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10 Degrees: Kevin Youkilis deal opens what could be a fascinating trade season

Jeff Passan
Yahoo Sports

This divorce went like all the others with the Boston Red Sox: ugly, vitriolic, rotten to the core. Not even a great moment like the standing ovation Fenway Park fans gifted Kevin Youkilis following the last at-bat of his Red Sox career could mop away the feeling that it didn't have to be this way.

Only maybe a new line of thinking is necessary. Maybe it does have to be this way. The reason Boston is the greatest place in the world to play and the worst place in the world to play is that there is no gray with the Red Sox. They are the best or the worst, playing like the '27 Yankees or the '03 Tigers, with the most brilliant manager or the most incompetent. And for someone like Youkilis, who has spent his entire career with the organization, such certitudes breed deep emotions.

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Kevin Youkilis tripled before leaving his final game with the Red Sox. (AP)

Pour that into a carafe and add a few dashes of ego and pride, and it's a cocktail more Molotov than palatable. Even if Red Sox manager Bobby Valentine had handled Youkilis' situation with care – and he didn't, not in the beginning, middle or end – there was a simple truth preventing an amicable parting: Boston is an impossible place to leave without feelings intervening.

Never mind Jim Rice, Mo Vaughn, Nomar Garciaparra, Manny Ramirez, all iconic and all soured upon their exit. Even Jason Bay, mild-mannered, eminently likeable and a Red Sox star for less than two years, decamped to New York lamenting Boston's offer to him. It could've been sour grapes, sure, or that knowledge playing for the Red Sox can be like a drug, heights unmatched.

It should be the same in New York, too, and sometimes it is. Because the Yankees are seen as this mega-entity, far more corporate than the Red Sox, divorces are accepted as the cost of doing business. Boston still hasn't reached that point, and almost surely it never will.

Because no matter how hard the Red Sox try to do right by their players – and shipping out Youkilis, who was about to fester on the bench, was not just an understandable baseball move but a merciful one personally – this is unavoidable. The Red Sox are Liz Taylor. They marry, they love hard, they fight, they divorce. Baseball's version of Who's Afraid of Virginia Woolf? The answer, after Sunday, is …

1. Kevin Youkilis, the newly minted third baseman of the Chicago White Sox and the first player to switch teams in what many executives believe will be a more interesting trade season than usual, what with the extra playoff slot emboldening teams that may not otherwise have considered pursuing upgrades.

Before the talk turns to others who may or may not be available, the case of Youkilis is an interesting one. He is 33, injury prone and looks old. Certainly changes of scenery are known to revitalize players. Youkilis' issues may go beyond whatever mental boost losing the melanin in his Sox may provide.

[Related: Red Sox get Lillibridge and Stewart from White Sox in deal]

He has swung and missed at a higher percentage of fastballs this year than ever in his career. His struggles against right-handed pitching are palpable. He is hitting ground balls more than 50 percent of the time, a troublesome number for a player whose speed would be described generously as harried slug.

That, too, covers the urgency with which the Philadelphia Phillies are going to make a decision on …

2. Cole Hamels and his future with the ballclub. At this point, it's almost a certainty Hamels is going to free agency. He wants CC Sabathia money. The Phillies are buried underneath the weight of $105 million owed to Ryan Howard, $87.5 million to Cliff Lee, $39 million to Jonathan Papelbon, $22 million to Jimmy Rollins, $20 million to Roy Halladay and $15.28 million to Chase Utley. That's almost $290 million owed to players all 31 and older.

Compound that with other business – potential contract extensions for Hunter Pence and Carlos Ruiz, the status of free-agent-to-be Shane Victorino – and Hamels' desire for what could be the richest pitching contract ever puts the Phillies in an awkward position, one made more awkward by their mediocrity. Philadelphia is 34-39 and in last place in the NL East. Their farm system, ravaged by trades, is rather bereft. And their team, ravaged by injuries, may not heal in time to give GM Ruben Amaro enough reason to avoid trading Hamels.

[Related: Cliff Lee again denied first win as Rays sweep doubleheader]

Utley could be back this week. Halladay probably will return late July. Nobody knows on Howard. That points more and more to Hamels' availability, a potentially massive addition for contenders and just one of a number of wave-making deadline pitchers. His right-handed counterpart among the highest-impact ones is …

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Zack Greinke (Getty)

3. Zack Greinke, whose Milwaukee Brewers have drifted six games under .500 and sit behind three teams in the NL Central. Greinke has done his part: a team-leading eight wins, 2.81 ERA, 99 strikeouts and just 21 walks over 96 innings. Brewers reliever Jose Veras has issued 22 free passes in 32 innings and closer John Axford 18 in 28⅓.

Like Hamels, Greinke discussed a contract extension before the season. At this point, though, the chances of a deal are about nil. With 18 starts until free agency, why would he accept what's sure to be a below-market offer? No player who values free agency, which Greinke undoubtedly does, would even listen.

GM Doug Melvin is in a unique position. He could set the market with Greinke, like he did trading for CC Sabathia the first week of July 2008. Or he could wait, let it breathe, and cause teams who need that extra push to clamor with a deadline approaching. It's what makes this time of year so fascinating, and it colors the unique case of …

4. Matt Garza and the Chicago Cubs. The Cubs are dreadful. They need success in the draft, in the international market (Jorge Soler for $30 million, for example), in free agency. And perhaps in Garza's case – and almost certainly in Ryan Dempster's – in trades.

While dumping Dempster won't be nearly as bountiful as it would've a week ago – a disabled-list stint with shoulder problems tends to eviscerate a player's trade value – Garza remains a great option because of his control. Not with the baseball, either. He's under contract next season, and even if arbitration is likely to take his salary well past $12 million, it's for only a season, and teams never balk at one-year commitments.

