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Career Profile: Randy Winn

Career Profile: Randy Winn

Randy Winn announced his retirement last week. Here's a Career Profile and an examination of how he developed as a prospect.

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Randy Winn was drafted by the Florida Marlins in the third round in 1995, from Santa Clara University. Fast and quick, he played both baseball and basketball but was considered a better pro prospect on the diamond. He was seen as a future leadoff hitter due to his speed, although questions about his power potential and approach at the plate kept him from the first two rounds. His pro debut was good: .315/.365/.385 in 51 games for Elmira in the New York-Penn League. He stole 19 bases, but didn't show much power and had a below average walk rate. A similar player now would get a Grade C from me, interesting enough to be mentioned, but a cautious grade pending higher-level data.

Moved up to Kane County in the Midwest League in 1996, Winn hit .270/.340/.313 with 30 steals. On the negative side, he showed very little power, still didn't walk much, and was somehow caught stealing 18 times. He was fast and athletic enough to remain interesting, but obviously need a lot of polish as a player, and I would have rated him as a Grade C still.

Winn began 1997 with High-A Brevard County in the Florida State League, hitting .315/.400/.399 in 36 games, with 16 steals. He was showing more punch and his plate discipline took a step forward. Promoted to Double-A in late May, he remained hot with a .292/.371/.424 mark, hitting eight homers and stealing 35 bases. His walk rate passed the 10% BB/PA threshold of acceptableness and he started showing some power, though he was still caught stealing too often (20 times in Double-A). He was named Fastest Baserunner in the Eastern League, but wasn't protected from the expansion draft and was selected by the Rays.

I panned this move in my 1998 book, keeping Winn's rating as a Grade C and writing that I thought he could develop into a "nice reserve" but that he would never hit enough to be a regular.

Winn spent the '98, '99, and '00 bouncing between Triple-A and the majors. He was great in Triple-A (hit .353 in '99, .330 in '00) but in the majors his lack of power and ineffective use of speed on the bases were problems. He stole 41 bases in this period but was caught 28 times. He was just slightly better than a replacement level player at this stage, with a grand total of 1.2 WAR over four seasons. I felt that justified my judgment about him in the '98 book.

In 2002 he broke out with a much better year in 2002, hitting .298/.360/.461 with 14 homers, OPS+120, WAR 4.5. He also improved his stolen base success ratio dramatically at that point, and began playing much better defense. Every aspect of his game improved. This remained true even after he moved on to the Mariners (traded from the Rays for manager Lou Piniella) and Giants: indeed, his best overall season (at least according to WAR) was 2008, when he posted a 5.0 mark (hitting .306/.363/.426, 105 OPS+, 25 steals in 27 attempts, strong defense).

Winn suddenly collapsed with the bat in 2009 (OPS+ dropped to 76) though he remained good with the glove. However, even the good glovework disappeared in '10, ending his career at age 36. Overall, he hit .284/.343/.416 in 1717 games, with an OPS+ of 99, WAR 28.2 Much of his career value ended up being on the defensive end of the ball.

Most Similar Players: Gary Maddox, Mark Kotsay, Darin Erstad, Ken Griffey Senior, Augie Galan, Wally Moses, Shannon Stewart, Curt Flood, Jim Piersall, and Vic Power.

Up until age 28, there was no reason to think that Winn would be anything more than a slightly-better-than-replacement level player, exactly as one would expect from his minor league record. Given what was going on in the early 2000s, the age 28 performance spike gives one pause, but he maintained his gains for several years and all aspects of his game, including baserunning and fielding, improved. It isn't uncommon for a player to have a performance spike at age 27/28, nor is it uncommon for a player to collapse quickly in their mid-30s. He was always a great athlete, and he figured out how to use that athleticism.

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Fun Facts

At Santa Clara University, Winn was roommates and teammates with Steve Nash.

by Kapellmeisters on Apr 6, 2026 2:21 PM EDT reply actions  

no idea

No idea. But there have been guys rated higher, I’m sure.

by John Sickels on Apr 6, 2026 7:01 PM EDT up reply actions  

Just off the top of my head

Ryan Westmoreland was drafted in the fifth round and was given a grade B after his debut season.

by Grudyfan on Apr 7, 2026 8:27 PM EDT up reply actions  

Any prospects nowadays that would be fair comps?

"People don't kill people. Burning oreo packages kill people."

by crolfer on Apr 7, 2026 3:08 AM EDT reply actions  

Xavier Avery?

Not a college guy, but good athleticism and has been gradually improving his plate discipline and power skills as he climbs the rungs of the minors.

by Grudyfan on Apr 7, 2026 11:09 PM EDT up reply actions  

Grade C/4th OF

People get so ticked when they see a prospect they have an interest in get these labels, but sometimes these guys really pan out, don’t they?

by drwmsu1 on Apr 7, 2026 9:38 PM EDT reply actions  

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