Admittedly, when your team finishes dead last and does so mostly with mediocre veterans and an insufficient amount of young talent, it’s difficult to find the silver lining. It’s sort of like the guy standing on the deck of Titanic shouting, “What a wonderful view we have of that shiny iceberg!” That’s the kind of blind optimism that all of us find annoying–if not downright nauseating.

If there was a bright spot to be found on the awful 1990 Yankees, it was Roberto Kelly. On a team bogged down with too many Bob Gerens and Oscar Azocars, Kelly was a legitimately talented prospect. He possessed four of the requisite five tools, lacking only in arm strength, which was merely average for a center fielder. Kelly also looked like a pure bred athlete. Long and lean, but well toned from top to bottom, Kelly played the game elegantly. Scouts looking for a recipe of future stardom did not need to look any farther than the graceful Kelly.

From day one, Kelly brandished a picturesque swing from the right side of the plate. I felt that if Kelly could improve his pitch-taking ability even slightly, he could become a consistent .310 to .320 hitter who could hit 25 home runs, steal 30 bases, and draw 50 to 60 walks a season. Well, it didn’t happen. In some ways, Kelly peaked during his 1989 season, when he batted .302 with 41 walks in his first full major league campaign. After that, his patience at the plate never improved, his batting average regressed substantially, and his strikeout totals mounted. Offensively, Kelly increased only his power, as he reached a high of 20 home runs in 1991. Even in the outfield, Kelly’s progress seemed to flatline. Although he covered a substantial amount of ground with his gliding gait, he sometimes made bad breaks on batted balls and too often looped his throws into no-man’s land. Instead of getting better, Kelly simply stagnated, and in some areas, retrenched into mediocrity. For a Yankee team desperately in search of building blocks, Roberto Kelly was becoming a frustrating liability.

The arrival of Bernie Williams also complicated matters. Making his debut in 1992, the 23-year-old Williams quickly convinced the Yankees that he had advanced past Kelly as a prospect and potential major league star. Williams’ ability to switch-hit and his superior power, coupled with better defensive instincts in center field, made him the choice over Kelly. Even the throwing arm of the young Williams, which would become a concern in later years, was better than Kelly’s. So after Kelly incurred a disappointing 1992 season, in which his OPS fell to .702, the Yankees decided to explore trade options.

Most notably, the Cincinnati Reds made an intriguing bid for Kelly. They offered the Yankees Paul O’Neill (along with minor league first baseman Joe DeBerry), who had become a source of frustration for manager Lou Piniella. O’Neill’s hot-and-cold offensive game, particularly his struggles against left-handed pitching, convinced Piniella and the Reds that he would never become a star, much less a consistent everyday player.

Yankee GM Gene Michael agreed to make the deal in early November. In retrospect, the trade became a one-sided blockbuster for the Yankees, but at the time, it posed some real questions. Would it be smart for the Yankees to trade the 28-year-old Kelly for the older O’Neill, who had already turned 30? Would O’Neill ever find his way against left-handed pitching? As a Yankee fan, I certainly had mixed feelings about the trade. O’Neill’s left-handed bat at Yankee Stadium intrigued me, but so did Kelly’s all-round potential. If Kelly were to blossom in Cincinnati, the Yankees would forever rue the Election Day trade.

As we all know, Kelly did not flourish with the Reds. In fact, his career continued to backtrack. While O’Neill became a star with the Yankees, Kelly mysteriously devolved from future star to perennial journeyman, bouncing from the Reds to the Braves to the Expos to the Dodgers to the Twins over the next five seasons. For one year, he even asked reporters and fans to call him Bobby Kelly. That made him the anti-Roberto Clemente; the Hall of Fame outfielder had bristled at attempts to call him “Bob” or “Bobby” in the 1960s. After one year with an Americanized name, Kelly returned to the traditional “Roberto.” But the name changes did little to change his falling fortunes. Kelly would eventually return to New York, but not until 2000, at the tail-end of a disappointing career. Even then, Kelly lasted only ten games and missed out on playing in the World Series against the Mets.

Of all the Roberto Kelly cards that were produced during the nineties and 2000s, this Topps card–part of the 1992 set–is my favorite. Unlike most posed batting shots, which are photographed from a side or distant viewpoint, the cameraman has given us the perspective of the pitcher, only from a few feet away as opposed to 60 feet, six inches. If this photograph captured Kelly in actual batting practice, we could imagine the ball ramming its way through the camera lens. Kudos to the Topps cameraman for taking a potentially routine pose and turning it on its side to give us something different.

In some ways, Kelly’s career was the opposite of that card. He seemed to have the kind of talent that differentiated him from the rest of the 1990 Yankees, but his career ended up as nothing more than routine. He could have become a beloved part of franchise history, and an important part of a dynasty. Even today, I still feel a little bit sad about Roberto Kelly.

Bruce Markusen writes “Cooperstown Confidential” for The Hardball Times.