Twins general manager Terry Ryan is a Well-Respected Baseball Man™.

He was drafted by the Twins in 1972 and pitched four seasons in their farm system. From there he became a scout and, eventually, the Twins' scouting director. In the fall of 1994, when two-time World Series-winning general manager Andy MacPhail left the Twins to take the same job with the Cubs, the team chose Ryan as his replacement. He's been the Twins' general manager for 18 total seasons split between two stints, separated by a self-imposed four-season hiatus. Terry Ryan is the Minnesota Twins.

That cliché about someone who has forgotten more about something than most people will ever know is absolutely true of Ryan, a 62-year-old baseball lifer who has earned universal respect from his peers in baseball and from the media covering baseball. All of that is undeniable. However, also undeniable is that Ryan's overall winning percentage as Twins general manager is just .474; the team has won a grand total of one playoff series since 1995. They haven't won a playoff game since 2004, and the Twins have the second-worst record in baseball during Ryan's second stint, with a fifth 90-loss season in the past six years currently looking likely following a disastrous 10-27 start.

When the Twins were winning six AL Central titles in nine years from 2002-2010 they were known for remaining old school as MLB front offices increasingly went new school. Basically they were known for being Terry Ryan, continuing to rely on their scouting chops and well-established organizational approach as waves of analytics and innovation swirled around them. All of that remains true now, except the Twins have fallen even further behind in the various new-school categories while failing to dominate on the old-school side like they used to. In short, it's not obvious what they're even good at relative to the other 29 teams anymore.

It's been quite a while since Ryan's actual moves and the Twins' actual record matched his sterling reputation. There aren't many teams that would stick with a GM for two decades of .474 baseball and zero playoff success. There aren't many markets in which that GM and his longtime front office assistants would receive little criticism and tons of praise for producing 11 losing seasons in 18 years. But the Twins and Minnesota are that rare combination, which is why this preamble seems somehow necessary just to get to a point where it feels comfortable to say … well, it's no longer clear that Terry Ryan should be the Twins' general manager.

Ryan is extraordinarily conservative, which has shown itself in his aversion to spending big money on outside free agents and in several seasons deciding to flat-out leave $10 million or more in projected, ownership-approved payroll unspent. He's targeted mid-level, low-upside veterans in free agency rather than going after bigger fish, most recently spending $200 million on the meh-worthy pitching quintet of Ricky Nolasco, Ervin Santana, Phil Hughes, Mike Pelfrey, and Kevin Correia. Those five free agent additions have combined to give the Twins a 4.60 ERA in 1,435 innings; three of the contracts stretch beyond this season.

Ryan's conservative nature is also apparent from his repeated moves during both GM stints to over-commit to current, mediocre Twins players with misguided contract extensions and re-signings. For instance, Pelfrey posted a 5.19 ERA with just 101 strikeouts in 153 laborious innings on a one-year deal with the Twins in 2013 and was re-signed to a two-year deal (he had a 4.73 ERA in those two years). Even when Ryan has gotten good value from low-cost, short-term free agent pickups he has erased those gains by signing those same players to multi-year extensions well beyond their usefulness.

Ryan signed Kurt Suzuki to a one-year, $3 million deal in December of 2013. Suzuki was an overworked 30-year-old catcher coming off a four-season stretch in which he hit .237/.294/.357 with poor defensive numbers, but he put together a good first half for the Twins. Rather than trading Suzuki in what would be a 92-loss season, the Twins signed him to a two-year, $12 million extension on the day of the trade deadline. Suzuki has hit .237/.290/.320 with poor defensive numbers in 181 games since signing the extension. He's essentially been a replacement-level player for all but four months of the past seven seasons, but the fourth of those four months is when Ryan gave him a multi-year extension.

Hughes' story is similar, but even more costly. Signed by Ryan to a three-year, $24 million deal in December of 2013, the former Yankees top prospect turned into a strike-throwing machine in Minnesota and had a career-year while posting the best strikeout-to-walk ratio in modern baseball history. It was a remarkable transformation by a 28-year-old with a lifetime 4.53 ERA. Rather than riding out the rest of the contract and getting Hughes for two more years at $8 million per season Ryan handed him a three-year, $42 million extension. Hughes has a 4.79 ERA in 192 innings since signing the extension, which doesn't even begin until 2017.

