1. 2008 - Pirates select Buster Posey in the June draft.
In 2008, the Pirates had the second overall pick in the June draft. They selected Vanderbilt third baseman Pedro Alvarez, considered one of the elite talents of the draft. It was not a bad selection by any means at the time, and Pedro Alvarez worked on justifying it this past season, putting up 2.9 WAR while smacking 30 homeruns for the Pirates. That allowed Florida State catcher Buster Posey to fall to the San Francisco Giants who selected him fifth overall.
Posey broke into the majors as a rookie in 2010 and promptly posted a 4.2 fWAR season. An injury cut his season drastically short in 2011, but he bounced back last year to post 8.0 fWAR season and win the National League Most Valuable Player award. He's also been a member of two world series teams for the Giants in the last three years. Imagine if the Pirates had selected Posey instead of Pedro Alvarez, who may have not been run over by John Buck in 2011 and would have played three full, healthy years by now. In addition, it would have logically led to number two and number three on my list.
2. 2008 - Pirates DO NOT trade Jose Bautista to the Toronto Blue Jays.
This may be a bit of a stretch, but as a result of the Pirates drafting Posey instead of Alvarez, the Pirates see no reason to move current masher Jose Bautista. Reports suggest that Bautista arrived at his recent success thanks to Blue Jays coaching, but who knows. Back in the Pirates alternate universe, Bautista still loses his job to Jason Bay-trade chip Andy LaRoche, but regains it when LaRoche struggles. From there, he hits 124 homeruns in slightly more than 1700 plate appearances from 2010-2012 on his way to super stardom.
3. 2009 - Pirates select Mike Trout in the June draft.
This also may be a bit of a stretch, but with Buster Posey in the fold in 2009, the Pirates choose to go a different direction than Tony Sanchez with the fourth overall pick. Reports indicate that the Pirates did not feel there was a consensus player to take with the fourth pick, thus the selection of Sanchez. Therefore, the Pirates choose to reach anyway and select Mike Trout fourth overall, adding a future superstar to the organization.
4. 2011 - Pirates trade Joel Hanrahan for Jurickson Profar
In early 2011, the Rangers approached the Pirates seeking to add bullpen hope. They inquired on the availability of closer Joel Hanrahan, and the Pirates rebuffed them by asking for the young and highly touted pitcher Neftali Feliz. The Rangers understandably passed. No other details have been reported about those talks, but at the time Jurickson Profar was a fringe top 100 prospect struggling in the South Atlantic League early in the season. It's possible the Pirates asked about him and were rejected, or that the Rangers offered and the Pirates passed. Either way, or if he was never discussed, in this alternate universe, the Pirates trade Hanrahan for Profar.
5. 2011 - Pirates select Manny Machado in the June draft.
In the 2011 draft, Bryce Harper was the consensus number one overall pick and the Nationals did not stray from the consensus, taking the controversial outfielder to start off draft day. At number two, the Pirates were given the opportunity to pick between an elite prep pitcher and an elite prep shortstop. They chose the pitcher, Jameson Taillon. It was far from a bad pick; Taillon is a top prospect who should arrive in the majors soon. However, Manny Machado, the shortstop the Pirates passed on, has outpaced Taillon in both his prospect status and his expediency to the majors thus far. Had the Pirates selected Machado, he would be slated to start next year at third base next to Jurickson Profar in the infield, filling the absence of Pedro Alvarez.
If the Pirates could go back and switch their past, altering history in the five ways outlined above, here's what a potential 2013 lineup (The rotation probably wouldn't look much different, unless they Pirates looked at their lineup going into 2013 and decided to make a big trade for a pitcher or use the Russell Martin money to sign a free agent hurler).
1. Profar - Shortstop
2. Trout - Left Field
3. McCutchen - Center Field
4. Jones/Sanchez - First Base
5. Posey - Catcher
6. Machado - Third Base
7. Walker - Second Base
8. Marte - Right Field
Ya, that looks pretty good, hindsight twenty-twenty good in fact.