If the owner of your favorite baseball team has a “win at all cost” attitude, that’s usually a good thing, right? Yes! Being aggressive and spending money has paid off for many eventual World Series champions. But it’s also resulted in some very dire situations, notably in the case of Arte Moreno and the Los Angeles Angels

Saddled with two of the worst contracts in baseball—Albert Pujols, whose numbers have declined in three consecutive seasons, is still owed $212 million through his age-41 season in 2021; Josh Hamilton, also in the midst of his worst big league season, is due $106 million through his age-36 season—the Angels are headed for an extremely important offseason that is likely to be challenging in terms of a limited payroll and limited trade pieces in the minors. 

General manager Jerry Dipoto, assuming he still has a job after a very disappointing season, will have to be creative if he wants to improve this ballclub.

It’s hard to do any worse than he did last offseason, when he took on the risk of signing Hamilton, signed Joe Blanton to a two-year, $16.5 million deal—Blanton was recently banished to the bullpen after pitching poorly out of the rotation—and acquired Tommy Hanson from the Braves for reliever Jordan Walden—Hanson was recently optioned to the minors while Walden has been a key component on a very good Braves team. 

In addition, Dipoto‘s two big bullpen acquisitions haven’t worked out due to injuries—Ryan Madson never made it back from Tommy John surgery before being released; Sean Burnett has pitched just 9.2 innings and is out for the season with an elbow injury. And to cap it off, Ervin Santana, who was traded to Kansas City for a 27-year-old minor league relief pitcher, has been Cy Young-caliber in 2013. 

Pointing out the few minor roster moves that have worked out won’t make things look much better. In order to make the Angels a playoff contender once again in 2014, they’ll need to utilize the few resources they have and get as much value out of them as possible. 

Despite the overall struggles of the pitching staff, three-fifths of the starting five—Jered Weaver, C.J. Wilson, Garrett Richards—are pretty solid. Fixing the back of the rotation on a limited budget isn’t impossible.  

Making up for Pujols’ decline and the production he’s given them versus what they’re paying him is the bigger challenge. Here’s my suggestion on how they can make up the difference on a shoestring budget and with no farm system talent to deal.

Trade Howie Kendrick to Free Up Salary and Clear Spot For Grant Green

Could it be that Dipoto fleeced the division rival A’s by trading a light-hitting third baseman for a guy with the potential to be a very good one? Grant Green (pictured), who was drafted as a shortstop and has played all over the diamond before settling into second base this season, has been on fire (14-for-51, 2 2B, 5 BB) since being acquired for Alberto Callaspo at the trade deadline. 

Callaspo is doing a fine job in a part-time role with Oakland (.785 OPS in 17 games), but he was miscast as an everyday third baseman in Anaheim, and the Angels needed to shed his $4.875 million salary for 2014.

Not only will they save close to $19 million over the next two seasons by trading away Kendrick, but they could also add a starting pitcher or a couple of prospects in the deal—it’s tough to find a match for a team in need of a second baseman and that is willing to give up a quality third baseman in return. 

Trading Kendrick to the Dodgers, who were reportedly in talks with the Angels last month regarding the second baseman, according to Ken Rosenthal of Fox Sports, could be revisited. While top pitching prospect Zach Lee was part of the trade package being discussed, there’s a chance that the insistence of his inclusion might be the reason why the deal didn’t happen. 

If the Angels took back Stephen Fife (2.47 ERA in nine MLB starts) instead to fill the fifth spot in their rotation and asked for the team’s top outfield prospect, Joc Pederson, who likely won’t make it to the majors on a Dodgers team deep in outfield talent, we could have a deal.  

Trade Peter Bourjos for Chase Headley

With Pederson on board, the Angels would be free to shop Peter Bourjos with Mike Trout moving over to center field. While he’s been injured for much of the season, the 26-year-old Bourjos has been productive when on the field. 

In 45 games, Bourjos has a .780 OPS with three homers and four stolen bases. If he can stay healthy, a team could get a terrific defensive center fielder with an ability to hit 10-15 homers and steal 25-30 bases. With third base the target, the Angels need to find out if the Padres are interested in three seasons of Bourjos—he won’t be a free agent until after the 2016 season—in exchange for one season of Chase Headley (pictured).

While the Padres already have an injury-prone Cameron Maybin signed long-term to play center field in San Diego, adding another speedy outfielder like Bourjos could still be a possibility.

Here’s why. The Padres have likely figured out that oft-injured Carlos Quentin isn’t capable of holding up for an entire season in the National League. Moving him to an American League team that will be able to place him in the designated hitter role for a majority of the time makes a lot of sense. They’ll need an outfielder to replace him, and that’s where Bourjos fits in. 

With an alignment of Maybin, Bourjos and Will Venable, the Padres’ outfield defense could be one of the best in baseball. Losing Headley and Quentin will leave a huge hole in the offense, but neither player factors into the future plans of the team. How they replace the loss of offense in 2014 is another story. 

As for the Angels, they might have to include a mid-level prospect to get the deal done, but the 29-year-old Headley‘s value has plummeted with his subpar season. It might not take much to get him. His projected $9-10 million salary for 2014 is likely affordable with Kendrick and Callaspo off the books.

Sign Eric Chavez in Case Pujols Misses Time

A native San Diegan, Eric Chavez (pictured) could get closer to home by signing with the Angels this winter after two consecutive productive seasons (.855 OPS, 25 HR in 2012-13) as a part-time player for the Yankees and Diamondbacks.

Because the 35-year-old still can’t shake the injury-prone tag—he’s been on the disabled list multiple times over the past few seasons—coming back to the American League is likely so he can log at-bats from the designated hitter spot. It’s also the reason his salary demands will stay low enough for the Angels to afford him and the reason he won’t be offered a full-time starting gig elsewhere. 

Resulting Lineup Projection

1. Mike Trout, CF
2. Chase Headley, 3B
3. Albert Pujols, DH
4. Josh Hamilton, RF
5. Mark Trumbo, 1B
6. Joc Pederson, LF
7. Grant Green, 2B
8. Erick Aybar, SS
9. Chris Iannetta, C

Hank Conger, C
Eric Chavez, 3B/1B
Andrew Romine, IF
J.B. Shuck, OF

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