May 1, 2013; Chicago, IL, USA; San Diego Padres third baseman Chase Headley (7) is congratulated by left fielder Carlos Quentin (18) for hitting a home run against the Chicago Cubs during the ninth inning at Wrigley Field. Cubs beat the Padres 6-2. Mandatory Credit: Rob Grabowski-USA TODAY Sports

The Padres have been playing much better baseball lately. They’ve won eight of their last eleven games and only sit five games off the pace in the NL West race. Outside of Clayton Richard, the starting pitching has stabilized and the offense has done enough to keep them in most ball games.

Last week, it was reported that Padres’ ownership was prepared to offer slugger Chase Headley a “record deal,” an offer that would be the biggest in the history of the franchise. However, Headley quickly came back and said that he would not negotiate a long term contract during the midst of the season, but would be happy to work out a deal during next off season.

If Headley is true to his word, this puts the Padres in a very tricky situation moving forward. They will either have to wait until the off season to discuss Headley’s long term future with the club (and risk not getting a deal done and have Headley walk to free agency, in which case the Padres would virtually lose him for nothing) or hedge their bet and trade Headley now while they can still get value back in return.

Headley is under team control through the 2014 season, which makes him an even more desirable 3B option for a pennant-seeking team. Coupled with the fact that it’s a very weak third-baseman market out there, the Padres would likely be able to get a “Latos-like” haul back for Headley if they decided to trade him before the July 31st trade deadline.

But what kind of message would that be sending from an ownership group that has promised change and has said they want to keep franchise-type players in San Diego?

The fan-base still does not trust this organization. Whether it’s controversial comments from President and CEO Tom Garfinkel, the on going Time Warner Cable fiasco, or trading away cornerstone players such as Jake Peavy, Adrian Gonzalez and Mat Latos (albeit under the old regime), the Padres have struggled with a PR image over the past several years. Shipping off Headley would be another huge blow to any hope of getting back in the good graces of the San Diego community.

While Headley is currently making around a-fairly-reasonable $8 million per year, he’ll likely get a significant salary bump if and when he hits free agency in the winter of 2014. If he gets to that point, the Padres would almost certainly get out-bid by another organization for Headley’s services.

Headley has said he won’t negotiate a long term deal during the season. However, he didn’t say he wouldn’t sign a deal during the season. So in my mind, the Padres should offer Headley a deal that he literally cannot refuse. Take away the negotiation piece. He said he wants to stay in San Diego. Ownership has said they want him to stay in San Diego. So advice to ownership: make it happen and stop making empty promises.

Otherwise, the Padres will find themselves in another lose-lose situation with the fan-base and will have to again explain why a franchise player was traded or let go just because they didn’t want to pay him market value.

May 2, 2013; Chicago, IL, USA; San Diego Padres shortstop Everth Cabrera (2) hits an RBI single during the eighth inning against the Chicago Cubs at Wrigley Field. Mandatory Credit: Reid Compton-USA TODAY Sports

After losing the first game of the four game series at Wrigley Field against the Cubs on Monday night, the Padres managed to take two of the final three games to earn a split. The Padres now head back home to face the Arizona Diamondbacks for the first time all season, followed by a three game series against the Miami Marlins.

Some observations from the series with the Cubs.

Too many strikeouts

During the four games in Chicago, we saw flashes of both the old Padres offense that struggles to score runs at times, and also a glimpse of what the offense is capable of when they are able to string some hits together. While the offense is certainly improved from past Padre teams, they still strike out too much. And it’s not just the sheer number of strikeouts (although that can certainly be improved), it’s when they occur. I alluded to this in my post from Monday, but the Padres are in the lower tier of the league with runners left on base. Much of that comes from swinging and missing at inopportune moments. During the four games against the Cubs, the Padres were rung up 38 times. I watched all four games pretty intently; I cannot tell you how many times the Padres had a chance to drive in a run or, at the very least, extend an inning, and the guy at-bat struck out. They need to improve on getting the ball in play, and putting more pressure on the defense.

A perfect example of this happened earlier today in the series finale, and it sparked the big 8th inning rally. Yonder Alonso popped a ball up to shallow right field.  From there, the Chicago wind took over, making a routine inning-ending play an adventure in the outfield. The ball dropped in, a run scored, and the rest of the two-out rally is history. Put the ball in play, and good things will happen.

Ex-Padres continue to burn SD

One of the big storylines coming into this series was Anthony Rizzo going up against the Padres. The Padres received Rizzo from Boston in the Adrian Gonzalez trade, and then proceeded to flip him to the Cubs after getting Yonder Alonso in the Mat Latos deal. While Rizzo was held relatively in-check during the series (4 for 12 with only one RBI), Padre fans can’t feel too good about seeing his 8 HRs and 20 RBIs in the month of April alone, while Andrew Cashner, the fire-ball pitcher the Padres received for Rizzo, still floats between the rotation and the bullpen and is struggling to find an exact role on the team.

