White Sox swing and miss on Zack Wheeler, Cole Hamels

Zack Wheeler

White Sox general manager Rick Hahn has said the team intends to sign two free agent starting pitchers this offseason. However, two pitchers the Sox were linked with signed elsewhere Wednesday.

Zack Wheeler agreed to a five-year, $118 million contract with the Philadelphia Phillies, while Cole Hamels joined the Atlanta Braves on a one-year, $18 million deal.

According to a tweet from MLB Network's Jon Heyman, Wheeler was the Sox's top target in terms of starting pitchers. Apparently, the Sox front office doesn't believe it can land either Gerrit Cole or Stephen Strasburg, the two elite aces on the market, so the Sox set their sights on the best pitcher in the "second tier" of available starters.

That would be Wheeler, but as per usual, the Sox are the bridesmaid and not the bride. The Phillies beat out the Sox, the Minnesota Twins, the Cincinnati Reds and the Texas Rangers in this pursuit.

According to a tweet from MLB Network's Ken Rosenthal, the Sox's offer to Wheeler was for *more* than $118 million, but Wheeler's wife is from New Jersey and proximity was important.

OK, not sure if I buy that. It's all speculation, but for me as a Sox fan, the bottom line is the Hahn regime continues to come up short far more times than not, and the team still has much to prove in terms of its commitment to winning.

As for Hamels, just days ago he was on the White Sox Talk podcast with NBC Sports Chicago's Chuck Garfien to express his interest in possibly coming to the South Side.

Instead, Hamels will be headed to Atlanta. This loss isn't as big of a deal for the Sox, but let's be honest, Hamels would have been a nice fit as a veteran left-hander in the middle or the back of the rotation.

If the Sox are not in on Cole or Strasburg, and we have to assume they are not until proven otherwise, where does the team go from here? Do they pursue Madison Bumgarner? Dallas Keuchel? Someone else?

The Sox front office continues to earn skepticism from me. I'm not convinced they are going to land the two starting pitchers they need. C'mon, guys, prove me wrong.

Can Chase Headley jump-start the Yankees in the AL East race?

The New York Yankees have a mediocre 51-48 record and a minus-30 run differential, and 80 percent of their projected starting rotation is on the disabled list.

Nevertheless, the Yankees still believe they have a shot to win this year, and they signaled as much on Tuesday when they acquired third baseman Chase Headley from the San Diego Padres in exchange for infielder Yangervis Solarte and minor-league pitcher Rafael De Paula.

You can't blame the Yankees for believing they have a chance. The AL East is no longer the strongest division in baseball. Despite its uneven play, New York sits just four games back of first-place Baltimore entering Wednesday's action.

But can Headley make an impact? The numbers suggest he will not. He has experienced a steady decline since his career year in 2012.

2012: .286/.376/.498, 31 HRs, 115 RBIs
2013: .250/.347/.400, 13 HRs, 50 RBIs
2014: .230/..296/.353, 7 HRs, 33 RBIs

There's nothing about Headley that suggests he will ever repeat his numbers from two years ago. That was a career outlier. His career slash is .266/.346/.409. He's perhaps a better hitter than he's shown this year, but it's folly to think he'll ever slug close to .500 again.

Headley has been floundering on some awful San Diego teams. He has no help in that lineup whatsoever, so there is some chance he will be resurgent in New York where he will no longer be counted upon to carry an offense. Some have noted Headley's numbers might be hurt by the pitcher-friendly confines at Petco Park. Yankee Stadium, of course, is a hitter-friendly ballpark.

However, an analysis of Headley's splits this year shows no difference in his slugging percentage home and away:

Home: .250/.301/.354, 2 HRs, 19 RBIs
Road: .209/.290/.353, 5 HRs, 14 RBIs

Headley has been a slightly better offensive player at home, in fact. I'm skeptical he'll be the game-changer the Yankees are looking for.

What New York really needs to do is add a front-line starting pitcher. The Yankees have had horrible luck this year with Masahiro Tanaka, CC Sabathia, Ivan Nova and Michael Pineda all on the disabled list. The latter three are on the 60-day DL. Brandon McCarthy has made two good starts since coming over from the Arizona Diamondbacks, but the Yankees are at least one arm, if not two, short in the starting rotation.

