Dennis Gilbert Reflects On His Career As Top Agent
Scott Boras may have the most impressive client list of any agent in baseball today, but it wasn’t long ago that he shared that title with Dennis Gilbert. From the early 80s until his retirement in 1999, Gilbert was in charge of negotiations for some of the biggest names in the game, from George Brett to Jose Canseco to Barry Bonds. He built a reputation for getting top dollar for his players and churned out record-smashing deals for his top clients. Ultimately, however, Gilbert sold his powerful Beverly Hills Sports Council at a young age, then got back into the game a couple years later as a special assistant to White Sox chairman Jerry Reinsdorf.
Throughout his career, there’s been one constant for Gilbert: the life insurance business. When a friend of his who worked as a baseball agent passed away unexpectedly, Gilbert took over for some of his clients and quickly built his business from there. Still, he never left the insurance industry and juggled both by surrounding himself with the right people in both worlds. It was an impressive feat, given the amount of attention and hours that being a baseball agent requires.
In 1993, Tom Verducci of Sports Illustrated wrote a tremendous piece comparing Boras and Gilbert when they were both at the top of the business. The consensus from around the game was that the two men achieved their success quite differently. “One guy’s a salesman, and the other’s a warrior,” Reinsdorf told Verducci. “Dennis is smooth. While he’s taking your money, he makes you very happy.”
It may be a cliche, but Gilbert is one of a kind. He still greets people with warmth and a few card tricks, and he tends to make lasting impressions. There was no one in his field in the 1980s or ’90s who had a comparable demeanor, and there’s no one now either, nearly 15 years after he transitioned out of the business.
“I don’t have a ton of interaction with agents on a daily basis, but I don’t think any of them do. My approach was unique and I built some strong relationships during that time,” Gilbert tells MLBTR.
Gilbert had a strong rapport with executives around the league, but he had more than one client who rubbed folks the wrong way. Canseco was viewed as a brash and arrogant; Bonds’ rep was as a standoffish individual who didn’t care for the media. Of course, the stain of steroids didn’t help either player’s image. To hear Gilbert tell it, most people didn’t have a full idea of what either man was about and chose only to zero in on the more odious aspects of their personalities.
“The part of Jose that I know about was when he had money he gave his money to his father, mother, sister, brother and a lot of friends around him and he just took care of a lot of people. He had a very big heart and I think that’s a part that people never saw,” Gilbert says. “Barry did a lot of things under the radar also. Going to children’s hospitals, signing dozens of bats every year and handing them out and doing a lot of things that people weren’t cognizant of. They both had soft sides to them.”
Gilbert’s relationships with certain people in baseball continued even after he sold off the BHSC. He was Mike Piazza’s agent during much of his Dodgers prime, and even though Gilbert was no longer representing the catcher towards the end of his stay there, he was “in the room” around the time when Piazza was traded to the Marlins. Once again, in Gilbert’s mind, public perception didn’t quite match reality. As most Dodgers fans understand it, the new FOX ownership group was reluctant to pay the All-Star catcher fair market value on his next contract, necessitating the trade to Florida. On the contrary, Gilbert says that Rupert Murdoch’s baseball arm did everything it could to make things work.
Today, he’s on call for “anything that Jerry Reinsdorf needs” in his role with the White Sox and says that he’s optimistic that the club will have a quick turnaround after a down 2013. He’s considered team ownership, with exploratory talks to purchase the Rangers and, most recently, the Dodgers. One might think that he’s wistful for his days as one of the very top agents in the game, but that’s not exactly the case. Gilbert says that he enjoyed negotiating the contracts and “the baseball part” but isn’t wild about some of the outside stuff the job also calls for. His future could take him in a number of directions, but it’s safe to say that he won’t be sitting opposite of Reinsdorf at the negotiating table again.
MLBTR Originals
A look back at the original reporting and analysis found on MLBTR this past week as we wind down 2013:
- Zach Links details how agents and front office personnel alike find time to squeeze in some business between opening presents and eating 12 grapes while popping champagne corks to a chorus of Auld Lang Syne.
- With only 15 of MLBTR's 2014 Top 50 Free Agents unsigned, Steve Adams asked our readers to re-rank those still on the market. Just under 74% of those surveyed chose Masahiro Tanaka as the most desirable free agent. Nelson Cruz and Matt Garza were next with approximately 6%.
- Charlie Wilmoth asked MLBTR readers who will sign Tanaka. Nearly 39% of you say the 25-year-old right-hander will be wearing pinstripes.
