THE Best and Worst Trades of the MLB Offseason

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This winter saw plenty of deals, as teams have continued the trend in recent years of preferring to fill their roster weaknesses via trades verses the more expensive and barren free agent market. In addition, the front office shake-ups in Atlanta, Los Angeles, San Diego, and Tampa Bay helped spur one of the most frenetic Hot Stove seasons in many years. For instance, just this winter we saw Josh Donaldson, Jason Heyward, Justin Upton, Wil Myers, and Ben Zobrist change teams, not to mention other stars such as Yoenis Cespedes, Matt Kemp, Jimmy Rollins, and Jeff Samardzija.

Considering the sheer number of trades made this winter and the collective wisdom in each major league front office, it was extremely difficult to choose deals as the top and bottom moves of the offseason. However, after much soul-searching these are my decisive choices for the Best and Worst Trades made during this past Hot Stove season.

Best

1) New York Yankees acquires SS Didi Gregorius from Arizona in a 3-team trade for RHP Shane Greene.

Perhaps I am higher on him than the consensus or lower on what is considered league-average at shortstop at the major league level, but in Gregorius I see a dynamic defensive shortstop who should draw enough walks and hit enough homers to keep pitchers honest. Gregorius is only 25-years-old and I think the Yankees just found their shortstop for the rest of the decade.

In return they parted with Shane Greene, a 26-year-old righty without dominant stuff or a major pedigree. He posted solid numbers last season in his first experience at the major league level and should settle in as a decent #4/#5 starter. That’s a good piece, no question, but certainly nowhere near as scarce as a league-average (or slightly better) shortstop. The Yankees got a steal in this trade.

2) St. Louis Cardinals acquired OF Jason Heyward and RHP Jordan Walden for RHPs Shelby Miller and Tyrell Jenkins.

This is not necessarily a negative statement about the Braves side of this trade, as they receive 11 years of control of Miller and Jenkins in this deal, two talented pitchers. However, I think this trade allows Heyward to blossom into the top-10 player in baseball type talent he is, away from his hometown and in a new organization. For me, Heyward is my sleeper pick for MVP in the National League, and this deal will look like a flat steal for the Cardinals at the end of the season.

3) Anaheim Angels acquire LHP Andrew Heaney from the Los Angeles Dodgers in exchange for 2B Howie Kendrick.

I am a major Heaney fan, as I have watched him extensively through his amateur and minor league career, and I think he is a solid #3/#4 starter for many seasons. In today’s game, that type of player earns $12-15 million annually and Heaney is under team control for six seasons. In exchange for him the Dodgers receive Kendrick, a terrific player but one under contract for only 1 year at $9.5 million, a solid value. I do not argue Kendrick is a nice get for the Dodgers, but the Angels were wise to acquire this terrific mid-rotation starter for this impending free agent.
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Honorable Mention:  Philadelphia Phillies acquired RHP Ben Lively for OF Marlon Byrd and cash.   Chicago White Sox acquire RHP Jeff Samardzija and RHP Michael Ynoa from Oakland for RHP Chris Bassitt, C Josh Phegley, 1B Rangel Ravelo and SS Marcus Semien.   Toronto Blue Jays acquire 3B Josh Donaldson from Oakland for LHP Sean Nolin, 3B Brett Lawrie, RHP Kendall Graveman and SS Franklin Barreto.

Worst

1) Los Angeles Dodgers traded LHP Andrew Heaney to Anaheim in exchange for 2B Howie Kendrick

The arguments made above still apply, as the Dodgers potentially dealt away 6 years of a 2-4 WAR starting pitcher for one season of a 3-4 WAR player. In the short-term the deal is fine, but this deal will look foolish for the Dodgers in the future.

2) Tampa Bay traded 2B Ben Zobrist and SS Yunel Escobar to Oakland Athletics for CF Boog Powell, SS Daniel Robertson, C John Jaso and cash.

I understand Tampa Bay’s conundrum with Zobrist this winter, as they wanted to trade him before he leaves next winter in free agency – my problem with this deal is trading one of the better middle infield combinations in baseball, signed well under market-rate, for such an underwhelming package in return. Jaso can hit, but the concussion issues will likely force him to play first base or DH, severely weakening the impact of his bat. Furthermore Powell looks more like a 4th outfielder and Robertson projects as a second baseman. Considering how valuable what Tampa Bay parted with, this feels like a woefully light return for Zobrist and Escobar.

3) Miami traded RHP Nathan Eovaldi, 1B Garrett Jones and RHP Domingo German to New York for 3B Martin Prado and RHP David Phelps

This trade falls on this list not because of Prado, as I am captain of his fan club and think he is a terrific, versatile player at second base, third base or left field. And perhaps Phelps blossoms a bit moving to the pitcher-friendly Marlins park and the shift to the National League.

But Eovaldi possesses an elite arm and feels like he is on the verge of a breakout season in 2015. In addition, German has a massive arm and is a sleeper prospect.  For the Marlins to trade four years of Eovaldi for two expensive seasons of Martin Prado, plus including German, makes this a slightly puzzling move for Miami. Miami fans should have preferred them to keep Casey McGehee at third base, have Eovaldi and German remain in the organization and reallocate the financial resources differently.

Honorable Mention:  Oakland Athletics traded SS Yunel Escobar for RHP Tyler Clippard.  Atlanta Braves traded OF Justin Upton and RHP Aaron Northcraft to San Diego for 2B Jace Peterson, LHP Max Fried, 3B Dustin Peterson, and OF Mallex Smith.   Miami Marlins traded LHP Andrew Heaney, RHP Chris Hatcher, 2B Enrique Hernandez, and C Austin Barnes for 2B Dee Gordon, RHP Dan Haren, SS Miguel Rojas and Cash.