His agent complicates things.
He is a Scott Boras client which traditionally means that he is looking for the largest payout possible. He would also have five years of service time under his belt if negotiations were to take place this offseason. With that in mind let’s examine all short-stops who received contract extensions in the past ten years who had at least five seasons of service time accumulated.
| Date | Player | Team | Position | Years | Total Dollars (millions) | Adjusted Dollars | Service (years) | Agency |
| 10/09/2014 | J.J. Hardy | BAL | SS | 3 | $40M | 42.3 | 9.164 | Landis Baseball Group |
| 11/30/2012 | Alexi Casilla | BAL | SS | 1 | $1.9M | 2.1 | 5.038 | Proformance |
| 04/18/2012 | Erick Aybar | LAA | SS | 4 | $35M | 38.2 | 5.086 | ISE Baseball |
| 07/16/2011 | J.J. Hardy | BAL | SS | 3 | $22.5M | 25.3 | 6.099 | Landis Baseball Group |
| 01/10/2011 | Jason Bartlett | SDG | SS | 2 | $11M | 12.4 | 5.086 | Landis Baseball Group |
| 01/25/2010 | Maicer Izturis | LAA | 2B / SS | 3 | $10M | 11.4 | 5.038 | Legacy Agency |
| 12/16/2009 | Ramon Santiago | DET | SS | 2 | $2.5M | 2.9 | 5.095 | ACES |
| 11/13/2009 | Jack Wilson | SEA | SS | 2 | $10M | 11.7 | 8.147 | Page Odle |
| 07/22/2008 | Cristian Guzman | WAS | SS | 2 | $16M | 18.8 | 9.119 | Stanley King |
Contract data is via MLB Trade Rumors and all adjusted salaries were calculated using this calculator. The first thing that jumps out is that these players are all much worse than Xander Bogaerts. J.J. Hardy’s 8.5 fWAR in the three years prior to his extension is the highest mark of the group and still well short of the 12.7 fWAR Bogaerts achieved between 2015 and 2017. That’s without even accounting for the fact that Hardy was 31-years-old; a decent bit older than the 25-year-old Bogaerts.