Other entries in the Trade Series:

Mike: I’ll Take Manhattan: Baseball’s Most Lopsided Trades

A Quick One (Happy Mike)

I'll Take Manhattan: Baseball's Most Lopsided Trades, Revised Edition

I'll Take Manhattan: Baseball's Most Lopsided Trades, Revised Edition (Cont.)

Lee Even Stevens

Lee Even Stevens, Part II—The Sexy Version

Cain and A-Rod—A Bling-Bling Rivalry

Studes: The Best and Worst Teams of the Trade

Smoltz for Alexander

In this part we will look at the individual transactions between the Yankees and Red Sox to determine which were the most lopsided. But first I want to repeat the balance sheet between the two clubs summed per decade, that was tacked on to the previous entry but got lost in the shuffle:

Decade	# Trans	Pre Career WS	Post Career WS	Pre Year WS	Post Year WS	WSAB Pre Career	WSAB Post Career	WSAB Pre Yr	WSAB Post Yr
1900s	11	-587	-54	-19	-13	-291	-36	-6	-15
1910s	7	-110	51	3	3	13	68	6	6
1920s	11	798	908	11	92	350	628	2	85
1930s	8	3	44	-1	-15	35	75	2	1
1940s	1	-25	-6	0	-5	-1	0	0	0
1950s	4	67	32	2	4	25	7	1	0
1960s	6	-242	0	-2	-5	-55	2	0	0
1970s	1	-58	70	0	14	-11	67	0	13
1980s	1	-140	-12	0	-3	-68	-3	0	-3
1990s	2	103	-25	10	4	45	-10	3	1
2000s	0	0	0	0	0	0	0	0	0
Total	52	-191	1008	4	76	42	798	8	88

You'll notice that overall the Yankees have traded experience (191 Pre Career WS to the Sox) for future production (1008 Post Career WS to the Yankees). That's true in macrocosm (i.e., career stats) and in microcosm, that is within the given season (4 Pre Year WS and 8 WSAB Pre Yr vs. 76 Post Year WS and 88 WSAB Post Yr, all in the Yankees' favor). One other thing is that the Yankees have traded quantity, experienced quantity (42 WSAB Pre Career to the Yankees and 191 Pre Career WS to the Sox). Finally, even though these two teams were extremely active dealing with each other in the first four decades of the century, their proclivity to trade with each other dried up in the Forties, when their rivalry is generally acknowledged to have begun in earnest.

Ok, now here are the most lopsided Yankee-Red Sox transactions (by WSAB Post Career Difference):

#1:

Date: January 3, 1920
Trade: Yankees purchase Babe Ruth from the Red Sox.
Pre Career WS Diff: 180 (favoring NYY)
Post Career WS Diff: 576 (NYY)
Pre Year WS Diff: 0
Post Year WS Diff: 51 (NYY)
WSAB Pre Career Diff: 141 (NYY)
WSAB Post Career Diff: 424 (NYY)
WSAB Pre Yr Diff: 0
WSAB Post Yr Diff: 41(NYY)

Big surprise here. This is the most lopsided transaction of all time.

#2:

Date: May 6, 1930
Trade: Red Sox trade Red Ruffing to Yanks for Cedric "Don't Call Me Fred" Durst and $50 K.
Pre Career WS Diff: 47 (favoring NYY)
Post Career WS Diff: 262 (NYY)
Pre Year WS Diff: 0
Post Year WS Diff: 13 (NYY)
WSAB Pre Career Diff: 28 (NYY)
WSAB Post Career Diff: 174 (NYY)
WSAB Pre Yr Diff: 1 (NYY)
WSAB Post Yr Diff: 9 (NYY)

Another Hall-of-Famer acquired in his prime (age 25). In the Sox's defense Ruffing showed very little of his future success in his six-plus seasons in Boston (only one park-adjusted ERA better than league average and a 39-96 record). Then again, Durst wasn't much of a player and he was 33 with one partial season left in his tank. The Red Sox inserted him in outfield apparently as a starter for the first and last time in his career.

