Sometimes it’s just not working.

It seems that every year we have struggling teams making moves with the future in mind. This year is no different, as there are a handful of squads in need of a complete roster rebuild.

Let’s take a look at a few of those organizations.

 

Cincinnati Reds 

On paper, the Reds are loaded with talent. Headlined by Johnny Cueto and Joey Votto, Cincinnati boasts a roster capable of causing some issues for the favorites in the National League Central. 

Cincinnati’s lack of any semblance of pitching depth will derail any postseason aspirations. 

A big reason for this is Cueto‘s impending departure this winter. The right-hander has recorded a sub-3.00 ERA in each of the past four seasons. Cueto will earn close to $200 million in free agency, a total the Reds aren’t likely to match. 

Homer Bailey and the recently acquired Anthony DeSclafani are under team control for the next few seasons, but the Reds will more than likely be looking to fill three spots in their 2016 rotation. 

Prospects Robert Stephenson, Michael Lorenzen, Raisel Iglesias and Nick Howard all have ability, but there’s no clear cut ace in that group. Stephenson is probably the best of the bunch, but Kiley McDaniel at FanGraphs compares his ceiling to that of Bailey’s. 

Offensively, the Reds are being built around Joey Votto, Billy Hamilton and Devin Mesoraco. Aside from these three, the rest of the lineup should be expendable in the right deal. 

Todd Frazier has turned into a productive major leaguer, but his contract is up after the 2016 season. At 29 and with a big payday coming, Cincinnati should consider shopping Frazier for young pitching. Due to his affordable deal, the 2014 NL All-Star may be the most valuable asset on the roster. 

Jay Bruce and Brandon Phillips could also help a contender, but their excessive contracts and diminishing production will make them harder to trade. Phillips is owed roughly $37 million over the next three seasons, while Bruce is pegged to make $24.5 million over the next two years, with a $13 million team option for 2017. 

This Cincinnati roster has reached its peak. With a handful of players that can still help contenders, however, a rebuilding effort may be easier than it seems. 

 

Philadelphia Phillies

The Philadelphia Phillies are currently in a similar situation. 

The Phillies have over $100 million invested in Ryan Howard, Chase Utley, Cliff Lee, Cole Hamels, Jonathan Papelbon and Carlos Ruiz. When you take into account the fact that the club’s Opening Day payroll was around $147 million, it’s evident that the Phils need a major overhaul. 

The problem with trading these players is the lofty dollar amounts still owed to them over the next few seasons:

Of the players mentioned, Hamels, Utley and Papelbon are the most likely to be moved. 

Hamels remains one of the top left-handers in baseball, despite a slow start in 2015. With the insane contracts being handed to free-agent hurlers, the $23.5 million owed to Hamels over the next four seasons actually looks quite affordable. 

The St. Louis Cardinals, Boston Red Sox and Los Angeles Dodgers presumably have the prospects to acquire Hamels, but it remains to be seen if any club will be willing to pay the steep price the Phillies are demanding. 

Utley will be a free agent after the season, but there have been conflicting reports on how receptive he would be to a potential deal. ESPN’s Buster Olney has reported that many teams have been told that Utley has no intention of leaving Philly. Olney pondered if Utley’s stance could be changed:

Over the past year, other teams have been told that Chase Utley will not accept a trade out of Philadelphia. But there is some curiosity about whether this will change, in the face of the Phillies’ dim prospects now or in the immediate future. Jimmy Rollins chose to leave, accepting a trade to the Dodgers, and rival evaluators believe Cole Hamels wants out as well.

Last but not least, the $13 million remaining on Papelbon’s deal this season has deterred interested teams. The right-hander told CSN Philly that he would be disappointed not to get traded this season. Papelbon has remained productive and could bolster a team’s bullpen.

By trading Hamels, Utley and Papelbon, the Phillies would surely add to their 21st-ranked farm system

 

Milwaukee Brewers 

The future may look bleak for both the Reds and Phillies, but it’s not nearly as bad as the debacle in Milwaukee.

The Brewers have begun the 2015 season with a 4-16 record. With Jonathan Lucroy and Carlos Gomez on the DL, it may be time for the Brew Crew to blow up its current roster.

Milwaukee ranks 19th in Baseball America’s organizational talent rankings, but you won’t find a pitcher until the No. 7 overall prospect. Jimmy Nelson has cracked the major league roster and is impressing to begin the season, but he is the extent of the promising pitching talent. 

What can the Brewers do to bring in additional young arms? It may be unpopular, but parting ways with the talented Gomez would be a start. 

Gomez is under team control through 2016 and owed only $17 million over the next two seasons. That’s a bargain for a player with 27 homers and 74 steals over the last two seasons. Gomez is affordable, under contract and productive. 

Kyle Lohse and Jean Segura are other free-agents-to-be at the end of the season and present some value for interested teams. Lohse has posted a sub-4.00 ERA every season since 2011, while Segura is hitting over .300 to begin the season.

A lack of any pitching depth throughout the organization is a scary truth with which Milwaukee fans are starting to come to grips. It’s a serious issue that needs to be addressed before Milwaukee can return to the playoff picture.

Read more MLB news on BleacherReport.com