The professional golfer died in 1999 at age 42 in a plane crash just four months after winning the U.S. Open. The crash was also one month — nearly to the day — after Stewart’s team made a record-setting comeback victory for the U.S. at the ‘99 Ryder Cup, breaking a six-year streak of defeats.
Stewart’s death left an impact on players and fans alike. For Conroy, it was a game-changing moment.
“[I thought] holy cow. This guy is on top of the world, got everything going [and] at the snap of a finger, it’s gone. If tomorrow didn’t come for me, could I say I tried and did everything that I wanted to do in my life?”
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For Conroy, his dream was to become a Major League umpire. Shortly after Stewart’s death, he enrolled in umpire school. On Tuesday, when the MLB All-Star Game comes to Marlins Park, Conroy will be the ump behind third base.
It took 18 years for him to get here — including umpiring somewhere between 1,200 and 1,500 minor league games (he lost count).
His sister, the Rev. Maribeth Conroy, the rector at St. Philip’s Episcopal Church and School in Coral Gables, remembers well her family’s love of baseball, honed watching the Boston Red Sox while growing up in a small Massachusetts town.
Indeed, much of their childhood was spent watching baseball games and eating ice cream cones. “As a family, we would go to all the [local] baseball games and A&W drive-ins for the summer,” she said. “Life was simpler back then, baseball was all you did.”
Starting at 6, he played T-ball, then moved into Little Leagues before making his high school team. He played first base, pitched and was captain in his senior year. Once he hit college, however, he began to think about umpiring — a surprise to the family.
“I think we always knew he liked sports, and he certainly played a lot of baseball growing up,” Maribeth said. “But a lot of the people we grew up with played baseball. It never occurred to us that he would want it as a career — we thought he did it for fun.”
Conroy received ample support from his parents, his sister and his older brother Steve.
“He’s our youngest son, and we’re very proud of him,” said Ed Conroy, his dad. “We were surprised but then we said, ‘Go for it.’ And he went for it and made it.’’
In our family, we like rules. I’m a priest, and he’s an umpire.
The Rev. Maribeth Conroy, rector at St. Philip’s Episcopal Church in Coral Gables
Umpires are trained at umpire school for four to five weeks (depending on the school), before being selected into the Minor League Baseball (MiLB) Advanced Course. After finishing the course, the best umpires are offered jobs in the minor leagues: Class-A, Double-A, and Triple-A. The top 15 to 20 Triple-A umpires serve as MLB call-up umpires before being promoted to the Majors.
It normally takes an umpire from seven to eight years to make it to the Majors.
For Conroy, it took 13 long years, spending roughly half a year away from home, eight- to-10-hour night drives and paltry paychecks.
“You learn to survive on minimal amounts of sleep, and you learn how to stretch a dollar,” said Conroy, now 42, married and the father of 8-year-old twin daughters. “Those things, when you put them all together in a pot, makes the journey tough. [But] it also makes it sweeter when you’re fortunate enough to make it.”
There’s also the temperamental aspect. Umpires often face the wrath of players and coaches, and Conroy has seen his share — or two.
Conroy says it comes with the job. He knows the anger is not directed at him, “but the uniform,’’ he said.
Added his sister: “[Umpires] really do stay calm. Some of it’s personality, some of it’s the rules. In our family, we like rules. I’m a priest, and he’s an umpire,” she joked.
Conroy’s career in the Minors began in 2000. He served as a call-up umpire between 2010 and 2013, before being promoted to the Majors in 2013.
He umpired the 2015 American League Wild Card Game between the Houston Astros and New York Yankees at Yankee Stadium. He worked the 2014 Japan All-Star Series, and was a replay official for the 2014 American League Division Series.
Coming a long way from his first game in the Majors — a doubleheader between the New York Mets and Milawaukee Brewers — Conroy has gotten used to the body-numbing awe he felt then. Now, he goes to work every morning feeling as if he won the lottery.
The opportunities keep him focused because “…the moment you start thinking you got this figured out, the game will humble you in a hurry.”
And watching her brother has taught Maribeth, a lifelong baseball fan, a few things about the game.
“I guess I’m more protective of umpires now,” she said. “But, I would never question my brother on an umpire call.”