympic lineup?

“In my personal opinion as an attorney, I think the stars are aligned for this to happen, especially since Japan is supportive of adding sports—and particularly baseball softball,” he says. “There’s already been a presentation made for the IOC which was made in Tokyo in early 2014, and then discussions later in 2014. [The WBSC] needs to convince them they’ve got multi-national appeal. I think we’ve done all of that.”

Disclosure: Ed Colbert works for Kenyon & Kenyon, which does litigation for IAC, The Daily Beast’s parent company.