There are rumors the Yankees are interested in White Sox left-hander John Danks. I would think, though, that New York needs a top-of-the-rotation starter, like Cliff Lee or Cole Hamels. Danks is nothing more than a mid-rotation guy pitching with a surgically repaired shoulder at this point.

Even with Headley, I don't think New York is going to win the AL East as presently constructed. I think the Yankees need that guy to lead their pitching stuff, or else they'll be lucky to stay in the hunt for the wild card in a mediocre American League.

Big contract for any pitcher is risky business

The contract Japanese pitcher Masahiro Tanaka is going to receive is already giving some people upset stomachs. The size of it might end up being more eye-popping than the $50-60 million contracts teams gave to Yu Darvish and Daisuke Matsuzaka. Keep in mind that was before the posting fee was capped at $20 million. The Red Sox and Rangers each coughed up posting fees in excess of $50 million, making the total investment for each pitcher more than $100 million.

It was a big deal when Kevin Brown
became the first $100 million pitcher
in baseball when he signed with the Dodgers.

That big of an investment rarely works out well if you're expecting the player to pitch well over the life of the whole contract. Here are the biggest contracts ever given to pitchers:

Felix Hernandez, Mariners, $175,000,000 (2013-19)
CC Sabathia, Yankees, $161,000,000 (2009-15)
Zack Greinke, Dodgers, $147,000,000 (2013-18)
Cole Hamels, Phillies, $144,000,000 (2013-18)
Johan Santana, Mets, $137,500,000 (2008-13)
Matt Cain, Giants, $127,500,000 (2012-17)
Barry Zito, Giants, $126,000,000 (2007-13)
CC Sabathia, Yankees, $122,000,000 (2012-16)
Mike Hampton, Rockies, $121,000,000 (2001-08)
Cliff Lee, Phillies, $120,000,000 (2011-15)
Yu Darvish, Rangers, $111.700,000 (2012-2017)*
Kevin Brown, Dodgers, $105,000,000 (1999-2005)
Daisuke Matsuzaka, Red Sox, $102,111,111 (2007-2012)*
Adam Wainwright, Cardinals, $97,500,000 (2014-18)
Carlos Zambrano, Cubs, $91,500,000 (2008-12)
-Source: Cot's Baseball Contracts
*posting fee included with salary

Obviously most of these contracts are newer as teams have been flush with cash and the pay for elite pitchers has gone up. Though maybe it's interesting is that five of the top six contracts ever given out to pitchers weren't signed by free agents, but were extensions for guys with a year or two left before hitting the market.

Of the contracts that have been completed, all of them looked like a disaster at some point. Hampton's looked like one almost as soon as the ink dried in the thin Colorado air. Zito's was almost as bad save for the fact he still soaked up a lot of innings for the Giants over the course of his seven-year deal.

Over the course of Zambrano's extension, he suffered a decrease in either his performance or ability to take the mound each and every year of his new contract. Matsuzaka and Santana each had a few good years at the front ends of their deals before ineffectiveness and/or injuries did them in.

The best contract of all of them in my opinion was Brown's. Baseball's first $100 million arm was good for more than 1,000 innings with a 3.23 ERA over seven years. Brown, who I think has an underrated Hall of Fame case, missed some time with injuries, but still pitched a lot of mostly good innings for his money, only completely losing it the final year when he was 40.

The jury is still out on the other contracts. Cain, Verlander, Hamels and Sabathia each just endured their worst season in years. Greinke was very good, but missed time after breaking a bone in a scuffle with Carlos Quentin. With Hernandez, Lee, Darvish and Wainwright, things are looking so-far-so-good, though only Lee's contract is even close to completion.

The results here seem pretty apparent. If you don't have to spend almost $100 million or more on a pitcher, then don't. The risk is still one that teams are willing to make, especially teams that are close to contention. Should they be?

Possibly. In a way, this is already how teams view the cost of dabbling in free agency. They're willing to get a good value on the front end of a contract in exchange for dead money at the end.

Looking at each of these contracts, none of them really stopped the team paying the checks from doing anything else. Zito didn't keep the Giants from winning two World Series titles. Lee and Hamels aren't the problem with the Phillies' payroll. Even Mike Hampton's contract was eventually carved up and served in digestible bites that teams other than the Rockies helped swallow.

Unless Tanaka pulls a Hampton-Zito, the team that wins the bidding for his services will be getting a good pitcher for at least a few years. So any team with the money might as well bid away.