#3:

Date: December 15, 1920
Trade: Red Sox trade Waite Hoyt, Harry Harper, Mike McNally, and Wally Schang to Yankees for Muddy Ruel, Del Pratt, Sammy Vick, and Hank Thormahlen..
Pre Career WS Diff: 29 (favoring Bos)
Post Career WS Diff: 180 (NYY)
Pre Year WS Diff: 0
Post Year WS Diff: 18 (NYY)
WSAB Pre Career Diff: 31 (Bos)
WSAB Post Career Diff: 124 (NYY)
WSAB Pre Yr Diff: 0
WSAB Post Yr Diff: 17 (NYY)

Hoyt was another future Hall of Famer, acquired when he was just 21. Schang, Pratt, and Ruel were also productive players, favoring the Sox slightly in the non-Hoyt side of the trade.

#4:

Date: January 30, 1923
Trade: Red Sox trade Herb Pennock to Yankees for Camp Skinner, Norm McMillan, George Murray, and $50 K.
Pre Career WS Diff: 72 (favoring NYY)
Post Career WS Diff: 129 (NYY)
Pre Year WS Diff: 0
Post Year WS Diff: 8 (NYY)
WSAB Pre Career Diff: 40 (NYY)
WSAB Post Career Diff: 94 (NYY)
WSAB Pre Yr Diff: 0
WSAB Post Yr Diff: 16 (NYY)

Yet another future Hall-of-Famer, Pennock, this time acquired at age 29.

#5:

Date: July 29, 1919
Trade: Red Sox trade Carl Mays to Yankees for Allan Russell, Bob McGraw, and $40 K.
Pre Career WS Diff: 69 (favoring NYY)
Post Career WS Diff: 88 (NYY)
Pre Year WS Diff: 4 (NYY)
Post Year WS Diff: 3 (NYY)
WSAB Pre Career Diff: 66 (NYY)
WSAB Post Career Diff: 77 (NYY)
WSAB Pre Yr Diff: 6 (NYY)
WSAB Post Yr Diff: 1 (NYY)

Mays wasn't a Hall-of-Famer (at least he hasn't been elected yet), but he was close, and he sure looked like one on the Sox. Russell had some success with the Sox and Senators. He actually won more games in 1919 after the trade than Mays (10 to 9).

#6 (tie):

Date: May 12, 1933
Trade: Red Sox purchase Billy Werber from Yankees.
Pre Career WS Diff: 0
Post Career WS Diff: 162 (favoring Bos)
Pre Year WS Diff: 0
Post Year WS Diff: 8 (Bos)
WSAB Pre Career Diff: 0
WSAB Post Career Diff: 67 (Bos)
WSAB Pre Yr Diff: 0
WSAB Post Yr Diff: 0

The Sox finally take one, and it's Billy Werber?!? Werber was a pretty good third baseman for the Sox before the sent him to the A's after three seasons.

#6 (tie):

Date: March 22, 1972
Trade: Red Sox sent Sparky Lyle to Yankees for Danny Cater and a player to be named later (Mario Guerrero sent June 30).
Pre Career WS Diff: 58 (favoring Bos)
Post Career WS Diff: 70 (NYY)
Pre Year WS Diff: 0
Post Year WS Diff: 14 (NYY)
WSAB Pre Career Diff: 11 (Bos)
WSAB Post Career Diff: 67 (NYY)
WSAB Pre Yr Diff: 0
WSAB Post Yr Diff: 13 (NYY)

This is one that people usually point to after Babe Ruth, I guess because it is fairly recent (the Sox fans have forgotten their Werber conquest apparently). Lyle was a good pitcher for the Sox before the trade. He was their relieving ace, pitching 100+ innings in 1969 with a 2.50 ERA. The Sox must have looked at his mediocre 1970 season, his falling innings totals n 1970-71, and his falling strikeout totals in 1971 (only 37 in 52-1/3 innings) and thought that even at 26, his best days were behind him. He had a big first year with the Yankees (career high 35 saves) and pitched a ton of inning effectively for them and the Rangers for about a decade.

