Cubs history: How Ken Holtzman helped the Cubs more than three decades after he was drafted

This is a little different trade tracker than the one I posted yesterday.

That’s because it doesn’t begin with a trade. Instead, this trade sequence begins with a Cubs draft pick from the very first amateur draft in 1965.

The Cubs, in general, drafted poorly until Tribune Company took over in the 1980s. Of the Cubs’ first-round June picks from 1965-81 (1981 being the last year under the Wrigley ownership), five never played in the big leagues at all, and most of the rest were bit players. Just one — Joe Carter — had a significant big-league career.

But the Cubs did make a very good selection in the fourth round of the 1965 draft. Ken Holtzman was drafted after his sophomore year at the University of Illinois (you could do that in those days). He was given a $65,000 bonus — that was big money in 1965 — and after 12 starts in rookie ball and the Northwest League, Holtzman came to the big-league Cubs in September 1965.

Talk about something you’d never see now. Holtzman was 19. He barely had professional experience, though he had dominated those 12 starts (1.99 ERA, 114 strikeouts in 86 innings). He held his own for three relief appearances and made the ballclub out of spring training in 1966 and went right to the rotation.

Holtzman was something of a sensation. The Cubs needed something, anything to spark the ballclub. This was the last year of their 20 straight seasons without a winning record, Leo Durocher had just been hired, and Holtzman put up a credible season: 3.79 ERA, 1.187 WHIP, 2.2 bWAR (again, not that anyone knew what bWAR was in 1966).

This article isn’t intended to be a career review for Holtzman, so I’ll just sum up by noting he threw two no-hitters and had several good, but not great, seasons in a Cubs uniform. By 1971 the relationship between Holtzman and Durocher had soured (there was talk that Durocher had made anti-Semitic remarks about Holtzman) and Ken asked to be traded.

GM John Holland granted that request and sent Holtzman to the Athletics for Rick Monday. Holtzman had posted 16.3 bWAR for the Cubs, his most for any team. He went on to have several good years in Oakland and pitched for them in three World Series. In the third one, in 1974, he hit this home run in Game 4:

See the Dodgers left fielder trying to reach over the wall for Holtzman’s homer? That’s Bill Buckner.

Rick Monday, meanwhile, was giving the Cubs five pretty good seasons (11.2 total bWAR) before he was traded, in January 1977, for Buckner and Ivan De Jesus.

That turned out to be a good deal for both teams. Monday played eight years for the Dodgers and famously hit this home run in the 1981 NLCS that beat the Montreal Expos:

There’s another future Cub, Andre Dawson, looking forlornly at Monday’s homer leaving the yard. Monday has been a broadcaster for the Dodgers for more than 30 years since retiring as a player.

Bill Buckner became one of the most popular Cubs of his era. I wrote about him after he passed away earlier this year. Limited in mobility after knee and ankle injuries, he had to play primarily first base for the Cubs, and when Leon Durham moved there in 1984 after the acquisition of Gary Matthews, Buckner was traded to the Red Sox for Dennis Eckersley. Buckner had posted 8.6 bWAR for the Cubs from 1977-84.

The Cubs got 2½ good seasons out of Eckersley — 10.5 bWAR — and this story would have a much better ending if they’d actually done what the A’s did with him after the Cubs traded him for three minor leaguers who never played in the major leagues, moved him to the bullpen. That’s where he solidified his Hall of Fame credentials with five great seasons from 1988-92, including one where he issued just four walks in 73⅓ innings.

It was the other part of the Rick Monday deal that paid off for the Cubs. After Dallas Green took over when Tribune bought the team, he began to make trades to reshape the ballclub, several of them with his former club, the Phillies.

Ivan De Jesus had posted four good years with the Cubs from 1977-80, but his 1981 season was nightmarishly bad: .194/.276/.233 (78-for-403), with -1.3 bWAR. He was just 28, but it was clearly time to move on. Green managed to convince the Phillies to take him in exchange for their 35-year-old veteran shortstop Larry Bowa.

And some minor-league shortstop named Ryne Sandberg.

Now, you have to remember who Sandberg was at the time. He was a 20th-round draft pick who was a decent, but not great, hitter in the Phillies farm system. Green was convinced Sandberg was better than his numbers and got the Phillies to agree to throw him in.

One Hall of Fame career later, the Cubs were still getting production out of drafting Ken Holtzman 32 years after he was selected in that very first amateur draft in 1965. Sandberg had a 68.1 bWAR career for the Cubs.