Dodgers: Worst trades of the Andrew Friedman era

Andrew Friedman has done a lot of good as the general manager of the Los Angeles Dodgers, but some of his trades have not looked as brilliant in hindsight.

The Los Angeles Dodgers hired Andrew Friedman away from the Tampa Bay Rays and inserted him as their President of Baseball Operations on October 14, 2014. At the time, Friedman was an up-and-coming executive with a penchant for making shrewd roster moves and building a talented prospect pool. Meanwhile, the Dodgers were coming out of a period of spending freely and determined that a change of mindset was needed in their decision-making departments.

It is hard to argue with the results thus far. Since taking over, Friedman’s Dodgers teams have won five-straight division titles (seven overall), won the National League pennant twice, fielded two Rookie of the Year winners and one MVP. All of this has been while paring down payroll and building one of baseball’s best farm systems.

In other words, Friedman has done everything the Dodgers have asked him to do, except delivering a World Series title.

Trophy aside, the Dodgers have built a perennial contender primarily from inside the organization. However, there have been cases where the organization has been forced to step outside and make trades to fill holes that, at the time, were thought to put the team over the top.

For his part, Friedman has lived up to his reputation and been shrewd when it comes to parting with the team’s top prospects to add short-term pieces. That’s allowed the team to hold onto the likes of Walker Buehler, Gavin Lux, Dustin May, Corey Seager, and others that now contribute at the major league level.

That isn’t to say that Friedman hasn’t had a few trades that he’s regretted over his tenure. There are a few that he would surely take back if he knew the result wouldn’t have equaled the cost.

More Articles About Dodgers Trade History:

Dodgers trade Frankie Montas and more for Rich Hill, Josh Reddick

When the Dodgers landed Rich Hill and Josh Reddick from the Oakland Athletics on August 1, 2016, the team was in the midst of the playoff push. The team trailed the San Francisco Giants by two games in the National League West and the rotation was beset by injuries, making the acquisition of a starting pitcher almost essential.

On the surface, the trade looked like a winner for the Dodgers. Hill was 9-3 with a 2.25 ERA, a 2.54 WHIP, and a 10.7 K/9 over his 14 starts for the A’s. Likewise, Reddick had been a solid performer over five seasons in Oakland, slashing .257/.321/.440 and averaging nearly 17 home runs and 60 RBI.

Hill was an immediate contributor to the Dodgers, going 3-2 down the stretch and adding a 1.83 ERA, a 2.07 FIP, and a 10.2 K/9. He would spend three-plus seasons in Dodger blue, compiling a 27-14 mark over 63 appearances (62 starts) and working to a 3.30 ERA, a 3.89 FIP, and a 10.7 K/9.

Reddick, on the other hand, never got off the ground. Brought in to fill the hole left by an injured Andre Ethier, the right-fielder played in 47 games for the Dodgers. However, his contributions were minimal, with Reddick slashing a measly .258/.307/.335 and adding only eight extra-base hits and nine RBI in 155 at-bats for Los Angeles.

The cost to acquire Hill and Reddick was a trio of right-handed prospects; Frankie Montas, Jharel Cotton, and Grant Holmes.

At the time, Holmes was the more heavily regarded prospect, but after missing nearly all of 2018, he slid a bit. However, he’s managed to put some of that status back on after a solid season split between Double and Triple-A in 2019, where Holmes worked to a 3.23 ERA over 23 appearances (17 starts) and an 8.4 K/9 mark.

Jharel Cotton would make his MLB debut in 2016, and looked like a potential steal for the A’s, going 2-0 with a 2.15 ERA and a 7.1 K/9 over 5 late-season starts. However, after a rough 2017 season and the dreaded Tommy John surgery costing him the 2018 season, Cotton found himself on the waiver wire this winter.

The true gem here may have been Frankie Montas. Only a Dodgers for one season, Montas was included in the Hill/Reddick trade to protect other arms like Julio Urias and Jose De Leon. After a rough go in the bullpen in 2017, Montas forced his way into the Oakland rotation in 2018, going 5-4 with a 3.88 ERA, a 3.90 FIP, and a 6.0 K/9 ratio over 13 appearances (11 starts). He would build on that in 2019, with a 9-2 mark, a 2.63 ERA, a 3.00 FIP, and a career-best 9.7 K/9 ratio. A PED suspension cost Montas most of the season, and some legitimacy as to the results he put up.

However, if Montas can put the suspension behind him and show that he can continue to progress without any ill-gotten aids, the 27-year-old may be one arm that the Dodgers will regret letting go.

Dodgers trade Willie Calhoun, others for Yu Darvish

As mentioned above, Andrew Friedman has done a great job of steering trade partners towards less-rated prospects in the system, preserving some of the top talents to contribute to the big league club over the years. However, there was one trade that Friedman was forced to stray from that path and give up one of his best prospects.

That was the July 31, 2017 trade that brought Yu Darvish to the Dodgers.

A two-time All-Star in Texas, Darvish was set to be a free agent after the 2017 season and was easily the top available starter on the market. Los Angeles had a 14-game lead in the NL West and didn’t show any signs of needing a big addition at the deadline. However, Friedman and Farhan Zaidi opted to add Darvish because they thought the club was a World Series contender and needed one more piece to make them the favorite to win it all.

To make a trade happen with Texas, and likely keep Darvish from other contenders, the Dodgers parted ways with then #3 overall prospect Willie Calhoun, as well as pitcher A.J. Alexy and infielder Brendon Davis.

Darvish gave the Dodgers nine starts down the stretch, working to a 4-3 record with a 3.44 ERA, a 3.38 FIP, and an 11.1 K/9 ratio. In particular, his final three starts of the season looked promising, with Darvish going 2-0, surrendering just one earned run and striking out 21 over 19.1 innings of work. He would add two quality starts in the NLDS and NLCS respectively, allowing just two earned runs (both on solo home runs) over his 11.1 innings.

The rest, they say, is written in history.

Darvish would get rocked in two World Series starts, allowing nine hits, two home runs, and eight earned runs (nine total) over just 3.2 combined innings and contributing to the Dodgers’ loss in the 2017 World Series. Of course, that performance comes with two asterisks; one for Darvish purportedly tipping his pitches and the other for the Astros cheating scandal.

The deal hurt all the more for the Dodgers due to the cost to acquire Darvish. While Alexy and Davis are not likely to amount to everyday pieces, Calhoun blossomed in his first extended stay in the big leagues in 2019. Getting ample opportunity starting in mid-May, Calhoun went on to slash .269/.323/.524 with 21 home runs and 48 RBI over 309 at-bats for the Rangers. Now 25-years-old, Calhoun was flagged as a breakout candidate in 2020, before he took a fastball to the face in Spring Training and the season was put on hold due to Coronavirus concerns.

It’s tough to know if Calhoun would have factored into the Dodgers plans currently, with Gavin Lux being a better prospect at second base and the outfield well-manned, but his bat certainly would have played.