Sports

10 Jaw-Dropping Trades In Boston Sports History

By Andrew Celani, CBS Boston
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Clockwise from top left: Richard Seymour, Nomar Garciaparra, Kendrick Perkins and Tyler Seguin. (Getty Images)

Clockwise from top left: Richard Seymour, Nomar Garciaparra, Kendrick Perkins and Tyler Seguin. (Getty Images)

BOSTON (CBS) – While the Jon Lester trade to Oakland is still reverberating around the country, especially here in New England, it brought to mind other trades in Boston sports history that were equally as jaw-dropping.

Fans got the sense that Lester would be traded by Thursday’s 4pm deadline no matter what, so the ace leaving town was not shocking in that regard. What was amazing about it though was the return.

Most felt the Red Sox would get back two to three prospects, instead they landed a power hitting right-handed slugger, able to not only blast moonshots over the Green Monster, but play excellent defense in left field as well. Cespedes’ 12 outfield assists are tied for the Major League lead with Sox center fielder Jackie Bradley.

So while we’re on the topic of jaw-dropping trades, here’s the list!

10. Red Sox Trade Jon Lester + Jonny Gomes + Cash To Oakland For Yoenis Cespedes + Draft Pick

(Getty Images)

(Getty Images)

Because this one is most fresh in our mind we’ll start here. For all the reasons I mentioned above, this trade was a true jaw-dropper. Oakland was not even thought to be a consideration. The three supposed frontrunners for Lester were the Pirates, the Cardinals and the Dodgers, then out of nowhere the Athletics sweep in and land the deadline’s biggest piece. This was a deal few saw coming.

9. Randy Moss In 2007

(Photo by Jim Rogash/Getty Images)

(Photo by Jim Rogash/Getty Images)

The Patriots traded a fourth round pick (a fourth round pick!) to Oakland for wide receiver Randy Moss, who after seven Hall of Fame worthy seasons in Minnesota failed to deliver in his two seasons for the Raiders.

His stock was at an all time low, and the Patriots bet on themselves that they could turn Moss’ career around.

Yes, this Randy Moss. And this Randy Moss. This Randy Moss, too.

Moss was reinvigorated in New England and helped Tom Brady set the NFL world on fire in 2007, catching an NFL record 23 touchdowns. Such a turnaround on the field was hardly a surprise, but the fact it only took a fourth round pick to acquire him was surprising, as was his abrupt departure in 2010.

8. Joe Thornton To San Jose

So maybe Joe Thornton wasn't the best captain in the world, and maybe the Bruins needed a roster shakeup to become a contending team. But when Mike O'Connell shipped Thornton to San Jose and got just Wayne Primeau, Marco Sturm and Brad Stuart in return, it was both shocking and embarrassing for the Bruins. (Photo by Mike Stobe/Getty Images)

(Photo by Mike Stobe/Getty Images)

So maybe Joe Thornton wasn’t the best captain in the world, and maybe the Bruins needed a roster shakeup to become a contending team. But when general manager Mike O’Connell shipped Thornton to San Jose and got just Wayne Primeau, Marco Sturm and Brad Stuart in return, it was both shocking and embarrassing for the Bruins.

7. Phil Kessel To Toronto

(Photo by Nick Laham/Getty Images)

(Photo by Nick Laham/Getty Images)

For whatever reason the Bruins of late just don’t seem to have any luck with top-flight, offensive-minded players. The Kessel trade is proof of that, and one of the draft picks acquired in that deal helped land another pure scorer they would eventually part ways with…

6. Tyler Seguin To Dallas

(Photo by Abelimages/Getty Images)

(Photo by Abelimages/Getty Images)

After the Bruins lost in the Stanley Cup final in six games to the Blackhawks in 2013, the team did the unthinkable and traded Tyler Seguin, the team’s high-scoring 21-year-old, to Dallas. Fans still flood the phone lines at 98.5 The Sports Hub in protest every time the topic is brought up.

5. Kendrick Perkins To OKC

(Photo by Brian Babineau/NBAE via Getty Images)

(Photo by Brian Babineau/NBAE via Getty Images)

When the Celtics realized they would be unable to sign Kendrick Perkins at the number they wanted in the summer of 2011, “Perk” and his intimidating scowl were packaged with Nate Robinson to Oklahoma City for Jeff Green, Nenad Krstic and a 2012 first-round pick.

The C’s were banking on the health of big man Shaquille O’Neal for the postseason run, but the big man could barely walk and the team was denied its second NBA title with the Big 3. The promise of Jeff Green still hasn’t materialized, and it’s generally considered the worst trade made under Danny Ainge’s tenure.

4. Richard Seymour To Oakland

(Photo by Al Messerschmidt/Getty Images)

(Photo by Al Messerschmidt/Getty Images)

An integral member of three Super Bowl-winning teams and still just 29 years old at the time, Richard Seymour was shipped out of town one week before the 2009 season began to Oakland. Seymour had held out in the past and, as evidenced by the trade, had fallen out of Bill Belichick’s good graces. The first round pick acquired by the Raiders in exchange for Seymour was used two years later to draft offensive tackle Nate Solder.

3. Kevin Garnett From Minnesota

(Photo by Seve Babineau/NBAE via Getty Images)

(Photo by Seve Babineau/NBAE via Getty Images)

When Danny Ainge traded for Ray Allen on draft night in 2007, Celtics fans had a feeling that something was cooking up. Turns out something was, and a month later the Green traded for 10-time All Star Kevin Garnett in exchange for Al Jefferson, Ryan Gomes, Gerald Green, Theo Ratliff, Sebastian Telfair and two draft picks. The 7-for-1 remains the largest trade for one player in NBA history.

Seven players, many of whom Celtics fans actually liked (particularly Al Jefferson), for the 2004 MVP turned out to be well worth it, as he, Paul Pierce and Ray Allen helped the Celtics win the 2008 NBA Finals the following June.

2. The Dodgers Grant The Red Sox A Do-Over

(Photos by Jim Rogash/Getty Images, Winslow Townson/Getty Images and Elsa/Getty Images)

(Photos by Jim Rogash/Getty Images, Winslow Townson/Getty Images and Elsa/Getty Images)

Otherwise known as the Nick Punto trade, the deal with the Dodgers in late August 2012 hit the restart button for 2013 and helped rid the Red Sox of over a quarter billion dollars in salary for the years ahead.

It was an unprecedented salary dump that few fans had a problem with, but the sheer amount of money freed up was the definition of jaw-dropping.

1. Nomar Garciaparra

(Photo by Jamie Squire/Getty Images)

(Photo by Jamie Squire/Getty Images)

For most of his eight-plus seasons with the Red Sox, Nomar Garciaparra was regarded as a local legend. However, he bought his way out of town by turning down a multi-million dollar extension, claiming the grounds crew at Fenway botched the infield so he’d make more errors and sitting out a crucial game at Yankee Stadium while Derek Jeter was diving into the stands.

The behind-the-scenes stuff was not entirely known to fans, so when Theo Epstein traded Nomar away the faithful were displeased “Nomah” was gone. However that animosity was short lived, because three months later an 86-year-old World Series drought ended.

Honorable Mentions: Babe Ruth traded from Boston to New York for cash, Pedro Martinez traded to Boston from Montreal, Adam Oates traded from Boston to Washington, Ray Bourque traded from Boston to Colorado.

Read more from Andrew Celani by clicking here, or find him on Twitter @ACE_Worldwide.

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