The distinction between five and six championships as an individual in a team sport is important only because Michael Jordan (and Scottie Pippen) have six, while other noted "major sport" stars immediately before them to the present day have either five or less (a time range that discounts Bill Russell's Celtics and the Montreal Canadiens' dynasty, among others).
Getting to six, to put it lightly, is tough, especially in today's "no dynasty" era. Maybe one half of one percent of that is because five is a more pleasing number than six (except tell that to Shaq and his four titles, because five is also a much better number than four). The rest, as they say (but with a different lead), is time and money.
Derek Jeter has five World Series championships, one more season to get six, and one of the most loaded rosters of his career (if most things go to plan) thanks to an offseason spending spree Ruthian in stature. Kobe Bryant has five NBA titles and at least two more seasons to get his sixth, but a contract (2 years, $48.5 million) many believe will become debilitating if the Lakers hope to compete for a title while he's in uniform.
So who has the better chance at getting ring number six, in the process putting themselves in a territory currently occupied only by Michael Jordan and Scottie Pippen (in terms of modern stars with 6 or more)?
The case for Derek Jeter:
If healthy, we know Derek Jeter is going to have a solid year (.290 - .310 territory), shoring up one of the Yankees' biggest holes from last season. It also should be noted he's one of the toughest players in the game when it comes to injuries. Likely, he'll suffer a minor tweak here or there, but, given his reputation and that it's his last season, he'll do everything he can to play through them if he has to. More than just himself, he also has what may be the most talented Yankees team of his 18 year career, if everything goes exactly according to plan. If most things fall into place, the 2014-15 New York Yankees will be a division-winning team/top wild card finisher with a good chance at the World Series. If only a few things work out, they'll be fighting for the wild card. That's a pretty decent margin for error. Encouragingly, almost every player returning from last year is expected to improve, a list that includes himself (by default); Mark Teixiera (also by default); Brett Gardner (gets better every year); Eduardo Nunez (tons of potential and pop, but stone hands in the field); C.C. Sabathia (coming off the worst season of his career); and Michael Pineda (by default, unless he does more harm than good). As long as free agent acquisitions Carlos Beltran, Jacoby Ellsbury, Brian McCann, and Masahiro Tanaka come close to expectations, theirs will be a dangerous/unique/fun (to watch) team.
The case for Kobe Bryant:
The Lakers have a decent future plan, but always with the potential to bomb like they did last year after picking up Steve Nash and Dwight Howard. Hopefully for Bryant, management finds a way to get something for Pao Gasol before tomorrow's deadline. Rumors have them asking Phoenix for Emeka Okafor and a first round pick; the same rumors have Phoenix willing to deal Okafor only. The Lakers are also the NBA's fifth worst team, putting them in striking distance of a crucial top three pick, or the last to go of Jabari Parker, Andrew Wiggins, and Joel Embiid. With Embiid the bigger project (and, as of now, the likely number one pick), Wiggins and Parker are capable of making an immediate impact. Even if the Lakers miss them, they'll still land someone with talent. (The experts aren't calling this one of the NBA's deepest drafts for nothing; I wonder if Anthony Bennett would have even made the first round?)
With the departure of Gasol, the Yellow and Purple will have the cap space to make a run at a free agent this summer, which Kobe will demand (which Kobe's contract demands). Add that to the current roster of mostly uninspiring role players, and it's going to likely rest on that lottery pick to make the difference between five and six.
Overall Edge: Jeter