In addition to Rizzo, Cody Ransom, who the Padres let go just two weeks ago, seemed to make big play after big play in this series, particularly on Monday night, when he hit a huge home run and made a key defensive play at third late in the game. Scott Hairston, who spent several years in a Padre uniform in the late 2000′s, hit two homers in the series, including what looked to be the game-winning home run in Thursday afternoon’s contest, until the Padres scrapped and clawed for four runs in the 8th inning to take the lead for good.

Cashner’s first start was sub-par

To say the least. He looked terrible on Wednesday night. Probably a little over-amped to face his former team, he only lasted 4 innings, giving up 5 runs, 6 hits and 4 walks. Cashner had zero command of his pitches, as he looked uncomfortable on the mound virtually the entire 4 innings of work. It looks like Cashner’s spot in the rotation is set for now, which will hopefully allow him to relax his next time out against Miami. With a Stanton-less Marlins squad back at the friendly confines of Petco Park, I’m willing to bet Cashner throws a gem on Monday.

Quick hits

It was good to see Jedd Gyorko get off the schnide and hit his first home run as a big-leaguer. I think you will see a different Gyorko for the rest of the year than we saw in April.

What is wrong with Clayton Richard? A few more bad starts and he could find himself out of the rotation.

Everth Cabrera is the most productive player on the team right now. He is playing very solid defense and he’s getting on base.

I’ll have more to say on the Chase Headley extension talks in my next post or two, but I am cautiously optimistic that they will get a long term deal done before the trade deadline.

For awhile, I convinced myself to be content with the Padres holding on to their bullets. There is no need to blow up your entire farm for one player, especially if that player does not convert the team from pretender to contender. But then Keith Law’s Top 100 Prospects for 2013

“What? I’m only gone 50 games.” Mandatory Credit: Mark J. Rebilas-USA TODAY Sports

was released and my mind completely flipped. Six Padres were listed, four are carry overs from 2012. Their 2012 ranking is in parenthesis.

36. Austin Hedges

51. Max Fried

54. Rymer Liriano (40)

60. Casey Kelly (32)

70. Jedd Gyorko (90)

88. Joe Ross (49)

Players ranked last year all went down a few spots except for Gyorko, who is arguably our most sought out prospect. But what do these rankings mean? What percentage of the guys ranked between #50 and #60 become major contributors on a big league team? Whats the probability all of them becoming everyday starters?

I have no answer to any of those questions, but I did come to a conclusion.

Since 2010, Kelly has gone from #18 on Law’s list down to #60 where he sits today. He got a few starts with the Padres, albeit prematurely, and looked OK. He was always projected to be, at best, a #2 starter in the rotation but more likely a #3 guy.

You know who else was ranked around #60 not too long ago? Simon Castro. I do not want to compare but I do want to point out the delicacy of these rankings. Castro was ranked #64 on Law’s list in 2011. We moved him to Chicago in the Quentin trade. Castro still has not been called up.

Jaff Decker was ranked #50 on MLB.com’s Jonathan Mayo list of top 50 prospects  in 2010.  In 2011, he was #46 on Keith Law’s list. He has since been leapfrogged by our current set of highly touted prospects.

Unless you have a guy like Jason Heyward, Mike Trout, Stephen Strasburg, guys consistently listed #1 or #2 on EVERYONE’S list, they’re not a sure thing.

In the Peavy deal, we acquired the two best pitchers in the White Sox’s  system in Aaron Poreda and Clayton Richard. Poreda was suppose to be a stud. He’s not even on our team anymore. Three of the four players we received in the trade are not on the team.

That is how delicate and hard gauging prospects is. A sure thing can always blow up in your face and all of a sudden you are left without an ace on the staff. Even the Latos trade took a knock with the Grandal suspension.

If Byrnes had a deal on the table set for Stanton or Upton, the trigger needed to be pulled. Both are proven players and are only going to get better. Holding on to prospects and rejecting trades for players ready to play now will leave the Padres selling us the team on potential. “Yeah we’re 35-64 but look at all the high-ceiling draft picks on the field.” Is that what you want to hear in 2 years?

Why do we have to be the team that sits on prospects when we have the bullets to be firing away and taking proven talent from teams? We’re still getting a feel for our new front office but Byrnes being gun-shy for a player of Stanton or Upton’s caliber leaves me wondering if banking on our highly ranked farm wont blow up in our face.