Ernie Calbert won six minor league home run titles. He also once pitched a minor league no-hitter.
Makoto Matsubara was an eleven-time all-star in Japan.
Kevin McClatchy was the CEO of the Pittsburgh Pirates from 1996-2007.
When Elmer Dessens made his major league debut in 1996, he was the first big leaguer in thirty-five years to have the first name "Elmer". There have been none since.
Gene Roof is the brother of ex-Twin Phil Roof.
Right-hander Oliver Gardner Drake appeared in nineteen games for the Twins at the end of the 2018 season. He was born in Worcester, Massachusetts, went to high school in Mount Hermon, Massachusetts, attended the Naval Academy in Annapolis, Maryland, and was drafted by Baltimore in the forty-third round in 2008. According to b-r.com, "Drake had attended a year of prep school before the Naval Academy, making him draft eligible after his sophomore year, and he wouldn't have to fulfill his military requirement if he didn't return for his junior year." He pitched very well as a reliever in rookie ball and low A in 2008. The Orioles then spent three seasons trying to make him a starter, a plan which did not work. The only success he had as a starter was a half-season in 2011, when he was a twenty-four-year-old in Class A. He missed most of 2012 due to shoulder surgery and when he returned he was back in the bullpen, where he has remained. He made in appearances in AA in 2013 and did well, but was made to repeat it in 2014. He finally was moved up to AAA in 2015 and dominated the International League, but got only two weeks in the majors before getting September call-up. He was the second midshipman to make his debut that season (Mitch Harris), but before that there had not been one since Nemo Gaines in 1921. He posted an ERA of 2.87 in 15.2 innings, but 2016 saw him back in AAA, again getting only about two weeks in the majors before a September call-up. He began 2017 with the Orioles but made just three appearances before being traded to Milwaukee for a player to be named later. b-r.com does not indicate who the player was--maybe he still hasn't been named. Anyway, Drake pitched the rest of the season for the Brewers, going 3-5, 4.44 as a Brewer. Then life got really interesting for him. He started 2018 with Milwaukee, but was sold to Cleveland on May 3. The Indians waived him, and he was claimed by the Angels on May 31. The Angels waived him, and he was claimed by Toronto on July 26. The Blue Jays waived him, and he was claimed by Minnesota on August 3. He actually pitched very well for the Twins, going 0-0, 2.21, 0.93 WHIP in 20.1 innings (19 games). The Twins waived him after the season, however, and he was claimed by Tampa Bay on November 1. Tampa Bay waived him, and he was claimed by Toronto on November 26. Toronto then sold him back to Tampa Bay on January 4. If you're keeping score at home, that's seven transfers in one calendar year. He may have thought that attending the Naval Academy would help him see the world, but I doubt he envisioned it happening this way. He stayed with the Rays for the 2019 season and had easily the best year of his career. He was still with them in 2020, but was injured much of the season and appeared in just eleven games, pitching eleven innings. His ERA doesn't look good, but one bad appearance skewed it. He was still with the Rays in 2021 but missed the entire season due to injury. He turns thirty-five today and is a free agent. If he's healthy, it seems likely that someone will sign him for 2022, but I have no idea whether he's healthy.
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