Thairo Estrada was signed by the Yankees an international free agent on August 2, 2012, for $49,000. Estrada was not as highly touted as other players the Yankees signed in the same free agent class, like catcher Luis Torrens.
Since he signed so late in the year, Estrada did not make his professional debut until the following season. At 17-years old he was one of the youngest players in the Gulf Coast League, being over 2 1/2 years younger than the average player in the league.
That season appeared in 50 games for the Gulf Coast League Yankees, hitting .278/.350/.432 over 199 at bats. Out of the 49 hits he had that season, 11 were doubles, 5 were triples, and 2 were home runs.
On July 6, 2013, Estrada had his best game of the season going 3-for-4 with two runs scored against the Gulf Coast League Phillies. That season he also hit .323 during away games and crushed left-handed pitchers hitting .400/.481/.556 in 45 at-bats.
At the start of 2014, Estrada went to Extended Spring Training to prepare to join a short season team in June. When June came, he was assigned to the Staten Island Yankees where manager Mario Garza called him a very exciting player to watch. “He is small in stature,” Garza said, “but he plays the game the right way, plays hard. He is an on-base machine, dominates the routine play.”
Estrada went on to appear in 17 games for the Staten Island Yankees. In 59 at-bats, he hit .271/.348/.288 and stole seven bases. His season was cut short when he suffered a leg injury on July 4, 2014, in a game against the Hudson Valley Renegades. He suffered the injury while running from first to home on the double.
After being shut down for most the season, he was sent down to the Yankees Complex in Tampa to rehab. He closed out the season appearing in six games for the Gulf Coast League Yankees at the end of the season. He hit .273/.304/.364 on his return.
The 2015 season saw Estrada return to the Staten Island Yankees where he hit .267/.338/.360 in 63 games, 247 at-bats. His success earned him mid-season New York-Penn League All-Star honors after hitting .306 before the All-Star Break. He had 73 at-bats against left-handed pitchers, hitting .356/.429/.466 against southpaws that season. The majority of his time saw him hitting third in the order, batting .296/.370/.407 in the three-hole.
Most of Estrada’s time in the field in 2015 came at second base, playing 45 games there as opposed to 19 games at shortstop. It was the first time he played second base since the 2013 season when he played nine games at the position for the Gulf Coast League Yankees.
Thairo Estrada started the 2016 season with the Charleston RiverDogs of the South Atlantic League. The young infielder found himself in a prospect-laden infield that included his 2015 teammate Kyle Holder, 2014 International Free Agent Hoy Jun Park, and Angel Aguilar. He appeared in just 35 games for the RiverDogs, hitting .286/.324/.429 in that span before earning a promotion. He continued to hit well on the road with a .333 average, .350 OBP and .551 slugging on the road versus a .226 average, 294 OBP, and .274 slugging at Joseph P. Riley Park. He also hit right-handed pitchers better than lefties with a line of .301/.339/.447 against righties vs. .243/.282/.378 against southpaws.
On May 23, 2016, Estrada earned a promotion to the Tampa Yankees. In 83 games, he hit .292/.355/.375 in the Florida State League. On September 4, 2016, he had his best game in his career thus far going 4-for-4 with three doubles and one RBI. With the T-Yanks, he hit .317/.412/.378 against lefties and ended the season strong with a .306/.370/.379 line after the all-star break. In total, he had 28 multi-hit games between both levels.
Estrada moved around the infield in 2016, spending time at second base, third base, and shortstop. Most of his games came at second where he had a .961 fielding percentage in 57 games, followed by third base where he had a .958 fielding percentage in 47 games. Esaw the least amount of time at shortstop where he appeared in just eight games in 2016. He committed only 16 errors in 376 chances which were good for a .957 fielding percentage in total.
Estrada spent the entire 2017 season with the Double-A Trenton Thunder of the Eastern League and had his best season. In 122 games he hit .301/.353/.392 with 19 doubles, four triples, and six home runs while driving in 48 runs in the regular season.
In the Eastern League playoffs, Estrada impressed, even more, hitting .407/.484/.630 in seven postseason games. Including hitting for the cycle against the Binghamton Rumble Ponies on September 7. That game he drove in three runs.
With the Thunder Estrada earned his second nod to a mid-season All-Star Team and was also named a post-season all-star before reporting to the Arizona Fall League where he shined for the Scottsdale Scorpions. In the AFL he was named to the Rising Stars Game. With the Scorpions, he hit .342/.381/.430 in 20 games.