What the Twins are left with is a mid-level payroll in the $110 million range, $60 million of which is devoted to Nolasco, Santana, Hughes, Suzuki, Glen Perkins, Tommy Milone, and Kevin Jepsen. Ryan has always been risk-averse, but of late his risk-aversion has turned into upside-aversion masked as making so-called "safe" bets on veterans. Those bets include owing $40 million to the Santana-Hughes-Nolasco trio next season, leaving little wiggle room to upgrade a pitching staff that has ranked 14th, 10th, 15th, 14th, 13th, and 13th in the 15-team American League since 2011 while producing by far the fewest strikeouts in baseball.

When they were winning under Ryan the Twins were simply better than most teams at scouting and player development, which was crucial because they were never going to outspend or innovate more or take more risk risks. They were a tight poker player folding unless they had a great starting hand (Joe Mauer, Johan Santana, Justin Morneau, Francisco Liriano, Torii Hunter) and then playing them by the book in the hopes of walking away from the table with a small profit. Of late those great starting hands have disappeared and when the Twins have attempted to loosen up their approach via free agency they've failed miserably. Or, put another way, an awful lot of lemons have been coming off the assembly line at the Twins' player development factory, laying bare the organization's inability to adjust without collapsing.

Matt Garza is the only Twins first-round draft pick since 2003 to produce 10 or more wins above replacement as a major leaguer, and they traded him away at age 23. Trevor Plouffe is the best first-round pick during that time who actually stayed with the Twins, and he's a third baseman with a .246/.308/.421 career line. Plouffe and Brian Dozier count as the established position player development success stories in Minnesota these days, and the biggest standout on the pitching side is Kyle Gibson and his 4.50 career ERA. Once the prospect well ran dry the thirst made the Twins do some things they'd rather forget.

Ryan stepped down as GM following the 2007 season, citing burnout after the team dropped from 96 to 79 wins. His promoted-from-within replacement, Bill Smith, proved totally overmatched and made a series of poor decisions that set the team back. Smith traded Johan Santana for a four-prospect package that provided almost zero value to the Twins, later compounding his mistake by giving up on Carlos Gomez at age 23. He also traded the aforementioned Garza and starting shortstop Jason Bartlett for future bust Delmon Young—a trade that essentially built the Rays' eight-year run of success—and swapped top catching prospect Wilson Ramos for "proven closer" Matt Capps. Big moves, big failures. And please never mention the name "Nishioka" to a Twins fan.

Because of the damage done during the brief but disastrous Smith regime, some Minnesotans feel that Ryan should be given an especially long leash for getting the team back on track. There's no doubt at least some truth to that, but Ryan also hand-picked Smith as his successor and stepped down at a time when the Twins had several huge decisions—including trading away a 28-year-old two-time Cy Young winner—to be made. Smith made them and made them badly, but to act as if Ryan was a non-entity during that time or not responsible for the mess he left on his old desk for Smith seems disingenuous.

Ryan held the GM job from 1995-2007, stepped down while handing the keys to his preferred replacement, and remained involved with the team before re-taking the GM job in 2012. He neither left a clean slate for Smith nor was he left a clean slate by Smith. His second stint as GM has been littered with questionable decision-making, bad free agent spending, the inability to develop pitchers, and an overall sense that the Twins are lagging behind most teams in lots of key areas on and off the field. Or as Twins owner Jim Pohlad phrased it earlier this month in assessing the damage: "Total system failure." Ultimately, though, it can also be objectively boiled down to this: Terry Ryan is the Twins and the Twins have been very bad for six years and a below-.500 team with zero postseason success for 20 years.

Amid all the losing the Twins have assembled a highly rated farm system. The young core—first-round picks Byron Buxton and Jose Berrios, plus Smith-signed international prospects Miguel Sano and Max Kepler—is one they can potentially build around. This is a team on the rise, albeit with a massive step backward taking place this season. The question is not whether a Ryan-led organization can successfully rebuild and return to contender status within the next 2-3 years, but rather whether Twins fans should want Ryan and his right-hand men leading the organization when that happens. It's increasingly difficult to make a compelling case for him keeping the job without pointing to positive things that happened a decade (and a whole lot of losing) ago.

Terry Ryan is a Well-Respected Baseball Man™, but when does that cease being enough?