A self-proclaimed "old country boy" from the town of Orangeburg, South Carolina, he was drafted ninth overall by the New York Mets. Four years later, Winningham found himself in Cincinnati, although it almost never happened.
Following his debut with the Mets in September 1984, Winningham was traded to the Montreal Expos while playing winter ball in Venezuela (he actually found out when the trade appeared on the ticker at the bottom of the TV while he was watching Monday Night Football). After playing in Montreal from 1985 into the 1988 season, Winningham was informed he would be sent to Triple-A.
"I just decided, `You know what, I'm not going. I'm going to retire,'" he said. "I said to (Expos general manager) Mr. Dombrowski, `Sir, this isn't the only job I know how to do. If you have any respect for me, you'll draft trade me. But if not, thank you for the opportunity.' We were in Atlanta for a game, I left, and by the time the game started, I was home."
This was leading into the 1988 All-Star break, and right as games resumed, he got a call from his agent saying he was going to be a Red. Coincidentally, the Reds were starting the second half of the season in Montreal, so his stuff was simply moved from the home clubhouse to the visitors.
Winningham spent the remainder of the '88 season with the Reds as well as the next three seasons to follow. 1989 was a down year for the Reds, but heading into 1990, he knew the team had something. There was plenty of talent and with the addition of Lou Piniella, the team had a clear structure.
"He gave you your roles right up front," Winningham explained. "Plain and simple. He'd say `You guys are playing every day, you guys are the five starters, you'll come off the bench,' and that was that."
A bench player in the majors is possibly the most difficult job in the sport. You can go multiple days without seeing the field or you could be call in at a moment's notice, and sometimes in the most crucial situations.
"I got comfortable doing it from listening to Ken Griffey Sr., Ron Oester, Joel Youngblood. Guys that were starters at one time and become role players, pinch-hitters and stuff like that. Those were the guys I listened to."
But it takes more than just listening to be a productive role player and keep that job.
"I had to work twice as hard as everybody that started," he said. "Because they knew they were going to play every day and get four at-bats. I didn't know when I was going to start so I had to take that extra batting practice, early hitting and stuff like that. I had to prepare myself for what circumstances would come up.
"You don't sit there for eight innings. You stay one step ahead of your manager, and one step ahead of their manager. When our pitcher is struggling and coming to hit, and they got a lefty, every right-handed batter has to get ready. If there is more than one, all of us get ready. We go down in the tunnel, get ourselves mentally prepared however that is, everybody has their own routine. Then we come back and see if we get in and do the best we can."
The most notable instance for this came in Game 4 of the 1990 World Series. The Reds were up 3-0 on the heavily favored Oakland Athletics and looking to complete the unfathomable sweep.
"Glenn Braggs and I - Lou already told us these are our horses and we're going to ride them til we die, so we really weren't going to play - we had our pom-poms on and our seats propped up and we were ready for every game to cheer the guys on."
But Eric Davis and Billy Hatcher both sustained injuries early in Game 4, and the momentum was on the verge of swinging to Oakland. Hatcher was hitting .519 in the postseason with a record .750 average and seven consecutive hits during the Fall Classic. With big shoes to fill, Winningham was ready and delivered a 2-for-4 performance and scored the winning run.
"We didn't know who Lou was going to put in the game so we ended up getting loose together," he said. "And then Hatch went back out and I sat down. And when Eric got hurt, Glenn went in for Eric. And then Hatch couldn't hit, and that's when I went in for Hatch. It was just meant to be I think.
"I was just blessed to even get to the World Series, let alone win it. And to go out and bunt with two strikes, get two hits, score the winning run…man you're like…wow. But it happens so fast because this is what you do, this is your job, this is how you do it. Now the older I get, the more you really appreciate the accomplishments we all did, and especially your own, whatever that is. I look back like golly, I did that?"
Since being a super sub in the Reds World Series-clinching 2-1 win over the Athletics, Winningham played a couple more years before calling it quits following the 1992 season with the Red Sox. He has kept busy since then, coaching in the minor leagues after retiring until heading home to spend more time with his son. At that time, he began working at UPS and started a program at a baseball program at Claflin University in Orangeburg, a college that was without baseball for about 50 years.
A few years later he retired from UPS and eventually joined the Tampa Bay staff as an outfield and baserunning coach in A-ball. He did that for two years then went to Milwaukee for two seasons before leaving the Major League scene. Currently, he is a high school baseball coach in his hometown but still makes the occasional trip to Cincinnati for card shows and Reds events. When in town, he makes sure to catch a Reds game and of course find time for his favorite Queen City staple, Montgomery Inn. He also is a regular coach at Reds Fantasy Camp in Goodyear, Ariz. each spring.