January — The Pirates kicked off their Winter Caravan the day Kevin McClatchy turned 45 (January 13th) by visiting Seven Springs, but nobody showed up for the party. Having sold just 2,000 season ticket packages by January 18th, Robert Nutting ordered more salary dumps which led to Jason Bay, Jack Wilson, Damaso Marte, and Adam LaRoche being traded to the St. Louis Cardinals for Matt Clement and Rick Ankiel. Piratefest was canceled due to a blizzard.
February — Spring training opened and problems at the new facility were immediately obvious – Ian Snell didn’t have a locker, each of the Fields had new names taken from the Nutting’s grandchildren causing a lot of confusion, there were only two urinals in the clubhouse, and the players were nearly ready to strike until John Wehner stepped in and told the chef if he didn’t stop serving veggy plates for lunch, he’d knock his socks off.
March — Fearing for their lives from viruses transported by monster-sized mosquitoes, the New York Yankees hired 10 rent-a-drunks and put them in Yankee uniforms to play against the Pirates March 19th – the first full squad game under the lights at McKechnie Field. More than 100 fans in attendance were hospitalized with 40 or more welts the size of a half-dollar on their faces. Camp broke with Sean Burnett as the 5th starter despite throwing 75 mph.
April — The Pirates ended up playing just 11 games in April because all the players had pneumonia from opening in Atlanta in 30 degree temps, flying to Miami to play in the 80’s, then back to Pittsburgh to play in the teens with blowing snow. They got out of the hospital in time to fly to Los Angeles to play in the 90’s, went to Chicago to play in the teens again, and then all ended back in the hospital with a relapse of pneumonia.
May — After finally winning just their first game of the year against the Nats, the Pirates played 36 games over 24 days finishing the month with a two-month record of 3-43 – the worst losing streak opening the year in the history of the franchise. Season ticket holders sued the Pirates for pain and suffering, and the players sued for better working conditions after the Pirates were forced to play 10 games in monsoon rains with field puddles up to their knees.
June to the AS break — The Bucs played 41 games in 35 days and all the starting pitching ended up on the DL except for Zach Duke, who ended up 2-9 in the first half, and Matt Morris, who went 3-7. After being shutout 12 consecutive games against the White Sox, Jays, Yankees, and Rays, plus taking a draft pick who he could meet slot with, Frank Coonely was fired and Chuck Greenberg hired to take over. The team finished 18-70 at the break, Ian Snell was institutionalized for a mental breakdown (all he would say is "I can’t believe it, I can’t believe it"), and Rick Ankiel led the team in home runs with 8.
July trade deadline — Greenberg ordered Huntington to dump every player making more than the minimum in exchange for the best talent he could get, to bring Andrew McCutchen, Bryan Bullington, and Neil Walker up, and after the game on July 31st held a closed-door meeting with the players. When Greenberg appeared from the meeting in front of media, he handed Neal Huntington his walking papers. Tony LaCava was hired as GM the next day.
August — The fired up Bucs start winning behind Walker and McCutchen who were both hitting over .400, Oliver Perez and Kris Benson are both brought back since they were begging to play for Greenberg, and Chris Duffy came out of the closet admitting he’s really a right-hand batter who was forced to hit lefty because the Pirates demanded that from him.
September — Pirate fans pack PNC for the last 10 games at home and the players respond putting on a show winning every single game from that point forward to close the season 82-80 fending off the club’s 16th consecutive losing season. The Pirates finished third in the division.
October — LaCava wastes no time in putting together his club for 2009 bringing in Tom Kotchman as bullpen coach, Perry Hill as first base coach, Trent Jewitt is brought up as third base coach, and Bob Walk was hired as pitching coach. LaCava gets so many calls from people wanting to join his club he has to change his cell number. After firing nearly every pro scout and special assistant except Pete Vuckovich and Jack Bowen, LaCava revamped the entire scouting department and John Wehner was hired as Player Development Director.
November — Greenberg and LaCava were handed the keys to the City for their achievements, and they entered the GM meetings looking to deal. Pirate fans continued to flock to the park two months after the season ended hoping to get a glance of the now famous duo.
December — After much speculation, Robert Nutting sold the club to Mark Cuban the day before Christmas declaring that "God told him to." Cuban announces on Christmas day the payroll would be set at $120M in 2009 and more than 25,000 season tickets are sold before the end of the year.