- Mark Polishuk opines teams not willing to bid on Tanaka for any reason other than they feel he cannot pitch effectively in MLB are being short-sighted.
- Steve asked MLBTR readers to name the best nine-figure free agent contract this offseason. You split your support between Jacoby Ellsbury and Shin-Soo Choo.
- Aaron Steen asked MLBTR readers to voice their opinion on the Rangers' offseason to date. More than 72% of you approve of the moves made by GM Jon Daniels.
- Zach was the first to report five teams are bidding for the services of outfielder Sam Fuld. All five teams have proposed minor leagues deals with an invitation to Spring Training.
- Tim Dierkes was the first to learn reliever Jim Hoey is looking to hook on with a MLB team after spending the bulk of 2013 with the Somerset Patriots of the independent Atlantic League.
- Zach compiled the latest edition of Baseball Blogs Weigh In.
- MLBTR has a roster of regular features. Here's the schedule and a brief synopsis of each.
MLBTR Originals
A look back at the original reporting and analysis found on MLBTR this past week, as we check our list to see who's been naughty or nice in the waning hours before St. Nick's arrival:
- Charlie Wilmoth updated the status of the top ten remaining free agents on MLBTR's 2014 Top 50 Free Agents list (posted prior to Grant Balfour's deal-no deal with the Orioles).
- Tim Dierkes examined the pool of unsigned free agents and noted the limited number of available players who could be considered regulars.
- The agent for Kevin Youkilis confirmed to MLBTR his client's decision to play for the Rakuten Golden Eagles in 2014. Joe Bick of Pro Star Management, Inc. also explained the opportunity to spend a year in Japan was a "life experience that was too good to pass up" for Youkilis and his family.
- Zach Links spoke with Giants Vice President and Assistant General Manager Bobby Evans about the team's offseason.
- Damon Lapa, the agent for Jeff Karstens, told Zach he expects at least a dozen teams to attend the right-hander's workout in mid-to-late January.
- Tim was the first to report Jordany Valdespin switched agencies leaving ACES to join Metis Sports Management.
- MLBTR broke the news of catcher Kyle Skipworth being designated for assignment by the Marlins.
- Agent Burton Rocks told MLBTR he has spoken with four or five teams about an unique proposition involving right-hander Juan Rincon: a minor league contract, ideally with an invitation to Spring Training, with an eye towards mentoring young pitchers and continuing in that role as a scout upon his retirement.
- Steve Adams hosted this week's live chat.
- Zach assembled the best of the baseball blogosphere for you in Baseball Blogs Weigh In.
- There are many ways to enjoy MLB Trade Rumors. Here's a refresher on how to use the apps, features, and functions on MLBTR.
MLBTR Originals
A look back at the original reporting and analysis found on MLBTR, as we went 24 hours during the Winter Meetings this past week:
- Zach Links and Luke Adams anchored our around-the-clock coverage providing a daily recap (Day 1, Day 2, and Day 3) of the hard news and rumors with Tim Dierkes and Jeff Todd reporting live from Orlando. Steve Adams meanwhile covered the Rule 5 Draft.
- In a preview of the Winter Meetings, Jeff predicted the wheeling and dealing could lead to some interesting and opportunistic maneuvers.
- Jeff attended the joint press conference with the GMs involved the three-team Mark Trumbo trade and posted their reactions to the deal.
- Jeff asked MLBTR readers which team benefitted the most from the four trades engineered during the Winter Meetings. More than 32% of you who responded to the survey believe the Angels helped themselves the most with the aforementioned Trumbo deal.
- Tim was first with the details of Roberto Hernandez's contract with the Phillies: a one-year, $4.5MM guarantee with an additional $1.5MM in incentives based on innings pitched. Tim also heard the Cubs had been competitive on Hernandez.
- MLBTR was the first to report 12 teams have expressed interest in right-hander Jason Hammel and all are exploring one-year deals.
- Tim broke the news 10 teams are in pursuit of infielder Justin Turner and that Astros outfielder L.J. Hoes is now being represented by MVP Sports Group.
- Tim heard the Cubs offered Edward Mujica a one-year contract to be their closer before he signed with the Red Sox and 8-10 teams have inquired about right-hander Jerome Williams.
- Marlins GM Michael Hill told Tim the decision to non-tender reliever Ryan Webb was simply a reallocation of the club's financial resources and the team's top priority is acquiring a third baseman.
- Tigers President/CEO/GM Dave Dombrowski told reporters, including MLBTR's Steve Adams, the perception the franchise needs to slash payroll is not true and the signing of Joba Chamberlain is the last move he's looking to make.