The Cubs have said they're interested in locking up Garza, though his stuff always has played better than his results. Garza sports a below-league-average 4.07 ERA this year. His career adjusted ERA is only 8 percent better than the league. A downswing in home runs allowed last year looks more anomalous, as Garza has allowed 11 in 77⅓ innings this year.

Thing is, he throws 93 mph, mixes up four pitches and doesn't walk many batters. No matter the sketchy results, contenders will flock. The price will be high – perhaps higher than Hamels or Greinke and certainly more than …

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Brandon McCarthy

5. Brandon McCarthy, whose follow-up to a breakout year keeps getting waylaid by the injury scourge it looked like he'd beaten. McCarthy's right shoulder simply won't cooperate with a story that should be among baseball's best.

The 28-year-old discovered statistics, a sinker and a savior in the A's, who wanted him when so many others in the game pegged him a bust. He rewarded them with a 3.32 ERA. This year he's been even better: a 2.54 ERA over a dozen starts in which he averaged more than six innings.

[Related: Rookie's first major-league homer gives A's walkoff win over Giants]

He was great trade bait. He would get to pitch for a contender, in all likelihood, as free agency beckoned. Only his shoulder intervened, and rather than start the finale of the Bay Area's interleague series Sunday, he went to the DL, his trade value in jeopardy, his free agency hampered, his season changed. It's a cruel game, the baseball gods never cease to remind. Sometimes those gifted with 6-foot-7 frames and long levers and what looks like a perfect pitching body break down, while those like …

6. Wandy Rodriguez, a squat 5-foot-10, turn into workhorses. Rodriguez is on pace for his fourth straight season of more than 190 innings, and still, executives seem to come up with a list of reasons why they don't want him. Among those uttered this week:

"He's a National League pitcher."
"Stuff's not good enough."
"Contract."

They're excuses, all of them, because here are the facts: If a player with Rodriguez's track record hit free agency, he would receive a far bigger contract than the $13 million he's owed for next season (with a 2014 option at the same price and a $2.5 million buyout).

So, no, of course Astros GM Jeff Luhnow isn't going to give Rodriguez away when Houston opens for business. Even if his strikeout rate is down, so are his walks, and for a team with a decent-sized ballpark, his stuff could play even better. He should go, as should …

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Jonathan Broxton

7. Jonathan Broxton when Kansas City assesses the relief market and realizes there's not a whole lot of top-end pitchers available. Broxton is not the same pitcher he was when he was dominating in Los Angeles. Not close. His fastball is down 3 mph from its peak. He doesn't strike guys out with ease.

But he knows the ninth inning and doesn't cower from it, and whether it's Boston, Detroit, St. Louis or other teams who could use late-inning relief help, Broxton won't be expensive and will be available, unless Kansas City focuses more on being six games back in the AL Central instead of its minus-42 run differential, which speaks to its true place in the race.

Granted, they're not in the doldrums with …

8. Carlos Quentin and the San Diego Padres, who are fighting the Cubs for the worst record in baseball. Quentin's trade case remains among the more fascinating. Even after going hitless in his last 13 at-bats, he sports a .324/.446/.676 slash line, and as a soon-to-be free agent, his cost won't be terribly prohibitive.

The Padres have an interesting decision with Quentin. New ownership, which is expected to be announced any day, could try to keep the hometown boy. The Padres could ship him out. Or they could hold onto him, hand him a $12 million tender and receive a draft-compensation pick in return if he doesn't accept the offer and signs elsewhere.

The new rules offer a fascinating dynamic: lots of options and even more possibilities of second-guessing. Like, why this offseason wasn't …

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Justin Upton (Getty)

9. Justin Upton traded by the Arizona Diamondbacks? GM Kevin Towers entertained offers. He considered them. He didn't pull the trigger. It was actually a stroke of brilliance from Towers, who understands the value of young, under-control budding superstars. It would be silly not to at least consider dealing him.

Upton's struggles have been evident, though they might be abating. He has multiple hits in seven of his last 11 games, plus a pair of home runs and nine RBIs over the last four days. Nonetheless, his slugging percentage remains below .400.

So what if Towers put Upton on the market again? In all likelihood, the desire for him would be just as robust. Here's the thing: It's not like he's an Alex Rios, a sunk cost. Upton is under contract for a reasonable number (three more years at $38.5 million) and is still 24 years old.

This was a more reasonable scenario before the Dodgers' struggles and Arizona's recent surge – four straight wins, with uberprospect Trevor Bauer ready to debut Thursday – but Towers is a gunslinger, and we can't forget: This is baseball. Odd things happen. Who'd have thought …

10. Kevin Youkilis would turn into a pumpkin only to see Will Middlebrooks take his job? From the Greek God of Walks to the Guy Who Never Walks, change in Boston is afoot.

And for the White Sox, a past-his-prime Youkilis is still an upgrade over the Brent Morel-Orlando Hudson duo of death that had manned third base. If Youkilis finds himself, the White Sox have a $13 million option; if not, the buyout is a reasonable $1 million. To have given up only a utilityman (Brent Lillibridge) and a middling pitcher (Zach Stewart) is a classic Kenny Williams maneuver: high-risk (of breakdown) and -reward (possibly getting the Youk-of-old).

He'll look for more, of course, because when Kenny goes for it, he goes for it. Soon enough we'll see who else is following that course, and who's selling, and who among baseball's most tradeable find themselves in new places.

Different rules. Different contenders. Different agendas. Same baseball, with a June and July that never stops churning.

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