The Tampa Bay Devil Rays were in a funk as the 1999 season came to a close.
Two years into their Major League existence, things had not gone well. Probably the most exciting thing about the franchise was Wade Boggs’ slow hobble to 3,000 hits. Attendance had begun to slip. The Devil Rays had finished in last place in both years, losing a total of 192 games over that span. Meanwhile, the Arizona Diamondbacks, the Devil Rays twin in expansion, had overcome the odds and reached the postseason, losing to the New York Mets in the NLDS.
Everything was breaking the right way in Arizona; the Devil Rays, in contrast, seemed cursed.
Vince Naimoli wanted to create a new spark in Tampa Bay to drive attendance back up and to also bring a World Series to St. Pete. His strategy: make big splashy moves by bringing recognizable names to the Trop.
So as the winter meetings got underway in 1999, the Devil Rays were attached to some of the bigger name trade and signing rumors in the game; among them was 29 year old outfielder Jim Edmonds.
Edmonds had made his debut in 1993 with the Angels and finished sixth in 1994 Rookie of the Year voting. A year later, Edmonds was an All-Star, and received some votes for the Most Valuable Player after launching 33 home runs and accruing 5.3 fWAR.
Edmonds would add some hardware to his trophy shelf over the next couple of seasons as he was awarded Gold Gloves in 1997 and 1998, all the while keeping up his stellar offensive production as he maintained a 127 wRC+ from 1995 through 1998, averaging 28 home runs per season.
Throughout this time, Edmonds was dealing with nagging injuries that would sideline him for weeks at a time but never for prolonged periods. However, in 1999, he finally went under the knife and missed most of the season, playing in just 55 games with diminished production.
With just one year remaining before losing him to free agency, the Los Angeles Angels made the decision to part ways with their Gold Glove outfielder and started entertaining offers throughout the offseason...enter the Tampa Bay Devil Rays.
As the Winter Meetings began in 1999, the Devil Rays and Angels were in talks about several trade pieces. There were reports of a straight swap with the Devil Rays sending former All-Star pitcher Rolando Arrojo to the Angels for outfielder Garrett Anderson. However, the most persistent rumor connecting the two sides was a proposed deal that would send Jim Edmonds to Tampa Bay for Arrojo and second baseman Miguel Cairo.
The Devil Rays became discouraged in their endeavor to acquire Edmonds after learning that he’d be unwilling to sign a contract extension with them in the event of a trade.
Had that trade been made, the offseason, and indeed Tampa Bay history, would have looked very different. A few days later the Devil Rays made a couple of massive deals as they signed Greg Vaughn to a four year deal and made a trade that sent the aforementioned Arrojo to the Colorado Rockies, along with second baseman Aaron Ledesma, in exchange for slugging third baseman, Vinny Castilla, with several other teams also getting involved in the transaction.
Later on, the Devil Rays signed outfielder Gerald Williams, effectively closing the door on a possible Jim Edmonds acquisition.
In the year that followed, Edmonds would eventually be traded to the St Louis Cardinals in exchange for All-Star pitcher Kent Bottenfield and second baseman Adam Kennedy, the Cardinals 1999 Minor League player of the Year.
Just one month after being acquired, Edmonds signed a long term contract extension with the Cardinals that would keep him with St Louis through the 2007 season. Over the course of the deal, Edmonds would enjoy enormous success as he put up career year after career year. From 2000 through 2005, Edmonds averaged 6.7 fWAR a season, garnering MVP votes in five of the six seasons, as well as six more Gold Gloves (the Rays wouldn’t have a player generate over 6.7 fWAR in a season until Evan Longoria and Ben Zobrist produced 7.2 & 8.7 fWAR respectively).
Meanwhile, Tampa Bay, Vinny Castilla came crashing down to earth hard from his Coors Field orbit as he struggled mightily at the not so friendly confines of Tropicana Field. After a season and a half, he was released only to enjoy a career renaissance back in the National League. Greg Vaughn did have some initial success with Tampa Bay, but flamed out before his four year contract was up, and he was be released in the spring of 2003.
Edmonds played until a base-running injury, sustained while running the bases following a home run, effectively ended his career. He had accrued a total of 64.5 fWAR over 17 seasons. He would appear on the Hall of Fame ballot for the first time in 2015, but fell off after appearing on just 2.6% of the ballots cast.
Would things have turned out differently had Edmonds been traded to Tampa Bay and signed the contract extension? It just adds to the long list of what-if’s in Tampa Bay Rays franchise history.