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The Tuesday Discussion – The Greatest Left Fielder Ever

February 8, 2022


This week we asked our writers to identify the greatest left fielder of all-time.

Here are their replies:


Paul Semendinger – I want to pick a player other than the one who is the obvious answer. I don’t want to get into a long debate about PEDs and legacies and so much more. I want to just focus on who was the best…

But, unfortunately, when one looks at left field, those other topics come up.

It’s impossible to do this exercise without having the other things come up.

In short, the greatest left fielder of all-time comes down to a debate between three players:

Ted Williams

Rickey Henderson

and Barry Bonds.

Three giants of the game. Who was the best?

(Of note, although people remember him as a right fielder, in his career Babe Ruth actually played left field almost as much: 1,128 games in right field, 1,047 games in left field.)

But here’s our debate today…

Rickey or Ted or Barry Bonds?

By WAR, it’s a slam dunk, Bonds wins hands down: Bonds (162.7), Williams (122.1), Henderson (111.2).

And I could stop there.

And, I guess, I will. It’s Bonds. I wish it were Ted Williams. I loved rooting for Rickey Henderson, but it’s Bonds. It has to be. If we look at the numbers, and that’s what this exercise is (for me), it’s Barry Bonds.

(Coming at 1:00 today is a more detailed article from me comparing these three players…)


Lincoln Mitchell – Ted Williams was one of the greatest hitters ever. He hit over 500 home runs and had a career OPS+ of 191 and 122.1 WAR. He also missed five years of his career, including three in his prime, to military service. If he had played those five full seasons-he played a total of 43 games during the two years he was in Korea, Williams would have had closer to 650 home runs and another 30 WAR or so. Williams was a great hitter, but a very one dimensional player. He did not steal bases and his defense was not strong.

My choice for greatest left fielder of all time won eight Gold Gloves in left field and stole more than 500 bases. For the first decade or so of his career he was an extraordinarily graceful player who could excelled in every aspect of the game-other than pitching. Given how great Williams was why I am I choosing a defensive standout who stole bases as the greatest left fielder ever? The answer, as you can probably guess, is because that player is Barry Bonds who hit a few home runs as well.

Bonds became the face of the PED scandal not so much because he, like so many of the players of his era including so many of the pitchers he batted against, used steroids, but because he was too good on PEDs and he wasn’t nice to the media. However, we know pretty much for sure that Bonds did not use PEDs until 1999 at the earliest and his numbers through 1998, his age 33 season were 99.9 WAR and a 164 OPS+. Ted Williams may have been a better pure hitter, but Bonds was the better overall player.

The PEDs are a concern, but even if Bonds had entered a monastery in 1999, I still might have taken him over Williams. Bonds played the game the way MLB was allowing, perhaps even encouraging in the late 1990s. Moreover, in the mid-1990s when he was not using he was still the best in the game that included many PED users. Lastly, Williams played his whole career in the American League. The AL was much slower to integrate than the NL, so to a great extent he was not playing against the best competition during his big league career.


Cary Greene – Taking everything into account, the answer is Ted Williams

(I have a detailed explanation of my answer coming tomorrow at 10:00 a.m.)


Tim Kabel – It is interesting how many former Red Sox could be on this list. Carl Yastrzemski, Jim Rice, and even Manny Ramirez, if you chose to consider him, would all be among the best leftfielders ever. Rickey Henderson is the only former Yankee who would make the list but, ultimately I would select Ted Williams over Henderson and Stan Musial. Barry Bonds definitely deserves consideration but because of his use of performance-enhancing substances, I would not put him above Ted Williams.


Mike Whiteman – Unlike some weeks where the top player was pretty apparent, things are a bit more interesting in this week’s question.

Here are the top five left fielders per

Barry Bonds Ted Williams Rickey Henderson Carl Yastrzemski Pete Rose

Two of perhaps the most polarizing players of all time in Bonds and Rose. I’m not going to dig into them because neither are my choice.

It comes down to two players for me:

Ted Williams is the most iconic player of the lot. If I had to choose a hitter for one at bat with the winning run on base in the ninth, Teddy Ballgame is my man

Yet, if I’m drafting a player for a team, Rickey Henderson is my choice. We middle-aged Yankee fans got to see Henderson at his peak in the mid-80s. Rickey could beat you in so many ways, especially when he found his power stroke after he joined the Yanks.

The thing that puts Henderson over the top for me in left field is he is perhaps the top “disruptor” in MLB history. Pitchers had to expend considerable energy to keep him off the bases, which was so hard due to his compact batting stance and command of the strike zone. Once he reached base, then the chaos started. Henderson stole second base 1,080 times, and lest a pitcher think once he got to second he could relax, Rickey was a good bet to take third, as he did 322 times. He led the AL in stolen bases eleven of his first twelve seasons. Add solid defense in left (fine in center as well) and some Silver Slugger awards and you get an all around threat.

The fact that he bounced around many teams in his late career make it tempting to downplay his career but make no mistake, he was a legendary, one of a type talent in his prime.


Tamar Chalker – I guess it would have to be between Ted Williams and Barry Bonds. While I hate to give the edge to the Boston player, I think it’s hard to argue against Williams. He’s a Red Sox player I have always greatly respected and I would submit is legendary on a different level than Bonds.


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