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There is a very large overlap in people that play both baseball and football. While that overlap mostly happens at a high school and college level, a few have managed to crack the pros in both sports. It’s obviously quite hard to do, but for whatever reason, that combination of sports appears more than any other combination of major sports in the US.
Over the years, the Yankees have had several people in the organization who either have played both sports, or at some point considered it. These five are probably the most notable.
George Halas
Halas is known as the legendary player, coach, executive, and owner of the Chicago Bears, who helped former the league now known as the NFL. Before winning any of his six championships with the Bears, he was a mediocre outfielder for the Yankees.
After serving in the military and graduating college, Halas signed with the Yankees and pretty much jumped straight to the majors. He proceeded to go 2-for-22 at the plate in 12 games, got injured, and never played baseball again. Given his status as a football Hall of Famer, everything turned out okay for Halas.
Hinkey Haines
I did a full article on Haines, which you can find here. He is probably the least known person on this list, but he does have an accolade no one else does. He is only person to have won both an MLB and an NFL championship.
As the Murderer’s Row 1927 Yankees were wrapping up their World Series championship, Haines was in the midst of leading the Giants to that season’s NFL title. Four years earlier, he was still a semi-pro football player and a member of the Yankees’ first ever championship team in 1923.
Haines wasn’t exactly a great baseball player, as he recorded just four major league hits. He did score the game-tying run in the Yankees’ championship-clinching win, though. That would be his final major league baseball game, but his contributions on that day allowed him to be the sole member of an extremely impressive club.
John Elway
In 42 games in low-A, Elway hit .318/.432/.464. Obviously that’s a long way to go to the majors, but that’s pretty good. Elway could have been something as a baseball player. Instead, he’s more known for using the Yankees as leverage than playing for them.
The future football Hall of Famer was a two-sport star at Stanford when the Yankees took him in the second round of the 1981 draft. He then played in the minors in 1982 for the Oneonta Yankees. Despite his success on the baseball field, he returned to Stanford to play in the ‘82 college football season.
Back on the football field, he became an All-American quarterback and found himself selected first overall in the 1983 NFL draft. Elway had no interest in playing for the team that selected him with that pick, the Baltimore Colts, so he and his agent publicly began to float the idea of him giving up football and playing solely for the Yankees.
Eventually, their power play worked, and Elway was traded to the Broncos, for whom he went on to have an extremely successful career. He never played baseball again after 1982. Meanwhile back in that 1981 MLB draft, the Padres selected Tony Gwynn six picks after the Yankees took Elway. Oops.
Bo Jackson
Like Elway, the Yankees selected Jackson before they hit it truly big on the football field. Unlike Elway, Jackson never played a game in the organization.
The Yankees took the then high schooler in the second round of the 1982 MLB Draft and reportedly offered him a $250,000 signing bonus. He turned them down and accepted a scholarship offer to Auburn, as his mother wanted him to do. Presumably, it was also so he could play college football.
Jackson went on to win the Heisman Trophy and go #1 in the NFL Draft. Like Elway, he did not end up playing for the team that drafted him, but his story is far more complex.
Jackson went on to be drafted out of Auburn by the Royals in the 1986 MLB Draft, and ended up playing in the majors later that year. His baseball career peaked in 1989 when he made his first and only All-Star game. Injuries ended up cutting his careers in both sports short.
There are plenty of people with more accomplished baseball and football careers. However, there is a reason Bo Jackson is an icon. Had he actually signed with the Yankees out of high school, he might not have gotten the chance.
Deion Sanders
While Haines has won a championship in both sports, Sanders is the only person to appear in both a Super Bowl and a World Series. (The Super Bowl was still decades away from existing when Haines was playing football.) Before any championship game/series appearances, he made the major leagues with the Yankees in 1989.
The Yankees selected him in the 30th round of the 1988 MLB Draft. The next year, he was taken by the Atlanta Falcons in the NFL Draft. Like Elway, Sanders used the Yankees as leverage against his new NFL team, but Sanders actually ended up suiting up in pinstripes.
He made his major league debut on May 31, 1989. He played just 71 games across two seasons for the Yankees. He wasn’t great for the Yankees, with the highlight of his time in New York being a inside the park home run in 1990. They released him in September.
The Braves picked Sanders up in January, and he went on to give them a couple solid seasons. It was in Atlanta where he appeared in the World Series, and also played in a football game and sat on the bench for a playoff baseball game on the same day.
As for his NFL career, he won two Super Bowls, made eight Pro Bowls, and made the Hall of Fame. Pretty good.
Sources
https://sabr.org/bioproj/person/586380d8
https://www.milb.com/milb/news/before-the-broncos-elway-eyed-the-bronx/c-112011776
https://www.nytimes.com/1989/08/29/sports/sports-people-football-deion-sanders-fed-up.html