Cater was a standard issue corner outfielder-first baseman with a funky batting stance. Though he had batted .300 just once prior to the trade, he did finish in the top 10 in batting in a pitcher's era (including a second-best .290 in 1967, the year Yaz won the batting title with a .301 average). Pat Tabler is his most similar batter, so that should tell you something.

#8:

Date: January 3, 1923
Trade: Red Sox sent George Pipgras and Harvey Hendrick to Yankees for Al DeVormer.
Pre Career WS Diff: 2 (favoring Bos)
Post Career WS Diff: 163 (NYY)
Pre Year WS Diff: 0
Post Year WS Diff: 1 (Bos)
WSAB Pre Career Diff: 0
WSAB Post Career Diff: 61 (NYY)
WSAB Pre Yr Diff: 0
WSAB Post Yr Diff: 0

Pipgras was a 23-year-old prospect that would go on to win 24 games for the Yankees in 1928 and 57 over three years (1928-30). Hendrick, also a rookie, was a corner outfield-first base type who had some offense and very little defense. DeVormer was a 30-year-old backup catcher with just 127 ABs under his belt at the time. He split time behind the plate with Val Picinich in 1923 and then was, other than a cup of joe with the Giants in 1927, was through in the majors.

#9 (tie):

Date: July, 1902
Trade: Boston Somersets purchase Tom Hughes from Baltimore Orioles.
Pre Career WS Diff: 20 (favoring Bos)
Post Career WS Diff: 114 (Bos)
Pre Year WS Diff: 5 (Bos)
Post Year WS Diff: 4 (Bos)
WSAB Pre Career Diff: 10 (Bos)
WSAB Post Career Diff: 59 (Bos)
WSAB Pre Yr Diff: 2 (Bos)
WSAB Post Yr Diff: 1 (Bos)

A second win for Boston and it comes when the Yankees were still in Baltimore.

Hughes won 20 games for Boston in 1903 and then was traded back to the Yankee franchise, now in New York and known as the Highlanders, for Jesse Tannehill, who won 21 and 22 games over the next two years for Boston. Hughes was 7-11 in part of a season with the Yanks and then was sent to Washington for Al Orth who won 27 games for the Highlanders in 1906.

#9 (tie):

Date: July 23, 1922
Trade: Yankees send Lefty O'Doul, Chick Fewster, Elmer Miller, Johnny Mitchell, and $50 K to the Boston Red Sox for Joe Dugan and Elmer (J.) Smith.
Pre Career WS Diff: 76 (favoring NYY)
Post Career WS Diff: 94 (Bos)
Pre Year WS Diff: 9 (NYY)
Post Year WS Diff: 0
WSAB Pre Career Diff: 29 (NYY)
WSAB Post Career Diff: 59 (Bos)
WSAB Pre Yr Diff: 2 (NYY)
WSAB Post Yr Diff: 2 (NYY)

The Yankees give up too much to get two veterans? The trade drew a protest from then contending St. Louis, causing Commissioner Landis to change the rules to bar non-waiver trades after June 15.

O'Doul was still a young pitcher when the Yanks shipped him to the Sox. He would blow his arm out in Boston and then go back to the PCL to turn himself into a very good batting outfielder with the Giants, Phils, and Dodgers. (Also when in San Francisco, remember to visit Lefty O'Doul's pub. I have a menu from there that I kept as a souvenir.) He was the prize of the trade though the Sox didn't directly benefit from it.

Smith stinks up the field in NY (.185 batting average), and survives only one more year with the Yankees (122 OPS+) and two more years in the majors. Dugan was the Yankee third baseman and leadoff hitter for many years. So even when the Red Sox "win" one, they don't benefit from it.

