For the Baltimore Orioles, the 2018 regular season can not end soon enough. The team is 40-98 overall and on pace for 115 losses, which would put them among the worst teams in baseball history.

Here are the five losingest teams in the history of the sport:

  1. 1899 Cleveland Spiders: 20-134
  2. 1962 New York Mets: 40-120
  3. 2003 Detroit Tigers: 43-119
  4. 1916 Philadelphia Athletics: 36-117
  5. 1935 Boston Braves: 38-115

The 2018 Orioles have already earned the dubious distinction of being eliminated from the division race (Aug. 10) and postseason race (Aug. 20) earlier than any other team since the divisional era began in 1969. Now they're trying to avoid becoming one of the five losingest teams in history.

Give the Orioles credit though. They did not hold back at the trade deadline. Impending free agents Manny Machado, Zach Britton, and Brad Brach were all traded away. Players with team control remaining like Jonathan Schoop and Kevin Gausman were traded away as well. All told, the O's traded away six players and 15 prospects -- 15 prospects! -- were imported. Baltimore needed farm system help and they got it. They'll get more when they pick first overall in the 2019 amateur draft next June.

The Orioles have 24 meaningless games remaining this year, then they'll head into the franchise's most important offseason in quite a long time. They are very early in their rebuild and some important decisions have to be made, and not just at the player level.

Who stays and who goes among management?

Buck Showalter and Dan Duquette are both unsigned beyond this season. USATSI

Both executive vice president of baseball operations Dan Duquette and manager Buck Showalter are on expiring contracts, and their futures are very much up in the air. Brady Anderson, the team's vice president of baseball operations, is a favorite of owner Peter Angelos and has serious way in the organization. Angelos is 89 now, however, and his sons John and Louis have assumed more responsibility within the organization.

Showalter has been tight-lipped about his future. He so clearly (and dearly) loves the game and loves to manage, but, at age 62, he may not want to wait out a long rebuild with the Orioles. MLB teams are gravitating toward younger (and cheaper) managers and Showalter is still looking for that elusive World Series ring. Other teams closer to contention could come calling this offseason (Angels? Nationals?) and may be more appealing to Showalter than the 100-something loss O's.

The larger question here is with Duquette and the front office. Does Angelos (and his sons) want Duquette? Does Duquette want to come back? Is it time for Anderson to take over as the head decision-maker? Is it time to wipe the slate clean -- the O's could hardly be blamed for that after this season -- and bring in a fresh set of eyes and ideas? A firm front office structure with a clear chain of command must be put in place. The rebuild can not begin in earnest until that happens.

It seems to me the front office question must be answered before the Showalter question. Keep in mind this would not be a normal "new front office inherits an incumbent manager" situation. That happens all the time. In this case, the Orioles would have to re-sign Showalter and foist him upon the front office. If there is going to be a new front office -- that is hardly set in stone -- shouldn't they be given the opportunity to bring in their own coaching staff?

Righting the ship after such a dismal season is a process that starts at the top of the organization. It's not as simple as signing some free agents and making some trades, changing the roster, and going from there. The Red Sox and Yankees are powerhouses and the Rays are up-and-coming. A few roster tweaks won't turn things around. Deeper change is required. The Orioles have to figure out who they want in charge going forward. That is priority No. 1 this offseason.

Who stays and who goes among players?

MLB: Boston Red Sox at Baltimore Orioles
Reliever Mychal Givens might be the most valuable trade chip remaining on the O's roster. USATSI

There aren't many tradeable players remaining on the roster following the trade deadline. Adam Jones will be a free agent this winter and Chris Davis is virtually immovable thanks to his contract. Unloading Mark Trumbo might take some creativity. Dylan Bundy and Mychal Givens represent two young pitchers under team control with actual trade value who could net the team more prospects. Andrew Cashner, Alex Cobb, and Jonathan Villar might be able to fetch something as well.

This is the scary thing for the Orioles: When you look at their active roster, it's hard to find many players with a chance to be part of the next contending Orioles team. Rookie center fielder Cedric Mullins? For sure. I like catcher Chance Sisco and really like hard-throwing southpaw Tanner Scott as well. After them, there aren't many long-term building blocks on this roster. The O's really are starting from the ground up here.

Baltimore's farm system is improved thanks to the trade deadline. Outfielder Yusniel Diaz (Machado trade) and third baseman Ryan Mountcastle, the team's two top prospects, should arrive next year. Outfielder Austin Hays, last year's minor-league breakout star, should be in better position to contribute in 2019 after dealing with injury after injury this summer. There is some help on the way. Those guys (and others) will break in next year. 

For now, the O's are running out the clock on the 2018 season without much promising young long-term talent on the roster. There's Mullins, Sisco, Scott, and maybe someone like Trey Mancini or Josh Rogers if things go right. If the selling continues this winter, it'll involve guys like Bundy and Givens, and maybe Cashner, Cobb, and Villar. Otherwise there aren't many veterans with actual trade value on the roster.

How can they fix their player development?

MLB: Baltimore Orioles at Atlanta Braves
Dylan Bundy is good, but not fourth overall pick in the draft good. USATSI

Specifically their pitcher development. The Orioles have done quite well on the position player side. Machado became a megastar, Schoop was a quality everyday player, and Mullins looks like a real deal. Things have not gone as well on the mound. Check out the last five pitchers originally signed and developed by the Orioles to post a +4 WAR season with the team:

  1. Kevin Gausman, 2016: +4.1 WAR
  2. Zach Britton, 2016: +4.2 WAR (as a reliever)
  3. Erik Bedard, 2007: +5.7 WAR
  4. Mike Mussina, 2000: +5.7 WAR
  5. Mike Mussina, 1999: +4.4 WAR

Oof. That's three homegrown starters this century with a +4 WAR season and one (Gausman) only barely reached that modest threshold. Pitcher development must improve. The O's had success in recent years with guys like Chris Tillman (Bedard trade) and Jeremy Guthrie (waiver claim). Now they have to figure out a way to crank out their own quality starting pitchers.

How do the O's go about fixing their pitcher development? That's close to impossible to answer for someone outside the organization, though it does tie back to the question about the front office. If the Orioles retain Duquette and keep things relatively status quo, why would you expect things to change drastically? That isn't to say they can't fix their pitcher development under Duquette, but it will take change at some level. Maybe they need new coaches or new analysts.

The inability to develop top pitching talent into big-league contributors has been an organizational weakness for almost three decades now. You have to go back to Mussina, a should-be Hall of Famer, to find the last consistently above-average starter drafted and developed by the Orioles. This is not a short-term problem. It is a long-term issue spanning several front office regimes. Correcting it should be the top priority going forward.

The 2018 season has been a miserable failure for the Orioles, so much so that they've already set two records for futility given their early division and postseason eliminations. And without guys like Machado, Schoop, and Britton around for the final month, it is entirely possible the O's will flirt with 120 losses this season. The 2018 O's are, rather easily, the worst team we've seen since the 2003 Tigers.

If there is any good that can come from bottoming out in the standings like this, it's that ownership could hand the organizational keys over to a new front office regime, even if that regime is led by a holdover like Brady Anderson. The Orioles collapsed this year and some level of change is warranted, starting at the top, with the key decision-makers. The 2018 Orioles are nearly as bad as the 2003 Tigers, and as bad as the Tigers were that year, remember they went to the World Series in 2006. The turnaround doesn't necessarily have to take long.