Should the Tampa Bay Rays Extend Desmond Jennings?


There is a big risk reward factor involved in extending a player like Desmond Jennings. He has a significant upside but he also could be another athlete who can’t grasp the game of baseball consistently. Jennings has made it to the majors and played as regular for the last two years. His results have been decent but not spectacular. Should the Rays extend him? Maybe or maybe not. Let’s take a look at why they should extend him.

Jennings is a superb athlete with power and speed and that is just what you are looking for in a centerfielder. He was actually offered a scholarship at Alabama to play wide receiver. He turned that down and went to junior college for a year before signing with the Rays. Turning that athleticism into a baseball player is the Rays challenge. They did it with Carl Crawford and they they have started doing the same with Desmond Jennings.

In addition, the Rays have no one on the immediate horizon who is a sure bet to take his place. Kevin Kiermaier is the current Rays minor league poster boy but no one really knows if he is Sam Fuld or a starting centerfielder. Andrew Toles looks like a top prospect after his 2013 season at Low-A, but he is a long way from major leagues and how soon he gets there remain to be seen.

Finally, Jennings may be still learning. He’s only 27 with four years and two full seasons in the majors. Ben Zobrist was in his fourth year when he had his breakout season. Jennings has all the talent to be a star, and we never know when that will fall into place.

On the other hand, the reasons for not extending him are also quite convincing. Jennings is not consistent enough to hold down a valuable spot in the batting order. He doesn’t get on-base enough to be a leadoff man and his power doesn’t come consistently enough for him to hit in the middle of the order. The Rays finally settled on hitting him sixth but they have a lot of guys who can hit sixth. They need one and two spot hitters, and Jennings has turned into that consistently.

Jennings does still have upside, but how much better can he possibly get? His two years as a regular have produced similar statistics and a slash line of .250/.330/.409. That is not going to get you on many All-Star ballots. Jennings has difficulty hitting right-handed pitching, managing an OPS under .700 against them the last two years. This is simply the player that Jennings is now.

Thirdly, you have to think that at some point not so far away, the Rays will find a centerfield option better than Jennings. Kiermaier has a chance to push him as soon as this season. A player like Toles is on the horizon. And with David DeJesus and Wil Myers both capable of playing centerfield, it could even be a corner outfield prospect who reduces Jennings’ playing time. Jennings is good, but not great, and the Rays will be able to do better than him before long.

What is the verdict on an extension? I would recommend a 4-year extension for $20 million starting in 2015 with an option for one more season and running through 2016. It would be $3.5 million, $4.5 million, $5.5 million, and $6.5 million over the four years with an $8 million option. The contract would buy out his arbitration years and his first year of free agency with the opportunity to buy out the second as well. The numbers are in line with the contracts of Ben Zobrist and Yunel Escobar. It’s the usual “a little less potential money for a little more security” game that is played when a team buys out arbitration years. The Rays will not go crazy trying to extend Jennings, but at the right price it could make sense.

Of course, after all this ink has been spilled on the subject of Jennings’s contract, it’s probably a mute point. Desmond Jennings’s agent is Scott Boras and we all know what he thinks about contracts that buy out any free agent years. He’s not for it. Boras always thinks there is some stupid team that will pay more money than a ballplayer is worth and he is usually right. So, stay tuned. This may turn out to be one of the more interesting contracts to follow for the Rays the next few years.