What if he had taken that football scholarship to the University of Alabama instead of signing with the Rays? Would the second-team All-America wide receiver from Pinson Valley (Ala.) High School have been an integral part of the Crimson Tide's national championship team this season?
If all had gone as planned, Jennings would have been a senior this season, and he would have spelled trouble for opposing defenses by flanking out on the other side of the field from star 'Bama receiver Julio Jones.
But that's a "what if" we'll never know the answer to, because Jennings is proud to point out why he changed his mind about heading to Tuscaloosa: "Tampa Bay."
"It definitely was a tough call," Jennings said. "Because at college, on top of football, you're going to school, too. Hopefully, I made the best decision. we'll see."
Jennings is an athlete the likes of which the Rays have not seen in their Minor League system since Carl Crawford came on board in 1999 after being a three-sport prep standout in Houston. Ironically, much of this year's Hot Stove talk concerning Jennings also concerns Crawford.
The left fielder is in the final year of his contract, which has helped fuel speculation that he will either be traded or turn to free agency after the season. If such a scenario does develop, Jennings could be earmarked to fill what would be a huge void. Yet the 23-year-old certainly appears to have the talent to tackle such a daunting task.
The Rays recently had four players from the organization named to MLB.com's Top 50 prospects. Of that group -- Jennings, Wade Davis, Jeremy Hellickson and Tim Beckham -- Jennings was ranked the highest, at No. 6.
The speedy outfielder had an outstanding first full year of professional baseball in 2009. In his two previous seasons, he was hurt, which prevented him from playing a full campaign. He became the MVP of the Southern League in 2009 playing for Double-A Montgomery before advancing to Triple-A Durham.
According to scouting reports, Jennings is a five-tool prospect who can play center field -- he runs very good routes. He has the ability to hit and will eventually hit for some power.
"Desmond is a wonderful athlete, that's first and foremost," farm director Mitch Lukevics said. "He's a gifted athlete that can give you a lot of good things on both halves of the inning, whether it's on defense with the right routes going after balls as a true center fielder, or offensively, having the ability to get on base and yet have the ability to drive in runs. He's a definite threat in both halves of the inning, which is really special to us."
|"I don't really want to be in the limelight. I just want to go out here and play baseball and have fun while I'm doing it."|
|-- Desmond Jennings|
Jennings will likely begin the 2010 season at Durham, but he will report to Spring Training believing he's a Major Leaguer.
"I'm going to Spring Training to compete for a job," he said. "They may think different, that I need more time, but I'm going to let them make that decision. I'm just going to go out there and play as hard as I can and push everybody, so when they do have to make a decision about me, it's a hard one to make."
Tampa Bay heads to Spring Training with Crawford in left field and B.J. Upton in center, leaving Gabe Kapler, Matt Joyce, Fernando Perez, Justin Ruggiano and Jennings fighting for playing time in right. So realistically, there is no reason for the Rays to rush Jennings to the Majors unless there is an emergency.
"Last year was his first full season," Lukevics said. "So he's still an inexperienced Minor League player. He has all the physical tools in the world. He has the mental capabilities to take the challenge on, but why rush? Let's get him some more seasoning, and if there's a real need, maybe he can knock on the door."
Jennings plans to be all ears this spring, particularly where Crawford and Upton are concerned, so he can sip from the fountain of knowledge.
"I talked to them a little bit on the field [last spring]," Jennings said. "Both are good guys. Both work hard. I just want to follow behind them, take the path they took, work like they work. It's a good opportunity."
Though Jennings is respectful, he does have the confidence seen in most great athletes. When asked if he will be intimidated around Crawford and Upton, Jennings smiled and offered, "Motivated."
Due to his standing in the organization and how he rates relative to other players close to the Major Leagues, Jennings has spent the offseason on the radar of most. But the limelight isn't something he seeks.
"I guess it feels good," he said sheepishly when asked about the attention. "I don't really want to be in the limelight. I just want to go out here and play baseball and have fun while I'm doing it."
Though all the attention has focused on the prospect of Jennings possibly replacing Crawford in left, Jennings is perfectly capable of playing all of the outfield positions. But even if the Rays re-sign Crawford, Jennings could end up in center or right field, depending on how the circumstances play out.
"It doesn't matter [where Crawford plays]," Jennings said. "I just want to be out there. I'll play anywhere -- left, right, center. I've played all three."
Jennings is so close to the Major Leagues he can see the end zone, leaving thoughts of Jones and Alabama football far behind, even though he might have been a part of a national championship team.
"I'm just happy for [Jones] and that [Alabama] finally [won] it," he said.
Bill Chastain is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.