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Going back to when major-league baseball adopted its current 30-team structure in 1998, we have 18 teams that finished last [one year, there was a tie, so I included both franchises]. The chart below shows their record for that season, for each of the five seasons which followed and, in the last column, the number of years after that last-placed finish, when the team first made the post-season. Obviously, for the most recent teams, we don't have five years worth of data, and we're still waiting for the Astros to make it back to the playoffs, so those are not present in the overall averages in the final row.
| Season | Team | Year 0 | Year 1 | Year 2 | Year 3 | Year 4 | Year 5 | Playoff year |
| 1998 | Marlins"]">Marlins | 54 | 64 | 79 | 76 | 79 | 91 | 5 |
| 1999 | Twins"]">Twins | 63 | 69 | 85 | 94 | 90 | 92 | 3 |
| 2000 | Cubs"]">Cubs | 65 | 88 | 67 | 88 | 89 | 79 | 3 |
| 2001 | Pirates"]">Pirates | 62 | 72 | 75 | 72 | 67 | 67 | 12 |
| 2002 | Rays"]">Rays | 55 | 63 | 70 | 67 | 61 | 66 | 6 |
| Tigers"]">Tigers | 55 | 43 | 72 | 71 | 95 | 88 | 4 | |
| 2003 | Tigers | 43 | 72 | 71 | 95 | 88 | 74 | 3 |
| 2004 | Diamondbacks"]">Diamondbacks | 51 | 77 | 76 | 90 | 82 | 70 | 3 |
| 2005 | Royals"]">Royals | 56 | 62 | 69 | 75 | 65 | 67 | 9 |
| 2006 | Rays | 61 | 66 | 97 | 84 | 96 | 91 | 2 |
| 2007 | Rays | 66 | 97 | 84 | 96 | 91 | 90 | 1 |
| 2008 | Nationals"]">Nationals | 59 | 59 | 69 | 80 | 98 | 86 | 4 |
| 2009 | Nationals | 59 | 69 | 80 | 98 | 86 | 96 | 3 |
| 2010 | Pirates | 57 | 72 | 79 | 84 | 88 | 3 | |
| 2011 | Astros | 56 | 55 | 51 | 70 | |||
| 2012 | Astros | 55 | 51 | 70 | ||||
| 2013 | Astros | 51 | 70 | |||||
| 2014 | Diamondbacks | 64 | ||||||
| Average | 57.3 | 67.6 | 74.6 | 82.7 | 83.9 | 81.3 | 4.4 |
The bad news
Only one side, the Tampa Bay Rays, has made it back to the playoffs less than three seasons after finishing last in the majors. They did so in 2008, after consecutive 30th-places in 2006 and 2007. If we're looking for a quick turnaround, it may well behoove Dave Stewart and his team to look closely at what the Rays did, and learn from that. Not least because that heralded a sustained run of success for Tampa, with four post-season appearances in the next six seasons. Even more impressive, they did all that without ever reaching $75 million in payroll.
But that is certainly the exception, rather than the rule. Everyone else has taken anywhere between three and a dozen years to make the playoffs again, with an average of 4.4 seasons. Indeed, the odds are against the Diamondbacks even making it back to .500, since in the first year, the average improvement was ten games, which would still leave Arizona staring up at .500, with only 74 wins. If we match the average improvement shown previously, going forward, we would get back to 81 wins in 2016, and then be at 89 wins in 2017, which should put us in or close to a playoff slot. But going by recent history, post-season action in 2015 seems like a long shot.
The good news
A couple of factors do work in the Diamondbacks favor, however. Firstly, it's now easier to get into the playoffs than ever before, with one-third of teams making it in each year. As we saw this season, with the World Series played between two wild-card teams, once you get your foot in the door, the slate is wiped clean, and a team's fate is determined entirely by how you play in October. The 88 wins posted by the champion Giants was the second lowest tally by a World Series winner since 2000, ahead of the 2006 Cardinals (whose 83 wins was enough to win the NL Central that year).
It also helps that the Diamondbacks weren't bad for a last-place team. Their 64 wins was getting on for seven wins better than the average over the period in question, and it's obviously easier to climb a mountain, if you're not starting off underwater. However, this does mean that one of the things that should help - a tendency of all teams to regress to .500 - will pull less strongly on Arizona, because they're nearer to the mark. The three worst teams on the list, the 2003 Tigers, 2004 Diamondbacks and 2013 Astros, averaged only 48 wins, but improved the following season by 29, 26 and 19 games respectively..
Conclusions
I'm sure we all hope the Diamondbacks make the playoffs in 2015. But realistically, it'd be a long shot, requiring them to do what has only been managed once in the recent history of major-league baseball. The front office may talk otherwise, but I wouldn't really expect anything else - even the public target of finishing over .500 seems like an uphill struggle, if history is any guide. I'm restraining my expectations, and would rather see the team surpass these lower goals, than suffer yet another season of lofty ambitions and severe disappointment.