Here's a list of World Series winners over the last fifteen years with playoff appearances and regular season wins also included. If ATL wins this year they would join the list at 1 WS | 7 PO | 1,208 W (8th), if HOU wins they would join BOS & SFG as the only teams on the list with multiple World Series wins... BOS: 3 WS | 8 PO | 1,274 W (4th) SFG: 3 WS | 5 PO | 1,188 W (10th) LAD: 1 WS | 11 PO | 1,332 W (1st) NYY: 1 WS | 11 PO | 1,329 W (2nd) STL: 1 WS | 9 PO | 1,274 W (3rd) CHC: 1 WS | 7 PO | 1,187 W (12th) HOU: 1 WS | 6 PO | 1,146 W (17th) PHI: 1 WS | 5 PO | 1,171 W (14th) WAS: 1 WS | 5 PO | 1,161 W (15th) KCR: 1 WS | 2 PO | 1,067 W (28th) Looking at the list the most obvious takeaway to me is that winning the World Series is INCREDIBLY HARD, mostly because the postseason is susceptible to large degrees of randomness. If it weren't, the Dodgers & Yankees who have spent however many billions on payroll, and the Cardinals who have some sort of Devil Magick, would have more than one World Series each to go along with their 31 combined playoff appearances as the winningest teams of the last 15 years. But even looking at a list of World Series winners, I still see a lot of heart break. The Royals with 13 years of irrelevance around their blip, the Nationals whole thing falling apart almost immediately after winning it all, the Phillies spending however many billions to not even make the playoffs anymore, the Astros success tainted by banging on a garbage can, the Cubs "dynasty" crumbled largely at the hands of the Brewers, all the sad STL/NYY/LAD fans in those 28 postseasons that didn't end in a World Series win, so what was really gained? If the game was indeed designed to break your heart like Giamatti said, you better learn to love heart break.