After the 1918 pennant, the Cubs flailed around for a few years. They had some winning seasons in the early 1920s, but never came closer than 12 games out of first place. The 1926 season represented a major improvement over 1925, and then in ‘27 the Cubs looked like they were going to break through. From June 29 through Aug. 16 they went 31-13 and were in first place by six games.

A 16-28 collapse killed the idea of a pennant, though, and that might have led the Cubs to make the deal they made in the offseason.

June 7: Acquired Hal Carlson from the Phillies for Jimmy Cooney and Tony Kaufmann

Cooney had played only a bit over a year with the Cubs, but only a week before this trade he was involved in an unassisted triple play, the only one in Cubs history. Interestingly, Cooney had himself been the victim of such a play two years earlier.

He wasn’t the key to this deal, it was Kaufmann, who had several good years for the Cubs in the mid-1920s. He got off to a bad start in ‘27 so the Cubs wanted a replacement.

In Carlson, what they got was a starter nine years older than Kaufmann. The Cubs were in “win-now” mode, though no one called it that back then, so at the time Carlson was seen as the safer bet.

Carlson actually had a good year for the Cubs at age 35, going 12-8 with a 3.17 ERA and 15 complete games in 22 starts (27 total games). That was worth 3.3 bWAR. He stuck with the Cubs through 1930, though was never that good again, although he did pitch in two games of the 1929 World Series.

Kaufmann pitched in only five games for the Phillies. It was later reported he’d had an elbow injury. Eventually he wound up with the Cardinals on waivers before the ‘27 season ended, but only pitched off and on for them for a few years, the injury was too much. Cooney was out of the major leagues after a year with the Braves in 1928.

So the Cubs got Kaufmann’s best years, then traded him for a useful (if older) pitcher.

This was a win for the Cubs.

June 9: Acquired Eddie Pick from Kansas City (American Association) for Howard Freigau, Luther Roy and cash

Again the Cubs go to the independent minor leagues for a player.

Freigau, an infielder, had played well for the Cubs in 1925 and 1926, but got off to a slow start in ‘27. Roy, a righthanded pitcher, posted a 2.29 ERA in 11 relief appearances for the Cubs in ‘27 after they had acquired him from Cleveland the previous offseason.

Pick, a third baseman, had played briefly for the Reds in 1923 and 1924 before putting up good numbers at Kansas City in 1925 and 1926, and for the first couple of months of 1927, batting over .330 and with a SLG over .500 all three years (stats from that time are somewhat incomplete, though clearly Pick had some power).

It didn’t really work out. Pick hit just .171/.254/.254 with two home runs in 54 games for the Cubs before they shipped him to another minor league club after the season.

Neither Freigau nor Roy had much impact in the majors after this deal.

So it didn’t do much other than give the Kansas City team some cash.

July 12: Acquired Fred Haney from the Red Sox for cash considerations

Haney, an infielder, had been a pretty good player for the Tigers and Red Sox from 1922-26, and even in ‘27 his numbers in Boston were decent.

But he played in just four games for the Cubs before they shipped him to a minor league club in Indianapolis (see below).

I mention Haney because he went on to be a major league manager, nine seasons in all, including managing the Milwaukee Braves to both their pennants, in 1957 and 1958. He resigned after losing a pennant playoff in 1959, but was contacted by Gene Autry to become the first general manager of the Angels, and held that job until 1968. Among the young executives who trained under him were Cedric Tallis and Roland Hemond, both of whom went on to become successful GMs.

Quite the career for a man who’s only a footnote in Cubs history — all he did was pinch-hit (0-for-3) and pinch-run (didn’t score a run).

August 9: Acquired Elmer Yoter from Indianapolis (American Association) for Fred Haney and cash

Truth be told, Yoter didn’t do much more than Haney did. He played in 14 games for the Cubs in 1927 and 1928 and batted .222/.323/.333 (6-for-27) with one double and one triple. He did have one big game, going 3-for-5 with three RBI in this 13-1 win over the Phillies.

August 20: Acquired Freddie Maguire from Toledo (American Association) for cash considerations

I mention Maguire, a second baseman, here not so much for his contributions in his one Cubs season, though it was pretty good: .279/.312/.350 with 24 doubles in 140 games in 1928, 2.4 bWAR.

More so, I note him because with a season that good, the Braves thought he was good enough to take in the Rogers Hornsby deal at the end of the ‘28 season.

