I did some analysis over the past 15 years of Twins draft choices that received outsized signing bonus over the past 15 years.
2008 BJ Hermsen 6th round $650,000
2008 Michael Tonkin 30th round $270,000
2009 Steve Liddle 15th $200,000
2010 Dallas Gallant 23rd round $122,500
2010 Kelly Cross 26th round $100,000
2011 Austin Malinowski 16th round $175,000
2011 Trent Higginbotham 26th round $195,000
2012 Zack Larson 20th round $190,000
2018 Laron Smith 25th round $125,000
2019 Edouard Julien 18th round $493,000
Only 2 of those players ever reached the major league level: Michael Tonkin (who is back in the majors with Atlanta after several years of exile) and Julien of course.
The success rate of major league draft picks is marginal at best and most of this money allocated to signing these mostly high school players seems to be money down the drain. The Twins could perhaps adjust their draft strategy to target the higher ranked college bound high school players, The top undrafted player on MLB.com draft prospects was Roch Cholowsky, ranked 44th with a UCLA commitment. Do you utilize a pick of one of the college pitchers they drafted in the 15th - 18th rounds and take a shot at him or a similar prospect?
The Twins went far above draft slot to sign 3rd round pick Brandon Winokur ($1.5 million bonus vs. $859,700 slot value) and a bit over slot to sign Dylan Questad. So they already have significant bonus pool money committed to these two signings.
However, I question the new trend to give out 6 figure signing bonuses to the college players they drafted in the later rounds, including a couple of draft picks who were college seniors like 17th round pick Kade Bragg. Nothing against Kade, but he was a college senior that really had limited leverage in his signing.
In the end, the data suggests that these flyers are probably big wastes of money. The utilization of this money, especially if it is over pool and taxed at 75% is something an organization should do seldom, if at all.