Worst Trades in Red Sox History

The Boston Red Sox are one of the game's most storied franchises, but there's an 86-year gap in their championship history that was exacerbated by some bad luck, as well as a few serious gaffes.

While Bostonians wouldn't trade that charming history for anything, at this point, it's still worth noting they would've brought a few more rings into port over the years if they hadn't made these mistakes (skip to the No. 1 spot, Yankee fans!).

5. Sparky Lyle to the Yankees, 1972

Sparky Lyle for Danny Cater haunted the Fenway Faithful during a particularly difficult era of failing to obtain a ring. While the Yankees rode relief ace Lyle to rings in 1977 (he was the Cy Young winner and sixth in the MVP voting) and 1978, Boston was nipping at their heels, unable to get over the hump. Cater's cumulative .262/.301/.384 mark in Boston didn't help much, and he was gone by the end of 1975.

4. Tris Speaker Traded to Indians, 1915

What is it with the Red Sox and trading elite center fielders whenever they get their hands on them? The Sox traded Speaker to the Indians in 1915, and he unleashed 11 years worth of .354/.444/.520 baseball after departing Fenway, entering the Baseball Hall of Fame in its inaugural class. Sure, Boston won two World Series after dealing Speaker, but what was the goal here?

3. Mookie Betts and David Price to the Dodgers, 2020

Is it fair to put this trade on the list, even though Betts and Price haven't played any games that count for the Dodgers, and may never do so? Yes. The motivations were just that rotten. Enough has been written about this trade to fuel a "Liverpool Almost-Champions 2020" parade float for the wealthy Red Sox ownership group. But let's just say that ruining your fans' goodwill by dealing a WAR king like Betts (6.9 in a down 2019 season as a 26-year-old) and an expensive ace in Price (your mistake!) for a damaged package just to save some cash (Alex Verdugo's back didn't even hold up for Spring Training!) was a gaffe, even if the 2020 season is impacted further, saving the Sox some grief.

2. Fred Lynn to the Angels, 1980

When the Red Sox chose to deal Fred Lynn following the 1980 season, he wasn't just Boston's best player. He was the Red Sox. In a controversial move that would be echoed decades later when Mookie Betts went west, Lynn headed to the California Angels in exchange for Frank Tanana, Joe Rudi, and Jim Dorsey. Lynn, the 1975 Rookie of the Year and MVP, was one season removed from a stunning '79 campaign in which he hit .333/.423/.637 with 39 homers and 122 RBI. Like Betts, he slipped a bit the next year (.301/12/61), and hit the road. He was an All-Star the next three years in Cali (though in '81 that selection was on reputation alone), and Tanana (an All-Star on the downswing) and Rudi (a slugger whose best days were long behind him) both struggled in one-season tenures in Beantown.

1. Babe Ruth to the Yankees, 1919

Babe Ruth was sold to the Yankees following the 1919 season for $100,000, in order for Sox owner Harry Frazee to fund a Broadway production called "No, No Nanette." In retrospect, still a really bad idea! Ruth had hit a career-high 29 homers in 1919 for the Sox, and immediately bumped that up to 54 when he hit New York, revitalizing the Yankees' franchise from the ground up immediately. There wouldn't have been a Murderers' Row in the Bronx without this horribly-researched cash grab. 100 years later, the Sox did the modern equivalent of the same move by dealing Mookie Betts for similar motivations. Only time will tell if Betts' absence from a shortened season will have the same seismic effect.