- Jeff opines the impetus for the Tigers' roster reshaping can be traced to the suspension of Jhonny Peralta.
- The Mets will receive value in excess of the $20MM they will pay Bartolo Colon over the next two years and were able to negotiate such a reasonable price because of his age and history, according to Tim.
- Tim wonders if the Pirates still have payroll space for A.J. Burnett after signing Edinson Volquez.
- Jeff examined the market for Kendrys Morales (#28 on MLBTR's 2014 Top 50 Free Agents list).
- Jeff suggests the Nationals' trade for Doug Fister looks even better now than it did at first glance.
- Mike Napoli told Zach there were a lot teams interested in his services, but it ultimately came down to his wanting to return to Boston.
- Charlie Wilmoth listed the best remaining first base options available on the trade market and in free agency.
- Former first round draft choice Brian Anderson, whose switch to pitching was derailed by injuries, told MLBTR, "I'd love to get back on the field again."
- MLBTR was the first to learn infielder Adam Kennedy, who didn't play in 2013, is planning a comeback and will work out for teams during the second week of January.
- Zach gathered the best the baseball corner of the web had to offer in Baseball Blogs Weigh In.
MLBTR Originals
A look back at the original reporting and analysis found on MLBTR the past seven days:
- Jeff Todd analyzed how the free agent spending this offseason compares to the previous six years. With the Winter Meetings beginning tomorrow, Jeff notes almost half of MLBTR's 2014 Top 50 Free Agents remain on the open market, which will further increase the overall free agent spending levels.
- MLBTR was the first to learn more than 15 teams have expressed interest in right-handed reliever Andrew Bailey, who was non-tendered Monday.
- Tim Dierkes was the first to report the two-year deal Scott Kazmir signed with the A's did not include any options.
- MLBTR was first with the details of the one-year contract right-hander Fernando Rodriguez signed with the A's to avoid arbitration: $600K plus award bonuses.
- Tim examined the free agent signings of Kazmir and Phil Hughes.
- Tim also weighed in on the moves the Tigers have made to reshape their bullpen.
- Jeff opined the Tigers sold short on Doug Fister by obtaining a collection of relatively non-scarce pieces from the Nationals.
- Scott Feldman spoke with Zach Links about his reasons for signing with the Astros and his optimism for the future of the franchise which has posted baseball's worst record three years running.
- Diamondbacks GM Kevin Towers told Zach the financial flexibility obtained in the three-way trade with the Rays and Reds will be used to add starting rotation and bench depth and to acquire a corner outfield bat.
- With the flurry of free agent signings this week, Jeff updated the status of the players who are tied to draft pick compensation after declining a qualifying offer.
- Tim imagined Luke Gregerson would have fetched more for the Padres than Seth Smith.
- MLBTR has released its 2014 Arbitration Tracker displaying all arbitration eligible players, with fields for team, service time, player and team submissions, the midpoint, and the settlement amount. The 2014 Arbitration Tracker can also be filtered by team, signing status, service time, Super Two status, and whether a hearing occurred.
- MLBTR has a separate tender/non-tender tracker with the results from Monday's non-tender deadline.
- Steve Adams explained how the non-tender system works.
- Charlie Wilmoth profiled John Axford as a non-tender candidate who could obtain a two-year deal on the open market. Axford will now have that opportunity as the Cardinals did indeed non-tender the right-handed reliever.
- Steve hosted the MLBTR live chat this week.
- Zach put together the best of the baseball blogosphere in Baseball Blogs Weigh In.
MLBTR Originals
A look back at the original reporting and analysis found on MLBTR this past week scattered amongst the Thanksgiving leftovers, Black Friday shopping bags, and Cyber Monday ads:
- Tim Dierkes was the first to learn the Twins were close to a major free agent signing, which turned out to be Ricky Nolasco (#20 on MLBTR's 2014 Top 50 Free Agents list).
- Tim suggests the Nolasco deal provides little upside for the Twins, but represents the market rate for mid-to-back-of-the-rotation starters.
- Steve Adams contends it is difficult to properly evaluate the four-year, $53MM contract the Cardinals gave to Jhonny Peralta (#21) because of a disconnect between his market value and the media perception of his worth.
- In the wake of the Peralta signing, Jeff Todd offered a series of proposals to create a more effective system of PED disincentives.
- The signing of setup man Joe Smith (#44) was a questionable allocation of resources for the Angels, according to Tim.
- MLBTR contributor Matt Swartz examined the aribtration cases of a pair of right-handers: Justin Masterson and Homer Bailey.
