It's hard to believe that the Rays were at one time not The Little Franchise that could, but you have to go alllllll the way back to the year 2005 to find when they were still flailing away. At that time in 2005, they were in the midst of the final death throes of the GM Chuck LaMar/Owner Vince Namoli era.
It was June 2005 and the annual draft was upon the "Devil" Rays. The Rays were in their customary spot of picking in the Top 10 of the draft, this time in the 8th slot. There was a great amount of internal debate within the Devil Rays' front office on who to take with their first round pick. There was a faction in the front office that wanted to take Florida high school star Andrew McCutchen, but there was a larger more vocal faction that wanted to get a college player to help the team much sooner (read: try and save their jobs). If anything of these first two paragraphs sound hauntingly familiar to you, just flash forward two years to the summer of 2007 when the Pirates went "safe" and picked Danny Moskos in the draft. It's no coincidence that LaMar and Littlefield were both considered two of the worst GM's in modern years.
I thought it might be interesting to contemplate how Andrew McCutchen's career may have been different had that minority faction in the Devil Rays' front office won out.
Let's assume that McCutchen signs with the Devil Rays and at the slot amount, just as he did with the Pirates. He would probably have been assigned to Princeton of the Applachian League, as the Devil Rays don't have a Gulf/Arizona League team for HS players. The Rays are notorious for going slow with their young pitchers, but not as much with their hitters, so in 2006 let's say that McCutchen would have been assigned to the Southwest Michigan Whitecaps in the Low A Midwest League. The Midwest League is a much tougher hitting environment, especially in the early part of the year due to cold conditions, but it is safe to assume that McCutchen would still have done well.
In 2007, McCutchen would have been promoted to Vero Beach in the Florida State League. The FSL is considered to be a pitcher's league, due to the oppressive heat and humidity in the summer, plus some expansive outfields at certain parks. The Pirates aggressively promoted McCutchen to Double A Altoona Curve in 2007, but the Devil Rays would probably have taken it one rung at a time with him.
2008 would have seen McCutchen promoted to the Montgomery Biscuits in the Southern League, which skews towards a hitters league. It is easy to envision the 21 year old McCutchen doing quite well in this league. Continuing with the one level at a time theory, McCutchen would have gone to the Durham Bulls in 2009 as a 22 year old in the International League. The Devil Rays are very cost conscious and like to control their assets more than any team in the league, so it is not hard to imagine McCutchen spending all of 2009 in the IL.
What would have happened in 2010, though? At the major league level, BJ Upton was firmly entrenched in CF for the now-Rays. Carl Crawford was ensconced in LF, but would soon be leaving the Rays for free agency at the end of the year. Ben Zobrist was coming off of a huge breakout year in 2009, even though his 2010 was a down year, but he wasn't going anywhere in RF.
If the Rays were out of playoff contention, it would be conceivable that they could have traded Crawford mid-season to recoup some value in prospects. However, the Rays made a playoff push in 2010. As a result of the playoff run, plus the presence of three solid options, it seems as if McCutchen could have spent a 2nd full season in AAA.
McCutchen may not have made his major league debut until the start of the 2011 season (as a 24 year old), replacing Crawford in LF, as Upton is considered to be a high quality CF. This past season may have been McCutchen's rookie season if he were a member of the Rays, not his 3rd overall season and 2nd full season like it was with the Pirates.
As we have seen with Evan Longoria, Wade Davis, and recently Matt Moore, the Rays are not shy about locking up young talent early on in the process. The Pirates are trying to do that right now, but McCutchen may have concerns about the future of the Pirates. That may not be the case with the Rays, as they have been quite successful in recent years.
As difficult as it would be to imagine McCutchen in any other uniform, it is possible that he would have had a slower yet ultimately more rewarding career, in terms of both team success and short-term financial success, if the "Devil" Rays had made a different decision in that draft room in 2005.
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