Spoiler alert: He wasn’t. He had negative bWAR each of his three seasons with the Braves.

But he helped bring Hornsby to Chicago, so that in itself produced value for the Cubs.

September 1: Signed Art Nehf as a free agent

This has to be viewed in the context of its time. Nehf had been a very good pitcher for the Braves and Giants starting in 1915. He’d pitched in four World Series for the Giants but started declining in the middle of the decade and wound up with the Reds, who released him Aug. 30.

Well. As play began Sept. 1, 1927, the Cubs were still in first place, a game ahead of the Pirates. But since their peak Aug. 16, they had lost 10 of 13 and likely were getting a bit desparate.

And there was Nehf, age 35, who had been a World Series pitcher just three years earlier. And it cost them no players to get him, and only a month’s salary.

I guess you could kind of look at it like getting Cole Hamels in 2018.

Getting Hamels didn’t help the Cubs in the 2018 postseason and getting Nehf didn’t get the Cubs to the WS in 1927. They went 12-18 after Sept. 1.

It wasn’t Nehf’s fault, though! He pitched very well for the Cubs down the stretch, posting a 1.27 ERA in eight games (two starts). Then he had a good year for them in 1928, too, going 13-7 with a 2.65 ERA and 3.5 bWAR in 31 games (21 starts), all that at age 35, which was pretty ancient for most MLB players back then. He wasn’t as good in 1929, though he did pitch in two games of the 1929 World Series.

All in all, this was a pickup that was well worth it, even if it didn’t quite do what the Cubs hoped.

November 28: Acquired Kiki Cuyler from the Pirates for Sparky Adams and Pete Scott

This is one of the best trades in Cubs history and it happened because Pirates management was pigheaded about what they perceived to be a bad attitude from Cuyler.

Cuyler had a very good rookie year in Pittsburgh in 1924 and then had a spectacular season in 1925, batting .357/.423/.598 with 26 triples and 41 stolen bases, helping lead the Pirates to the World Series title, and he batted .269/.321/.500 with three doubles and a home run in the WS.

That led to a contract holdout in 1926 — about the only way a player could make more money in those days. Eventually signing, there were bad feelings and then there was some controversy among other players that led to the Pirates finishing third, though Cuyler had another good year.

In ‘27 the Pirates replaced manager Bill McKechnie with Donie Bush, who was reported to want to have a more “disciplined” team. Cuyler got off to a good start, but then this happened, per Cuyler’s SABR biography:

Cuyler was batting. 329 for the first-place Pirates on May 28 when he tore ligaments in his ankle sliding into third. During the weeks after he returned to the lineup on July 9, tensions between the player and his manager flared, resulting in one of the most enduring mysteries in Pirates history. Not only upset that he was moved from center field to right field, Cuyler objected to batting fifth and especially second, instead of his customary third position.

Long story short, that led to more acrimony between player and management and after Cuyler was reported as “failing to slide” on a force play in an August game, he was benched for the rest of the season, including the ‘27 World Series, where the Pirates got swept by the Yankees.

Obviously no team would do anything like that today, but… this was almost a century ago and that’s kind of how player/management relations went at times.

Thus it was kind of necessary for the Pirates to trade Cuyler for whatever they could get. Scott played one year in Pittsburgh and Adams two and neither did anything distinguished there.

Meanwhile, Cuyler had eight fantastic years with the Cubs, batting .325/.391/.485 with 79 home runs and 161 stolen bases. He stole 43 bases in 1929, leading the National League and helping the Cubs to the pennant. It would be 51 years before a Cub would steal that many bases again (Ivan De Jesus, 44 in 1980). Cuyler produced 26.3 bWAR as a Cub and it likely would have been more, but by 1933-34 injuries had taken their toll. He was released midway through 1935, so played in just two World Series for the Cubs.

Cuyler finished with 2,299 hits, 328 stolen bases and a career .321 BA, and was posthumously elected to the Hall of Fame in 1968 (he died young, aged 51, in 1950 of a heart attack). He’s one of the greatest players in Cubs history and should not be forgotten.

Incidentally, if you didn’t already know, his nickname is pronounced “Cuy-Cuy,” a play on the first part of his last name, not “Kee-Kee.” (Cuyler’s actual first name was Hazen.)

These transactions are an A grade due to the acquisition of Cuyler.