- Tim reported two teams have requested the medicals on free agent left-handed reliever Tim Byrdak.
- Zach Links revisited some of the major transactions which have taken place on November 28th in recent years.
- Mark Polishuk listed the managers and GMs entering the final year of their contract.
- Steve hosted this week's chat.
- Zach compiled the latest edition of Baseball Blogs Weigh In.
- There are many ways to enjoy MLB Trade Rumors. Here's a refresher on how to use the apps, features, and functions on MLBTR.
MLBTR Originals
A look back at the original reporting and analysis found on MLBTR the past seven days:
- The week was highlighted by the Prince Fielder–Ian Kinsler blockbuster. MLBTR's coverage began with Rangers GM Jon Daniels telling Zach Links the deal came together in a matter of hours. Zach also spoke with Tigers President/CEO/GM Dave Dombrowksi, who said the trade makes a Max Scherzer extension "more possible going forward."
- Tim Dierkes opined the Tigers and Rangers will each reap benefits from the swap while Jeff Todd addressed its impact on both the trade and free agent markets.
- Tim sees the Yankees' agreement with Brian McCann (#4 on MLBTR's 2014 Top 50 Free Agents list) as a major upgrade and a sign the team isn't putting their offseason plan on hold while they negotiate with Robinson Cano.
- Tim suggests few saw Jhonny Peralta's (#21) four-year, $53MM contract coming and Stephen Drew (#14) should do better even though he's down a suitor and tied to draft pick compensation.
- Tim believes the Phillies paid an acceptable premium to retain catcher Carlos Ruiz (#29) while the Padres obtained a low-risk, high-reward hurler in Josh Johnson (#30).
- Steve Adams argues the Giants' gamble on Tim Hudson (#31) is worthwhile considering the right-hander's market value compared to the other inconsistent options available.
- Steve isn't as bullish about the Royals' signing of Jason Vargas (#35) because there's little room for upside and four years is an overpay in length of contract.
- Steve profiled MLBTR's top-ranked free agent, Robinson Cano.
- Free agent second baseman Omar Infante (#19) is a good fit for the Yankees, according to Tim.
- Tim was the first to report the incentives in Josh Johnson's contract ($1.25MM for making 26 starts), the Pirates were the runners-up for his services, and the other finalists were all NL teams.
- MLBTR was the first to learn Roy Oswalt plans on pitching in 2014, intends to sign this offseason so as to fully participate in Spring Training, and is open to a late-inning relief role.
- Tim broke the news of the Dodgers signing infielder Brendan Harris to a minor league contract with an invitation to Spring Training.
- Tim heard multiple teams are interested in right-handed reliever Matt Albers with a two-year deal a possibility and learned catcher Henry Blanco wants to play one more season.
- Rex Gary, the agent for Shaun Marcum, told MLBTR the right-hander's recovery from thoracic outlet syndrome is progressing well and will participate in his normal offseason throwing program.
- Mike Moye, the agent for Gavin Floyd, updated MLBTR on the right-hander's rehab from elbow surgery.
- Ibrahim Rojas of CMHS Radio Caibarién told MLBTR a trio of Cuban players (19-year-old pitcher Javier Gonzalez, 22-year-old pitcher Jorge Hernandez, and 25-year-old outfielder Dayron Varona) have left their island homeland.
- MLBTR contributor Matt Swartz detailed the arbitration case of Orioles closer Jim Johnson.
- Steve hosted this week's live chat.
- Zach assembled the best of the baseball blogosphere for you in Baseball Blogs Weigh In.
MLBTR Originals
A look back at the original reporting and analysis found on MLBTR this past week:
- Steve Adams covered the GM Meetings in Orlando for MLBTR and posted interviews with Mets special assistant J.P. Ricciardi, White Sox GM Rick Hahn, and Padres GM Josh Byrnes.
- The Offseason Outlook series concluded with Mark Polishuk's forecast for the World Champion Red Sox while Steve looked ahead for the team Boston vanquished in the ALCS, the Tigers.
- Tim Dierkes expects Juan Uribe to sign a two-year, $12MM deal in free agency while Steve imagines a team will give Jhonny Peralta a three-year contract worth $36MM.
- Tim was first to report the signings of catcher J.C. Boscan and 1B/OF Jamie Romak, both with the Dodgers. He also reported pitcher Michael Crotta signed with the Nippon Ham Fighters.
- MLBTR contributor Matt Swartz provided an in-depth breakdown of the arbitration cases for the newly crowned AL Cy Young award winner Max Scherzer of the Tigers; Marlins slugger Giancarlo Stanton; Rays ace David Price, and relievers Steve Cishek, Ernesto Frieri, Greg Holland, and Kenley Jansen.
