5 trades the Dodgers regret making under Andrew Friedman

As we get closer and closer to the annual frenzy of the trade deadline, it's always fun (or not ...) going back in the past to look at moves that altered the baseball landscape. The Dodgers have a long list of trades made under Andrew Friedman since 2014, with most of them benefitting the Dodgers with minimal loss. From blockbusters like the Mookie Betts deal, to smaller-scale deals like the trade that sent Chris Taylor to the LA, Friedman's trade history is overall great.

But for every Betts trade, and for every rare find like Chris Taylor, there are always some that don't quite work out as intended. Whether the player acquired doesn't fit the perceived role, or the prospects given up turn into stars later on in their careers, Friedman's trades with the Dodgers are not all flawless.

So before we get to the 2023 deadline, with fans clamoring about the possibility of trading for some big-time pitching, let's take a look at five trades that didn't work out so well for the Dodgers after everything was said and done.

Joey Gallo. That is all

Last year, in the midst of a 111-win season, the Dodgers had a very underwhelming trade deadline. During that trade frenzy, with names like Juan Soto, Josh Bell and Luis Castillo on the move, the Dodgers acquiring Joey Gallo seemingly came out of nowhere. With a very similar hitting profile in 2022 to Cody Bellinger, and well-documented struggles offensively with the Yankees, it was hard to see where Gallo would fit in on the Dodgers.

Gallo ended up playing just 44 games for the Dodgers and he struck out 57 times in 117 at-bats while posting a .671 OPS. While that OPS was better than his mark with the Yanks, that production was not what the Dodgers needed, and was barely better than Bellinger's (.654 OPS) on the season.

Though this hasn't had a major league impact (outside of screwing the Dodgers in the NLDS against the Padres because their bench wasn't adequate), the early returns aren't great, as Clayton Beeter was dealt to New York.

At the time, Beeter was a Double-A pitcher with a high strikeout rate, but he owned a 5.75 ERA for the Tulsa Drillers. He wasn't highly regarded as a prospect, and this deal was viewed as a low-risk, high-reward for both sides. But this year, Beeter has torn up the minors in the Yankees organization, with a 2.08 ERA in 12 Double-A starts on his way to making an appearance in the Futures Game (where Dalton Rushing was the only Dodger present).

Because of how limited Gallo's role was with the Dodgers, and how Beeter has pitched this year, this was an obvious miss at the deadline, but isn't as costly as other trades (unless Beeter somehow makes it onto the Yankees' big league roster and has an impact).

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Jimmy Rollins ... Why?

This one happened a long time ago, and many Dodgers fans might not even remember Jimmy Rollins' time with LA. But, in December of 2014, the Dodgers acquired the then-36-year-old former MVP shortstop from Philadelphia, along with $1 million in cash, in exchange for Tom Windle and Zach Eflin. This ended a 15-year run with Philadelphia for Rollins, and began what was a short, and relatively unsuccessful time with the Dodgers.

In his final four seasons with the Phillies, Rollins stole at least 22 bases every year. But with the Dodgers, his speed did not show up, as he only swiped 12 bags (on 20 attempts) in 2015. And his speed wasn't the only part of his game lacking, as Rollins posted career lows in AVG (.224), OBP (.285), and OPS (.643) while playing 144 games in his lone season with LA. And it turned out dealing Eflin for that wasn't worth it whatsoever.

Eflin was a mainstay in the Phillies' starting rotation from 2018-2022. After a rough debut year and sophomore season, Eflin made 80 starts for the Phillies from 2018-2021, while pitching near or above a league-average level every one of those years. In 2022, he transitioned to a reliever in the middle of the season as the Phillies went on their run to the World Series.

In the 2022 postseason, he had an impact, posting a 3.38 ERA, and holding both the Padres and Astros scoreless across 6.1 innings in the NLCS and World Series. This year, Eflin signed with the Rays, and in 17 starts, holds a 10-4 record with a 3.25 ERA. It's safe to say that the Dodgers could have used Eflin a few times over the years.

Danny Duffy Disaster

This one really deserves its own longer look, or potentially its own category on this list. While the Gallo trade was odd because of a lack of potential fit and lackluster production with the Dodgers, the Danny Duffy trade completely redefines all of that.

Near the 2021 trade deadline, the Dodgers acquired Duffy and cash from the Royals in exchange for a PTBNL, which ended up being RHP Zach Willeman. Before getting to Duffy, it's important to note that Willeman struggled in the Royals organization at both Double- and Triple-A, eventually leading to his release from the team. He then signed a minor-league deal with the Marlins, and is at Double-A right now.

So, how could I rank this as the third-worst trade in the Andrew Friedman era if the player the Dodgers gave up basically nothing? Well, because the Dodgers basically got nothing in return. Actually, worse! The Dodgers had to pay Duffy $5 million of his remaining salary in 2021, only for him to appear in just as many major league games as Willeman did for the Dodgers.

If you don't understand what that means, Duffy never took the mound as a Dodger in 2021. Even after he didn't pitch in 2021, the Dodgers re-signed him for $3 million before the 2022 season. In 2022, he was sent on a rehab assignment in late August, then he made it to Triple-A OKC, but once again failed to make a major league appearance. All things told, the Dodgers gave Duffy $8 million and the Royals a minor-league pitcher for zero total innings pitched. But I'm here to tell you this trade is somehow not the worst of the Friedman era for the Dodgers.

Tony Watson for Oneil Cruz

If the Dodgers had traded any prospects to Pittsburgh who ended up having a solid big league year or two, this trade probably wouldn't be on here. But as all true Dodger fans know, this was one of two times where the Dodgers were a little too quick to part with a prospect in exchange for a rental reliever for a postseason run. Of course, the prospect I'm talking about is Oneil Cruz. He was in the Dodgers' system back in 2017, but LA needed immediate help in the bullpen as they were making a serious push to contend for the World Series.

So, the Dodgers dealt Cruz and another prospect for lefty reliever Tony Watson, who actually was a great pickup at the time, posting a 2.70 ERA in 20 innings, with a 2.25 ERA in 12 postseason innings. He was exactly what the Dodgers were looking for in the bullpen, and even was credited with two wins during the 2017 World Series.

But unfortunately, we now know the Dodgers lost that 2017 World Series to the Astros in seven games, and one half-season of Watson just to get a World Series berth doesn't feel worth what it once did, considering LA's recent run of dominance (two other WS appearances and one title) as well as Cruz's rapid ascent as a prospect.

The massive, slugging shortstop became Pittsburgh's top overall prospect (#22 in MLB) before being called up in 2022. Cruz finished sixth in NL Rookie of the Year voting, despite only playing in 87 games, and this season was off to a decent start before getting injured. Cruz is likely destined for MLB stardom, and the Dodgers would sure love to have a guy like him right about now given the weakness at shortstop.