Dec 9th 1999 : Jeffrey Loria buys the Expos
Ok this is the 90s but forgive me if I go back 3 weeks to grab the goddamn trigger to the end of baseball in Montreal. The team had been dismantling before this, but that happens all the time. What doesn't happen all the time is teams being sold to a direct descendant of Satan. For example he would trade Ted Lilly for Hideki Irabu before the year was over. Only pure evil could do something like that.
April 2000 : Loria only signs to broadcast the Expos on radio... in French. (A deal to make these broadcasts only available in Laos fall through at the last minute.)
2000 : Public funding for a downtown Montreal park falls through. Montreal disappears from the map never to be seen again. (or continued to grow just fine economically, I forget which)
November 6, 2001 : MLB votes to contract by 2 teams while looking directly at Montreal and Minnesota. Why? Because Selig is a National Disgrace, remember? For those too young to remember, baseball owners wanted a way to flex their muscles over the player's union. So they voted for this and Selig hoped to sneak it through in 4 weeks. Maybe he though everyone would be on vacation? The Expos were dead men walking.
Dec 20th 2001 : MLB buys the Expos. In order for baseball to get the Expos so they could get rid of them, they pushed a deal for John Henry to buy the Red Sox with a higher offer on the table, they let Loria... well let's just read the Wikipedia line
Loria moved the entire Expos management and coaching staff, including manager Jeff Torborg, to Miami — leaving the Expos without personnel, scouting reports, and office equipment, including the team's computers.
September 2002 : Omar Minaya trades Grady Sizemore, Brandon Phillips and Cliff Lee for Bartolo Colon. For the defense, he thought the team would be gone. For the prosecution, reread the bold sentence.
2003: MLB decides Montreal will play 22 "home games" in Puerto Rico.
How does the man sleep at night? On a bed of dead puppies? The team does draw decently considering but still they were never going to move there so this was just Selig being a tease.
August 28th 2003 : Baseball decides it can't afford $50,000, otherwise known as A-Rod's Rolos budget, to call up minor leaguers. Really they just didn't want to take the chance the Expos might actually make the playoffs.
November 2004 : Baseball names Jim Bowden GM of the Washington franchise. Moving to DC can't be seen as a bad thing, but this decision surely was in retrospect. Bowden did not know how to build a minor league system (he would immediately lose two draft picks by signing Vinny Castilla and Christian Guzman unecessarily early), and was mediocre in his wheeling and dealing. This might have been fine if he were the silent type - but he was a segway-riding, drunk-driving, wife-fighting, "dawg"-spouting, questionable-situation-finding mess. He seemed to show some competence when later wrangled by Kasten, but "competent when controlled" is hardly the comment you want given as your GM's best quality.
March 31, 2005 : Baseball strikes a deal with Peter Angelos so that the Orioles will handle television and radio rights to the Washington franchise. The Nationals are the only major league team that doesn't own their own broadcast rights which will cost them millions down the road. MASN gets off to a real slow start and most of area can't see Nats on TV reguarly until 2007 season.
April - May 2006 : Nationals start the season 12-25, basically ending any hope for fans a mere 2 months into the season. This was in stark contrast to the amazing first half of 2005, but in itself wasn't terrible. What was terrible was they then started 2007 9-25, and 2008 5-15, and 2009 17-46. This is more of a single place to remark about all the terrible baseball that the Nats have played from 2006 on marked by a "best" season where the Nats won 73 games and finished 16 games out of first and most recently back to back 59 win seasons.
March 30, 2008 : The Nats opened their new stadium to a less than enthusiastic "meh". It wasn't a failure along the lines of most other things on this list but a new stadium should "wow". This one surely didn't. We hoped for better. The struggles to get the damn thing built lasted forever as MLB dug in its heels that it wouldn't (and future owners wouldn't have to) pay nearly anything for the stadium and the DC government slowly but steadily gave in. Then the Lerners wouldn't pay rent on it. They eventually tried to jazz it up but with no real views of the monuments, no giant baseball, cherry trees that don't stand out, odd looking statues... it's only ever going to be ok. Ok is not worth $611 million.
February 2009 : Sports Illustrated uncovers that "Smiley" Gonzalez is really 3 years older than what the Nats thought. And his name is really Carlos Lugo. And the Nats' representatives in the Dominican might have been skimming bonus money. And that includes their GM. And there is no Santa Claus. I guess you could say this was a good thing since it hastened the demise of Jim Bowden. I guess.
April 2009 : Adam Dunn and Ryan Zimmerman take the field with "Natinals" jerseys. Not in itself a horrible thing but just another in a long line of questionable little things the leadership did poorly in these first few years. Be it food issues at the stadium, issues getting season tickets, Screech, there always seemed to be something wrong both on and off the field.
There's been some hope that's all behind the team now. Next decade can't get here fast enough.