- Zach Links gathered the best the baseball corner of the web had to offer in Baseball Blogs Weigh In.
MLBTR Originals
A look back at the original reporting and analysis found on MLBTR the past seven days:
- With tonight's 11:59 PM (CT) deadline to enter the third annual MLBTR Free Agent Prediction Contest fast approaching, you may want to review every installment in our Free Agent Profile series. There were six new entries this week (ranking on MLBTR's 2014 Top 50 Free Agents list in parenthesis).
- Tim Dierkes envisions $150MM over seven years for Jacoby Ellsbury (#2).
- Ellsbury's teammate, Stephen Drew (#14) will garner a four-year, $48MM deal, according to Tim.
- Steve Adams foresees Nelson Cruz (#17) landing a three-year pact worth $39MM.
- Steve anticipates Bartolo Colon (#22) and Dan Haren (#34) both signing for one year and $10MM.
- Tim predicts a two-year, $16MM contract for James Loney (#37).
- Agent Jim Munsey told Tim the Red Sox have called to express their interest in re-signing his client, Jarrod Saltalamacchia.
- MLBTR was the first to learn the Blue Jays would not be tendering Josh Johnson a qualifying offer.
- Steve listed the 13 free agents who did receive qualifying offers.
- Charlie Wilmoth previewed the Offseason Outlook for the NL Champion Cardinals.
- Tim completed the 2014 Arbitration Eligibles series with his analysis of the Indians, Pirates, Tigers, Cardinals, and Red Sox.
- MLBTR has made its projected 2014 arbitration salaries available for download in an Excel spreadsheet. The list can also be found in the sidebar under MLBTR Features.
- MLBTR contributor Matt Swartz explains the arbitration cases of Dodgers ace Clayton Kershaw and Orioles slugger Chris Davis.
- Tim named his non-tender candidates.
- Jeff Todd charted the future salary obligations (2015-2024) for all 30 MLB teams in a two-part series (I, II).
- MLBTR was the first to report the Twins are not interested, at this time, in right-hander Randy Messenger, who is weighing a three-year extension with the Hanshin Tigers.
- Ibrahim Rojas of CMHS Radio Caibarién told MLBTR right-hander Raicel Iglesias, who defected from Cuba recently, is currently in Mexico.
- Agent Felix Olivo told Tim the extension he negotiated for his client, Rangers left-hander Martin Perez, came together in less than two weeks.
- Steve hosted the MLBTR live chat this week.
- Zach Links compiled the latest edition of Baseball Blogs Weigh In.
MLBTR Originals
A look back at the original reporting and analysis found on MLBTR last week as the Boston Red Sox celebrated their third World Championship in the last ten years.
- Tim Dierkes unveiled the eighth annual MLBTR Top 50 Free Agents List and he included his predictions as to where each player will land.
- Where do you think these top 50 free agents will sign? Match your insight against the MLBTR staff and fellow MLBTR readers by entering the third annual MLBTR Free Agent Prediction Contest. The deadline to register (a Facebook account is required) and save your final picks is Sunday, November 10 at Midnight (CT).
- MLBTR's 2014 Free Agent Tracker is now available with the start of the free agency spending spree only hours away. It can be found in the Tools drop down menu at the top of the page or in the sidebar under MLBTR Features.
- There were seven installments of MLBTR's Free Agent Profile series this past week.
- Steve Adams expects Matt Garza will receive a four-year, $64MM contract, Fernando Rodney will collect $18MM over two years, Marlon Byrd's payday will be two years and $16MM, Jason Vargas will net a three-year pact worth $28.5MM, and Phil Hughes and Justin Morneau will try to re-establish their value with one-year deals ($8MM for Hughes and $7MM for Morneau).
- Tim estimates Suk-min Yoon will sign for two-years and $10MM, as he makes the jump from the KBO to MLB.
- I previewed the upcoming offseason for the Brewers and Athletics.
- Jeff Todd and Mark Polishuk summarized the winter ahead for the Braves and Orioles, respectively.
- Tim continued the Arbitration Eligibles series with a look at the Rangers, Athletics, Braves, and Dodgers.
- MLBTR contributor Matt Swartz broke down the arbitration case of Braves closer Craig Kimbrel.
- Tim has compiled a calendar of hot stove events, as the offseason is now in full swing.
- MLBTR was the first to report White Sox left-hander Hector Santiago had hired a new agent: Jim Murray of Excel Sports Management.
- Tim hosted this week's chat.