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What if the Cubs had drafted Robin Ventura in 1988?

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They had their chance... and passed.

Robin Ventura at third base for Oklahoma State in 1987
Getty Images

After having drafted poorly in general during the Wrigley ownership era, the Cubs rapidly improved amateur scouting and draft results when Dallas Green and Tribune Company took over. Shawon Dunston, their No. 1 pick in 1982, became a long-time MLB regular. Rafael Palmeiro was another successful No. 1 pick, though he was traded and of course was later linked to PED use. Beyond the first round, Green’s scouting department also selected Greg Maddux, Jamie Moyer, Mark Grace, Joe Girardi and other successful big-leaguers.

But they whiffed, big-time, on their No. 1 pick in the 1988 draft. The 1987 Cubs had finished 76-85, half a game worse than the White Sox due to a postponed game not made up. So in June 1988, the Cubs had the ninth overall pick, the Sox the 10th.

Robin Ventura had been the NCAA Player of the Year in 1987 as a sophomore for Oklahoma State. The southern California native hit .428 with 21 home runs in ‘87, then “slumped” to .391 with 26 home runs in ‘88. He was seen as just average defensively at third base, but that lefthanded bat would play in any ballpark.

The Cubs had signed Vance Law as a free agent before the 1988 season to play third base. He was 31 years old, and the Cubs gave him a two-year deal. Ventura could have been the perfect successor.

For some reason, though, the Cubs were fixated on Ty Griffin, a second baseman from Georgia Tech. Griffin was definitely a good pro prospect. He hit .357 with 14 homers and 38 stolen bases and was named the ACC tournament MVP. The Cubs selected him, and Ventura went to the Sox with the next pick.

Now why would they do that? The Cubs had a second baseman, and a great one — All-Star and 1984 MVP Ryne Sandberg. What were they going to do with Griffin? Gordon Goldsberry, the Cubs’ VP of scouting, told the Tribune: “He was the best player available to us. He’s going to be a high-average hitter, and he’s going to hit some home runs. He’s a switch-hitter, which I felt was important. He’s a good defensive player, and he steals bases. He might move Sandberg. He’s that good a prospect, in my opinion.”

Wait, what? They’d move an All-Star to make room for a college kid who had proven nothing? While they were going to have a need at third base within a couple of years when Law’s contract expired?

Sandberg shouldn’t have gone anywhere, and didn’t. Instead, the Cubs brass got the great idea, after signing Griffin following his playing for the US Olympic team in Seoul that fall (Ventura was also a US Olympian), that Griffin should be moved to third base.

This is me smacking my forehead. The Cubs could have had a great college hitter who was already a league-average third baseman, and instead they tried to plug the square peg of Griffin into the round hole...

As you can imagine, it didn’t work. Griffin was horrendous defensively at third base. He made 23 errors in 73 games there in 1989 and 18 more in the system at third in 1990 and at that point, the Cubs threw their hands in the air and moved him to the outfield, after he suffered bursitis in his throwing arm. After moving him back to second base in 1991 (and he wasn’t any good there, either) they traded him to the Reds for someone named Bryant. Too bad it wasn’t an older relative of KB. Instead, that player was a career minor leaguer named Scott Bryant, who played one mediocre year in the Cubs system and then was let go.

Meanwhile, Robin Ventura was the White Sox’ starting third baseman by 1990. As you surely know, he had a fine 16-year career that was interrupted by a serious leg injury in 1997. He had 1,885 hits, 294 home runs (including 18 grand slams, tied for fifth all-time) and posted 56.1 bWAR. The WAR figure is 15th all-time among players who were primarily third basemen. It’s not a slam-dunk, but you can make a borderline Hall of Fame case for Ventura.

Here’s one of his grand slams [VIDEO], a walkoff shot for the White Sox against the Rangers in 1991, after which he got carried off the field by Frank Thomas. If only he had been hitting those at Wrigley Field.

I don’t think it’s too difficult to imagine the Cubs winning some division titles during the 1990s had Ventura been their third baseman. Between 1990 and 2003, when Aramis Ramirez arrived to stabilize that position on the North Side, the following players played at least 100 games at third base for the Cubs: Luis Salazar, Steve Buechele, Leo Gomez, Gary Gaetti, Bill Mueller and Kevin Orie. There are some decent players in that list, though some were Cubs when they were nearly done (Salazar, Gaetti) and none provided the consistency that Ventura would have. He’d have been an excellent lefthanded addition to Mark Grace in those lineups. The Cubs of 1993, 1995 and 1996 would have been pushed closer to being contenders with Ventura, especially in ‘95 when they went down to the final weekend in wild-card contention. The ‘98 Cubs might have been able to win the N.L. Central instead of being a wild-card club; imagine that team with both Ventura and Mike Piazza, who the Cubs could have traded for. If Ventura had stuck around through 2001, that, too, could have been a playoff season.

Griffin never played above Double-A. Currently coaching high school baseball in his hometown of Tampa, he told Baseball America in 2018 he has no regrets about his pro career:

“I get a lot of questions: ‘Do you have any animosity? Do you have any regrets?’ ” Griffin says today. “I don’t have any regrets.

“I had a chance to play in a Little League World Series, to be drafted twice, to be drafted in the first round, go to a unique establishment like Georgia Tech, participate in the business world with a top 10 corporation and now be able to be a coach at the high school level.

“I’ve had everything, and more, that I could ask to get out of baseball.”

As for Ventura, though he never played for the team that should have drafted him, he is indirectly helping the Chicago Cubs to this day. In 2016, David Ross told Mark Gonzales of the Tribune that Ventura was a mentor to him when the two were Dodgers teammates in 2003 and 2004:

Robin Ventura treated David Ross to his first private plane ride and gave him a greater appreciation for tri-tip steak.

But the greatest gifts Ventura provided Ross were how to be a good player and teammate.

“The mentor of all mentors,” Ross said.

“He was the first to show me what it’s like to be a good teammate,” said Ross, who has been admired throughout his 15-year career for his handling of pitching staffs and relationships with teammates. “No matter your status in the game, you treat everyone the same, be humble and support your teammates.”

So that’s good, anyway. More than three decades after the Cubs should have made Robin Ventura their No. 1 draft pick, his influence will be felt when the Cubs get back on the field via his good friend, the new Cubs manager.