Did Ben Cherington have the worst offseason of all time?

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That question was asked in my chat on Tuesday. Ben Cherington, the Boston Red Sox general manager, threw big money at Hanley Ramirez and Pablo Sandoval, then traded Yoenis Cespedes for Rick Porcello and signed Porcello to a big contract extension. This on the heels of giving Rusney Castillo a $72.5 million deal last summer. The Red Sox committed more than $320 million to those four players, and in 2015 they've been worth a combined minus-2.3 WAR.

That led to Cherington's downfall and Dave Dombrowski getting hired as president of baseball operations on Tuesday, with Cherington eventually getting replaced as GM. Gordon Edes wrote on the impact of Dombrowski's hiring here.

But was it the worst offseason ever for a GM? That's difficult to answer without putting in more hours of research time than I have available. And how do you factor in that a lot people in the game liked Boston's offseason, including the Sandoval contract and the signing of Justin Masterson? Plus, it's not like Cherington destroyed a good team; the Red Sox are actually on pace to win two more games than they did in 2014.

So it's probably not the worst offseason ever.

But I do have a nomination.

Frank Lane was general manager of the Cleveland Indians in 1960. The team had been a powerhouse for most of the late 1940s and 1950s, although it finished behind the Yankees most seasons. After going one game under .500 in 1957 and one game over in 1958, the team went 89-65 in 1959, good for second place, five games behind the White Sox. The Indians' position players were slightly younger than league average and the pitching staff was the second-youngest in the AL.

But Lane was apparently intent on shaking up his lineup. Look at his major deals:

1. Traded Minnie Minoso -- the club's best player in 1959 (5.5 WAR) -- to the White Sox for Bubba Phillips, John Romano and Norm Cash. The Indians threw in three other players, but it was basically Minoso for those three.

As it turns out, trading Minoso wasn't a bad idea. He had two more decent seasons left in him at 2.8 and 2.0 WAR before falling off. Romano was a young catcher, Phillips a 32-year-old third baseman/outfielder, and Cash a first baseman with 112 at-bats in the majors. I'm not exactly sure how big a prospect Cash was at the time. He had spent 1955 and 1956 in the Class B Three-I League but had spent all of 1957 in the military and played sparingly at Triple-A (29 games) and for the White Sox in 1958 (eight PAs) and was a bench player for the White Sox in 1959 (130 PAs). I've read that he was a prospect of note, but he had also played very little baseball in three years.

We'll get back to Cash in a second.

2. Traded Gordy Coleman, Cal McLish and Billy Martin to the Reds for Johnny Temple.

Temple was an All-Star second baseman in 1959 but would accumulate minus-0.2 WAR in two seasons with the Indians. McLish and Martin didn't do anything for the Reds, but Coleman was worth 7.3 WAR in his Reds career. So it was a minor win for Cincinnati.

Then came two trades in April, right before the regular season started.

3. Traded Cash to the Tigers for Steve Demeter.

According to Cash's SABR bio, "Detroit General Manager Rick Ferrell was dumbfounded when Frank Lane, his Cleveland counterpart, offered Cash for Demeter, unsure if he meant 'cold cash or Norm Cash.' " Demeter played four games for the Indians. Cash earned 49.5 WAR for the Tigers, becoming one of the top first basemen of the 1960s.

Then five days later ...

4. Traded Rocky Colavito to the Tigers for Harvey Kuenn.

This is one of the most famous trades in baseball history. Colavito had led the AL with 42 home runs in 1959 and was entering his age-26 season. Kuenn was three years older and had led the AL with a .353 average and 42 doubles, although he had hit just nine home runs. The trade wasn't a disaster along the lines of the Cash deal, but Colavito would hit 139 home runs for the Tigers before eventually returning to Cleveland. Kuenn hit .308 in his one season in Cleveland and was then traded to the Giants in a bad deal that yielded little in return.

The Indians would finish 76-78 in 1960 -- Lane made another trade with the Tigers during the season, swapping managers Joe Gordon and Jimmy Dykes (no kidding) -- and Lane resigned as GM in January 1961. The organization spent most of the next 35 years as also-rans in the American League.

You know what though? Lane may not have had the worst offseason of a GM that year. Bill Veeck of the Chicago White Sox, after losing the World Series, was determined to add more offense to his team. In order to pick up some veteran bats, he traded away Cash (49.4 future WAR), Johnny Callison (38.3), Earl Battey (17.5) and Don Mincher (23.0). That's 128.2 worth of WAR. The veterans acquired -- Minoso, Gene Freese and Roy Sievers -- gave the White Sox 14.5 WAR. The White Sox still managed to remain competitive through 1967, but they finished in second place from 1963 to 1965. Cash, Callison, Battey and Mincher might have meant three AL pennants those years.