When signing a talent from a foreign league, you don’t necessarily know what to expect. You can do all the in-person scouting and do all the statistical breakdowns you want, sometimes the jump in talent from another country to the majors ends up being too much to overcome. In cases like Hideki Matsui, he was an other-worldly hitter in NPB and ended translating that to a very good MLB career. However in cases like Kei Igawa, a successful overseas career didn’t mean anything, and he was crushed at the major league level.

In the case of Orlando “El Duque” Hernández, there were a lot of unknowns. Sure, you could get some info and stats from the Cuban league and he had pitched against some major league talent in appearances for the Cuban national team, but due to international relations, it wasn’t always a simple task to get info and scouting out of Cuba. Beyond that, circumstances beyond Hernández’s control got him banned from baseball by the authorities in the years leading up to his defection.

Due to all that, there was some amount of wishful thinking involved when the Yankees inked El Duque to a deal in 1998. However, everything ended up working out pretty swimmingly.

Orlando Hernández
Signing Date: March 23, 1998
Contract: Four years, $6.6 million

Born to a father who had played in the Cuban National Series, with two brothers — including future fellow big leaguer Liván — Orlando made a name for himself on the baseball fields of Cuba. As a youngster, he wasn’t expected to be much of a ballplayer, as he was told as an 11-year old that he had no ability. However, he had a great love for the sport, and continued to work at it.

While it took a little while, Hernández broke into the Cuban league with the Industriales, who are the most successful team in Cuban National Series history. Eventually, he became one of the league’s most decorated players, setting the all-time pitching wins record. He also became a regular on the Cuban national team, helping them win gold at the 1992 Olympics in Barcelona.

As that was happening, his brother Liván also began to make a name for himself. Liván became a bit more disenchanted with life in Cuba a bit earlier than his brother and defected in 1995, eventually signing with the Florida Marlins. Between that, his high profile, and a misunderstanding of Orlando’s relationship with a sports agent, that put him under a big spotlight under the authorities. Worried that he would follow Liván in defecting, Orlando was kept off the Cuban roster for the 1996 Olympic baseball tournament in Atlanta, and he was eventually banned from playing in the National Series. Whatever level of disenchantment Orlando had previously, that certainly ramped it up massively.

Banned from playing the sport he loved, Orlando decided to defect himself over Christmas 1997. The boat he was traveling on was intercepted by the US Coast Guard and Orlando and the other travelers were sent to a detention center in the Bahamas. After some intervention and lobbying from El Duque’s future agent Joe Cubas, the US eventually allowed the travelers to seek asylum in Costa Rica, which eventually led to them being able to obtain US visas. With the help of the Yankees, El Duque obtained one, and eventually signed with the team for four years and $6.6 million in March 1998.

(For more information on his upbringing and defection, I went into more detail in our post on Hernández as part of our Top 100 Yankees series from a couple years ago.)

Having not pitched in an organized game in a little while, Hernández went to the minor leagues to start his career in America. After a couple months there, and an injury in the rotation caused by David Cone’s mom’s dog, El Duque got called up to the big leagues in June. In his debut, he struck out seven Devil Rays, and followed that with a complete game victory over the Expos in his second game. From there, El Duque and his big league career were off to the races.

With his distinctive high leg kick and ability to squeeze an eephus in there, Hernández quickly became an invaluable and electrifying part of the Yankees’ rotation. He cemented his place there with a rookie season where he posted a 3.13 ERA (142 ERA+) in 141 innings, finishing fourth in AL Rookie of the Year voting. He followed that up by allowing just one run in 14 combined innings over the Yankees’ playoff run, as they completed their historic 1998 season with a World Series title. That includes seven shutout innings in ALCS Game 4, with the Yankees facing the only real adversity they ran into in those playoffs, as they trailed the series to Cleveland 2-1.

El Duque followed that with another good season in 1999, and that time around, his heroics won him the ALCS MVP for his excellent two starts against the Red Sox. The Yankees completed a three-peat in 2000, by which point, Hernández had forever become a beloved Yankee. He even had his own dance, as immortalized in a commercial featuring Cone and Luis Sojo.

His 2001 and ‘02 seasons were a bit injury-plagued, leading to the Yankees trading him in January 2003. He came back as a free agent in 2004, before playing for a couple different teams over the final years of his career. El Duque did win one last World Series ring for the road, helping the White Sox take home the crown in 2005.

For as much as he was a legend in Cuba before ever taking a major league mound, Orlando Hernández’s signing still represented some amount of risk. In this case, it was a risk worth taking.

See more of the “50 Most Notable Yankees Free Agent Signings in 50 Years” series here.