Joel Sherman

Joel Sherman

MLB

Five takeaways from the wildest trade deadline day ever

Among baseball’s unwritten rules is that at this time of year sellers send veterans to buyers, who respond by sending back prospects. Rinse, repeat.

The understanding was that contenders do not trade critical players off their 25-man roster — that has been viewed in the past as self-defeating. Why give up key players to get key players?

But that unwritten rule went the way of the traditional doubleheader Thursday. In arguably the wildest, most impactful trade deadline in history, what stood out was not only that two of the majors’ best starters — Jon Lester and David Price — were moved, but that significant major leaguers were dealt to make it happen.

The Red Sox got back Oakland’s cleanup hitter, Yoenis Cespedes, as part of the Lester transaction. The Tigers surrendered Austin Jackson to Seattle and Drew Smyly to the Rays in order to get Price in a three-team maneuver. A year ago, Allen Craig and Joe Kelly were keys to the NL champion Cardinals who played the Red Sox in the World Series. On Thursday, they were swapped to Boston for John Lackey. Even the Yankees’ acquisition of Stephen Drew entailed Kelly Johnson going to the Red Sox.

This was all a result of teams getting more creative and bolder. If prospects are overvalued in this market, then proactive organizations will figure a way around this. It also was about the Red Sox, who were not trading to rebuild as much as to position themselves to be contenders again in 2015.

The Red Sox system is loaded for a potential run at Marlins slugger Giancarlo Stanton.AP

Cespedes, Craig and Kelly all figure to be part of that effort immediately. The Red Sox also got a competitive balance draft pick (between the first and second rounds next year) and three pretty good prospects for Jake Peavy and Andrew Miller. That deepened an already stocked farm system, which gives Boston both low-pay choices and high-end trade fodder should someone such as Giancarlo Stanton ever come on the market.

That was my main thought on this momentous deadline day. Here is the rest of my top five:

2. Every year, I hear the Tigers do not have a strong farm system. Yet every season general manager Dave Dombrowski finds a way to get what he wants. He combines boldness, self-assurance and craftiness better than anyone else. The A’s were the talk of this trading July with the acquisitions of Jeff Samardzija and then Lester.

After losing to Detroit in back-to-back postseasons, Oakland was in a bit of a July victory lap. Then the Tigers got Price to unite with Max Scherzer and Justin Verlander — the last three AL Cy Young winners — plus Anibal Sanchez (a previous July Dombrowski add) and Rick Porcello after Detroit obtained Joakim Soria to try to deal with the late-inning problems. The Tigers are not perfect — they are weaker in center without Jackson, for example — but boy would they be tough to beat in an October series.

3. With that said, hat tip to Oakland general manager Billy Beane. In 26 days, he was willing to trade his best prospect (Addison Russell), his 2013 first-round pick (Billy McKinney) and his cleanup hitter (Cespedes) to get Samardzija and Lester and further verify he is tired of the rep of not being able to win in the playoffs and is totally going for it.

Remember, 40 percent of the expected rotation — projected Opening Day starter Jarrod Parker and A.J. Griffin — needed Tommy John surgery and never threw a pitch this year. Oakland didn’t relent. Lester’s bulldog history and postseason cred helps a rotation where the endurance of Sonny Gray and Scott Kazmir are in question, and Samardzija has yet to prove himself in October.

4. You know what is funny when you think about it now: That last offseason began with the Yankees trying to get under the $189 million luxury-tax threshold. This month, they used their willingness to add salaries to obtain Brandon McCarthy, Chase Headley, Martin Prado and Drew.

The Yankees were able to absorb Martin Prado’s salary from the Diamondbacks.Getty Images

The Yankees hope that incremental improvements and versatility help them find enough wins to get in the playoffs. Drew has played nowhere but shortstop, but the Yanks will play him at second and think he also can man third. Headley can play both infield and outfield corners. Prado can play second, third and left field and probably will see a bunch of time in right.

For the future, Prado (signed through 2016) is Alex Rodriguez insurance. (Did you think we would really get through this without mentioning him?)

But really this is an audition for Headley and Drew, too, both free agents after this season. It wouldn’t surprise me if you saw a Drew-Prado double-play combo for 10 games as an experiment for a post-Derek Jeter world. In that scenario, Headley could be retained as the A-Rod (him again) insurance plus a safety net at first, left and right.

The Yanks offered Drew a two-year contract last offseason to play third base in 2014 and replace Jeter in ’15. So they already have considered him as the heir.

5. It is always hard to define winners and losers on deadline day. Consider that Josh Donaldson was barely mentioned as part of a deadline 2008 deal, the same for Corey Kluber in 2010. Both are stars now. So who knows?

But it does feel as if the Phillies needed to move some veterans and salaries. General manager Ruben Amaro stated he was not offered enough to deal anyone. But 29 other clubs are in unison telling Philly there is nothing worse to have in the sport than fading, older, expensive players with bad triggering options, and that is pretty much the Phillies roster. You don’t get good returns for them. You just try to move on as best as possible.

Thus, the Phillies were losers. Meanwhile, Kansas City (1985) and Toronto (1993) have gone the longest without making the playoffs. Both need sprucing. Neither spruced. So they, too, were losers.

The Orioles did not upgrade as much as the other AL division leaders — Detroit and Oakland — but Miller is an overpowering lefty reliever put in the hands of Buck Showalter, one of the best bullpen orchestrators in the sport. So they won. Turning a waive-wire pickup like Sam Fuld into a potential mid-rotation starter like Tommy Milone from Oakland made the Twins winners. And by getting a good lefty reliever (James Russell) and a versatile speedster (Emilio Bonifacio), the Braves also upgraded for the stretch run.