#11:

Date: June 18, 1904
Trade: Boston Pilgrims send Patsy Dougherty to the New York Highlanders for Bob Unglaub.
Pre Career WS Diff: 54 (favoring NYY)
Post Career WS Diff: 86 (NYY)
Pre Year WS Diff: 9 (NYY)
Post Year WS Diff: 15 (NYY)
WSAB Pre Career Diff: 29 (NYY)
WSAB Post Career Diff: 50 (Bos)
WSAB Pre Yr Diff: 4 (NYY)
WSAB Post Yr Diff: 10 (NYY)

This was a trade that was highly criticized in Boston in its day. Some theorized that it was orchestrated to help the Highlanders compete with the Giants.

Dougherty played well for the Yankees until he got into a fistfight with manager Clark Griffith in 1906 and was waived. He then became part of the "Hitless Wonder" White Sox.

Unglaub was a weak-hitting first baseman, who started just one season in Boston. Six games after the trade he was hospitalized for blood poisoning.

Here is the full list of Red Sox-Yankee trades ranked by WSAB after the trade (positive values indicate the transaction favored the Yankees; negatives, the Sox):

Trans #	Pre Career WS	Post Career WS	Pre Year WS	Post Year WS	WSAB Pre Career	WSAB Post Career	WSAB Pre Yr	WSAB Post Yr
19	180	576	0	51	141	424	0	41
30	47	262	0	13	28	174	1	9
20	-29	180	0	18	-31	124	0	17
25	72	129	0	8	40	94	0	16
18	69	88	4	3	66	77	6	1
34	0	-162	0	-8	0	-67	0	0
49	-58	70	0	14	-11	67	0	13
24	-2	163	0	-1	0	61	0	0
2	-20	-114	-5	-4	-10	-59	-2	-1
23	76	-94	9	0	29	-59	2	2
4	54	86	9	15	29	50	4	10
36	-61	-84	0	-9	-18	-33	0	0
7	-61	-66	-10	-11	-24	-31	-5	-6
6	-33	-105	0	-8	-10	-30	0	0
8	-5	82	-9	3	-2	25	-3	-1
37	9	80	0	0	0	23	0	0
22	-1	-51	0	-10	0	-19	0	-4
31	46	-36	3	1	34	-16	2	0
16	-135	-51	0	-16	-40	-15	0	-5
10	14	50	0	10	0	15	0	0
52	103	-25	10	4	29	-10	3	1
17	-1	-47	0	-3	0	-9	0	0
13	-17	3	0	9	-13	9	0	9
42	0	23	0	0	0	7	0	0
3	-113	14	0	-17	-85	-6	0	-17
14	10	59	0	11	0	6	0	1
32	35	-8	-2	-4	28	-3	0	-5
33	-73	-8	-2	-8	-37	-3	-1	-3
50	-140	-12	0	-3	-68	-3	0	-3
28	289	19	0	8	157	2	0	0
46	0	12	0	0	0	2	0	0
21	-54	-26	0	9	-42	1	0	13
1	2	0	1	0	0	0	0	0
5	-188	-1	0	-1	-29	0	0	0
9	-28	0	-5	0	-11	0	0	0
11	-209	0	0	0	-149	0	0	0
12	-36	-1	-1	-1	0	0	0	0
15	0	0	0	0	0	0	0	0
26	112	3	0	3	18	0	0	0
27	146	6	0	3	38	0	0	0
29	9	3	2	3	0	0	0	0
35	0	0	0	0	0	0	0	0
38	-25	-6	0	-5	-1	0	0	0
39	0	0	0	0	0	0	0	0
40	67	7	2	4	25	0	1	0
41	0	2	0	0	0	0	0	0
43	-47	-4	0	-3	-9	0	0	0
44	-195	-8	-2	-2	-83	0	0	0
45	0	0	0	0	6	0	0	0
47	0	0	0	0	31	0	0	0
48	0	0	0	0	0	0	0	0
51	0	0	0	0	16	0	0	0

Next, we'll look at the oddly incestuous relationship between the Yankees and the Kansas City A's in the Fifties and how this affected their trading approach.