Sylvester, now 40, didn't make any catches beyond high school. Being cut twice from walk-on tryouts at UCLA made certain of that. But Sylvester hasn't let that stop him.
He turned to education instead, earning a mechanical engineering degree from UCLA and a Wharton MBA from the University of Pennsylvania, before gaining real-world experience in private business. Sylvester's only foray into baseball was in the summer of 1998, after graduating from UCLA, as an intern with the Triple-A Memphis Redbirds.
But while in New York working for Sirius Satellite Radio, Sylvester could no longer ignore baseball's call. After a couple of interviews with key MLB personnel, Sylvester quit his job and made himself hunt down a baseball gig.
At the seemingly advanced age of 35, Sylvester jumped at taking an internship with the Rockies in 2005. If you compare that to Michael Jordan interrupting his legendary basketball career to try to make it as a baseball player, it doesn't. Jordan's first season was at Double-A, just two steps from the Majors. Sylvester, at an age when many folks put aside their childhood dreams for the safety of the career in hand, came in at the lowest possible level in the Rockies' baseball operations.
But Sylvester worked his way up and became a full-time employee when his internship ended -- and he continues to learn and advance. He's not making those diving catches, but as a player-development assistant for the Rockies, he's a key part of the group that builds the Minor League players who will eventually make big plays for the big club.
"It's funny -- I tell my buddies from business school and my friends that I'm getting a Ph.D. in baseball," Sylvester said. "I have an undergrad degree in mechanical engineering. I have a master's degree in finance. Now, I'm getting my Ph.D. in baseball, and I love it."
In working alongside Walker Monfort, Sylvester does a little of everything -- from statistical analysis to player evaluation to arranging travel under player-development director Marc Gustafson.
"He's well-educated, but for me, it's his work ethic," Gustafson said. "He gets so much done. He's the glue of the department. If the staff or the players can't get me, they'll go to him. He's got a leadership quality. He's not afraid to make decisions."
Sylvester's story could serve as an inspiration for all young people who have athletic-oriented dreams. For every high schooler who is drafted and actually steps onto a big league diamond -- like, say, one of Sylvester's cousins, the Braves' Jason Heyward -- there are countless Walter Sylvesters.
Yet Sylvester found another way to the Majors.
Plan A, of course, was to make it as a player. Sylvester's uncle, Kenny Washington, was a standout for some of John Wooden's renowned championship basketball teams in the 1960s at UCLA. Sylvester was going there, intent on impressing coach Gary Adams enough to earn a spot. From there, the sky was the limit.
The limit turned out to be much lower.
"I tried to walk on at UCLA twice, and I got cut twice by coach Adams," Sylvester said. "But I still loved the game."
He also loved math, so mechanical engineering was a natural major. Sylvester had no way of knowing that he was learning to think like a baseball executive, since statistical analysis as a roster-building tool had yet to receive mainstream attention.
"I love the critical thinking, the problem-solving, the analytical tools," Sylvester said. "That's what intrigued me about being an engineer."
That intrigue still paled in comparison to his love for baseball. Out of college, he worked for Pacific Bell as an outside plant manager -- "A telephone guy," he said.
On Oct. 2, 1995, Sylvester arranged to work a half-day, then knock off to watch the Angels and Mariners meet in a one-game playoff to determine the American League West title and a spot in the AL Divisional Series. The Mariners won, and baseball won Sylvester for good. He went to Wharton, this time with a plan to convince baseball that his MBA in finance was useful.
After graduating and interning with the Memphis club, Sylvester landed a job with The Disney Corporation's consumer products division in hopes of sliding into work with the then Disney-owned Angels. It's not as if this was something he hid from his bosses.
"My first day in orientation, they asked me, 'Who is your favorite Disney character?'" Sylvester recalled. "I said, 'Garret Anderson, outfielder for the Anaheim Angels.'"
Disney soon found work for him in New York with ESPN the Magazine, on the business side. Even while working for that outfit and for Sirius, Sylvester earned interviews with current MLB executives Jimmie Lee Solomon and Jonathan Mariner and current Pirates president Frank Coonelly, who was working for MLB by helping negotiate and administer collective bargaining agreements.
Sylvester felt close enough to his dream that he left Sirius and spent the end of 2004 and much of the following year pursuing work in baseball. Brian McArn, a friend and hitting coach in the Athletics' organization, helped arrange a meeting with Rockies assistant general manager Bill Geivett at the '04 Winter Meetings in Anaheim.
"He said, 'Are you sure you want to be an intern? You're 35 years old,'" Sylvester said. "I'm like, 'Sure, Bill, I'm not working.'"
When the internship ended, Sylvester's supervisor, Thad Levine, left to become assistant GM with the Rangers -- whose GM is Jon Daniels, a former Rockies intern. Sylvester landed full-time work with Jeff Bridich, who took over as director of baseball operations, and later moved to player development.
Turns out he was right about pursuing that business degree.
"At the end of the day, a baseball team decides how you want to allocate resources, like any other business," Sylvester said. "My background helps in terms of asset allocation."
If the background landed him the job, the willingness to learn is helping him advance.
Sylvester credits his parents for that. His father, Joseph, is a retired middle school principal. His mother, Roslyn, traded in a career as a biologist to become a lawyer in her mid-30s. They weren't involved in athletics, but their words have served Sylvester well.
"They're both 72 years old," Sylvester said. "My dad's favorite quote to me is, 'Son, you should call your parents. We've got 144 years of experience.' I take my dad's advice and apply it to my work world.
"If you take all the guys on my player-development staff -- from Bobby Knoop [a former Gold Glove infielder with the Angels, now a key player development adviser] to Rick Matthews [a longtime pitching coach in the Majors and Minors who is a special front-office assistant] -- I have hundreds of years of baseball experience to draw from and learn from in my role. I have an opinion, but I have so many people to talk to and share ideas with and learn from."
Said Gustafson: "He gets it."
That day as a second-grader while watching his cousin, Sylvester clearly saw that diving catches win games. While his ability wouldn't let him make such athletic plays, he never lost the desire to contribute to a winner. Now, Sylvester is exercising that with the Rockies.
"The reason I'm working for the Rockies and working in baseball is I want a World Series ring," he said. "I don't want to win a ring just once. I'm in it to win back-to-back-to-back World Series.
"When I first joined the Rockies, I felt that we wished we were good. We progressed from wishing to be good to knowing we are good, and now expecting to be good. I love being part of that."